Sam

Being  somewhat of an Instagram personality, I get guys in my DMs (that’s “direct messages” for those unfamiliar) pretty much on a daily basis. The majority of the messages are some form of flirting, but usually from guys that, I’ll be perfectly honest, I’d probably never go out with. Truth be told, half the time I don’t even read my messages because I’m almost positive they’ll be something weird, a dick pic, or some foreign man asking to see my “bobs and vegana.” But then, every once in a while I’ll see a message from a guy who looks like there’s a chance he could be attractive, so I stalk his instagram account (if it’s public) and determine whether or not I want to answer.

 

Bro tip: if you slide into my DMs, make your profile public. You’re far more likely to get a response that way.

 

After a disappointing couple of days being let down by a couple of men I’d been interested in, I resolved to spend the Fourth of July alone on the beach, which was equal parts depressing and liberating as I love fireworks but people can be annoying. I was scrolling through my messages when a DM from Sam popped up. He was drunk and partying with his friends in San Francisco, but he lived in the South Bay near me and wanted to take me out for drinks when he was back in town. Naturally, I played hard to get and engaged in some playful banter while I carefully and methodically stalked his entire Instagram account to determine if he was cute or not. He didn’t have a ton of photos of himself and the few he had were mostly him making ridiculous faces, so I really couldn’t tell much other than he had the bald and bearded thing going on and appeared to be in shape, but I figured why not. At the very least I’d get some free drinks out of the deal and maybe a dinner and a friend.

 

Once Sam was back in town he asked if I wanted to go to Strand House in Manhattan Beach at 8pm. Not really my vibe, and since 8pm could be a drinks time or a dinner time, I casually asked “are you feeding me or should I eat first?” Sam laughed and said he’d be happy to feed me and suggested going to Fishing With Dynamite instead. Considering that’s my favorite restaurant in Manhattan Beach and I love oysters, Sam was already winning some points, so couldn’t help but respond so politely with:

 

“So are you actively trying to fuck me, or…?’

 

He laughed and said “well, yeah obviously” and we agreed to meet at 8. I never really get super excited about dates, perhaps out of self-preservation or just because I’m a bitch, but I was at least looking forward to oysters and possibly some dick. I threw on a casual beach dress and headed to the restaurant, which I arrived to early but Sam had the foresight to make a reservation so they seated me right away. I sat down and ordered a glass of sparkling rose’ (because I can’t be TOTALLY devoid of my basic bitch tendencies) and waiting for Sam to arrive. Just a few minutes passed and he walked in with a huge smile on his face. Sam was cute, not totally my type but I could see he had a couple of tattoos and seemed to have a cool chill vibe about him and the conversation began to flow as easily as it had in text messages. We ordered oysters and a bottle of the same sparkling rose’ I’d been sipping on to get started, and then another round of each, and then more food, and then when we were already tipsy and probably had no business continuing to drink we made the (probably) ill-advised decision to go to Manhattan Beach’s loveliest dive, Shellback’s Tavern.

 

Two pitchers of Kona Big Wave and my rousing rendition of Toto’s “Africa” while it played on the jukebox later, we began sloppily making out at the bar. Gross. I HATE when people do that. But also, when Meredith has had *just* the right amount to drink, her drunken alter-ego Jackie appears and Jackie gives even fewer fucks than Meredith does.

 

Hoe tip: Give your drunk self a different name so you can blame your bad behavior on your alter-ego and not take any responsibility.

 

The bar was emptying and I decided I was going home with Sam. Sam called us a Lyft and we were headed to his place in Redondo. As we’re on our way I begin to ask Sam about his living situation, like if he was in a house or an apartment or had roommates or what.

 

“Um…about that…”

 

Oh god. This was where the ball was going to drop. Not knowing where this was going next he began explaining to me that his lease had ended recently and he wasn’t moving into a new place for a couple of months so he was currently living at his grandmother’s house.

 

Yes. He was bringing me home to his GRANDMA’S HOUSE.

 

What the fuck. He explained that it was a split level house and he has his own entrance and total privacy but he was basically sneaking me in and out like we were in high school. Sober me probably wouldn’t have been too excited about it, but Jackie was drunk and horny and didn’t really give a fuck. So away we went to Sam’s grandma’s house.

 

Once in his room we picked up where we left off and began making out aggressively. As I was only wearing a dress with nothing underneath (I almost never wear a bra or panties) I was naked before I knew it and he was going down on me. I always appreciate a man who gets me off first because I’m not one of those women who regularly cums from penetration. Once I came it was sort of whirlwind of Sam getting undressed and we commenced the sloppy drunk fucking. Sam was pretty average size wise, but I was really too drunk to care either way and as we went from position to position Sam started with the ass play. I was totally down to get weird and gave him the green light, and just like that, we were doing anal on the first date. It wasn’t long before Sam was ready to cum, and I guess Jackie was really taking over that night because I told him to cum in my ass…so he did. Anal creampie on the first date, my mother would be so proud.

 

After the awkward cleanup that is always associated with an anal creampie, it was definitely time to pass the fuck out. After some solid drunken sleep, we woke up around 8 or 9 the next morning and Sam kindly offered me a ride home and some breakfast. I mean, a gentleman always buys a lady breakfast after cumming in her asshole, right? That like some kind of etiquette rule I think. I don’t know, cotillion was a long time ago. After sneaking me out past grandma and taking me to breakfast, Sam took me home and we agreed we should do it again sometime.

 

My summer schedule was all over the place and we were both in and out-of-town quite a bit, so we never really made it happen again and the appeal faded, but we’re still in touch and always laugh about the first date anal. While the majority of the guys who slide into DMs on Instagram are usually weird, creepy, or just not cute, don’t count them all out because every once in a while you find yourself a cute guy like Sam who takes you out to an expensive dinner, fucks you in the ass, and buys you breakfast the next morning. That’s modern romance, y’all.

 

Accidental Handjob

Back in my former life before memes and telling blowjob jokes on the internet, I used to work in sales in the craft beer industry. One of the many perks I had was getting to travel all over the United States for meetings and trips to our breweries, and my first big girl business trip was to a place I’ve grown to love so much, Portland, Oregon. Portland is basically just like my hometown, Austin, but with cooler weather and mountains in the background, so naturally I fell in love with it as soon as I arrived. It was gorgeous June weather and my coworkers and I immediately began exploring the city and hitting up local breweries. I’d only been single for about 6 months and I was excited to be on my first real business trip, so I hopped on Tinder just to see what I could find. I absent-mindedly swiped here and there for a day or two and came across a handful of viable options, including a super cute hipstery looking guy named Michael. He had sandy brown hair and blue eyes and looked so quintessentially Portland I had to message him when we matched.

 

I had some previous standing dinner plans later that night but Michael was really cute so I thought, why not go back to back and meet this guy for happy hour. I was down for something super laid back with good beer, so Michael suggested a bar called Momo’s and our date was set. I went on with my work day, stopped back by my hotel room to change, and I was on my way. When I arrived at Momo’s Michael was as cute in person as he was in his photos, and had a great and charming personality. He made me laugh, we drank a few beers, and I was laying on the flirtation heavily. You see, most all-day long work meetings can be pretty boring. But when you work for a brewery, you’re drinking during them. So I was definitely around 5 beers deep when I began the heavy petting. What can I say, I’m a classy girl.

 

We began making out a little at our table and I asked Michael if the bathrooms here were single-person ones or ones with multiple stalls, and he said it was a single-person one. I smiled with a look that I can only imagine would either strike fear in the heart of my mortal enemies or give them all intense boners, and said

 

“Perfect. Meet me there in 2 minutes.”

 

And like he’d been using stop watch, Michael showed up to that bathroom in exactly 2 minutes. I locked the door behind him and we went after it, making out, running our hands all over each other and he pushed me up against the sink. I was wearing panties for some odd reason (I rarely ever do this) and he reached up under my dress to pull them down. As he smiled and began kissing my thighs, I propped myself up onto the sink. Michael slipped my thong off, spread my legs and dove face first into my freshly waxed pussy and went to fucking town. It was so hot, the idea of getting caught, propped up on this bar bathroom sink, getting eaten out by this insanely cute guy. It wasn’t long before I was cumming in Michael’s mouth. Fuck, it was so hot.

 

Naturally, I went to return the favor, as is only the right thing to do. I undid Michael’s pants and pulled out his hard dick. Average in size, although not that it really mattered since I was just blowing him at this point. I put him in my mouth and it seemed like MAYBE a minute before he was cumming. I thought, either I’m just that goddamn good or this guy cums quick as fuck. I could tell he was a little embarrassed so I made no mention of the speed or anything, we got ourselves put back together and made our probably very obvious exits from the bathroom and got one more drink before I went off to my dinner plans. Michael was great and I really wanted to give him another shot before I left, so I suggested he stop by my hotel room sometime the next day for another round.

 

The next day, Michael came to my hotel room. Still cute as ever, and this time he seemed very ready to go and roll around a little now that we had some space. We made out for a while and he slipped off the shorts I’d been wearing around my room. Michael was apparently a pussy eating prince and dove in again. I laid back and enjoyed his tongue skills and after I came I reached down to warm him up before sex. Only, there would be no sex.

 

I pulled Michael’s already hard dick out, and within two tugs of a half-assed handjob, his body shook and my hand was full of cum.

 

I hadn’t given a handjob to completion since I was a teenager, nor had I ever experienced a man cumming THAT quickly and easily. I thought he was embarrassed but he just kind of laughed it off and said “oops.” What was this? Some kind of hipster retro handjob sex thing? Damn, hipsters really do have to do everything before it’s cool, including cumming apparently.

 

I awkwardly went to the bathroom to wash my hands and when I came back he was dressed and said “well, have a safe trip home.” I hugged him and said goodbye, and he left. Naturally I told my girlfriends IMMEDIATELY about the accidental handjob I’d just given, and started getting my things together to head home.

 

Maybe Michael cums quickly on a regular basis. Or maybe it was just me. But at least he was cute, funny, and he made sure I came first so I really can’t complain much. We’re still in touch and talk from time to time, he’s still cute, still funny, and still loves eating pussy.

 

Hoe tip: make sure you get yours first, ladies.

 

Jack

I grew up in Austin, Texas, but when my mom remarried when I was around 25 she moved to the Ft. Worth area. Visiting her is nice, but I hardly know anyone there so I get pretty bored during a long visit. That’s where Tinder and Bumble come in handy. I debated whether or not I wanted to swipe right on Bumble on Jack for a minute before ultimately saying “fuck it” and going for it. We were a match, and since Bumble requires the woman to make the first move I went ahead and sent a pretty generic “hey how’s it going” message, and he responded almost right away. It turns out Jack was also visiting his family and just as bored as I was on a Monday evening, and after maybe a few minutes of conversation we decided we both needed to get out of the house and get a drink.

 

Jack wasn’t exactly my type, I’m not usually into bald guys, but he had a great smile, had the whole cute Italian thing going for him, and he looked like fun, so I was game. I met Jack at a bar not too far from my mom’s house, close to Texas Christian University campus (oh the irony), and he greeted me with a huge smile and hug. I could tell he had a good energy about him as we started to talk and get to know each other. Jack was a professor at a pretty well-renowned university who would be spending a few months writing his first book this winter, so we shared war stories of the writing process, and commiserated over the struggles of writer’s block. I told Jack all about my Instagram and my blog and he was enthralled with my dating stories.

 

“I’m gonna do what it takes to make the blog,” Jack said with a smirk.

 

I wasn’t sure if he meant he’d do something terribly embarrassing or if he meant he was going to blow my mind, but either way I was excited to find out.

 

We decided the bar we were at was a little too dead so we needed a change of scenery, so after one beer we hopped in the car to find a more lively spot. After cruising around for a little while, laughing and realizing more and more that we were both total insane people, we pulled up to a dive bar that I can’t remember the name of and parked across the street. It was Monday, so everywhere was pretty dead, with nobody walking around, and before we got out of the car Jack said “I need to kiss you first.” We made out in the car like teenagers for a few minutes, and I knew the rest of the night was going to be fun.

 

Once we finally stopped acting like we were 16 and on a date to the movies, we went into the dive bar and had a couple more drinks. I almost never wear a bra or panties, and this night was no exception. Jack noticed and ran his hand up my inner thigh under my dress, right there at the bar. I tossed back the rest of my drink, looked at him and bit my lip. He smiled, leaned in to kiss me, and kept going with his fingers, teasing me under my dress, and then asked the bartender for his check. It was most definitely time to go.

 

We hurried to the car where we got in and realized, oh shit. We are BOTH staying with our parents right now. Jack was driving his dad’s car, and we couldn’t go back to either of our places, so we had to improvise. Jack drove to a dark parking lot nearby and we crawled into the back seat. It was only at this point that I noticed that the radio had been on this late 90s alt rock station, which only added to the high school nostalgia of the entire thing. Jack and I started going at it, aggressively making out, and he laid me down and pushed up my dress and started devouring me like I was his last meal. It was so hot, and just as I thought I’d cum soon he ripped off his shorts, revealing quite an impressive package and he slid in. He was just the right amount of rough, pulling my hair, lightly choking me and pretty much fucking my brains out. I came hard and as soon as I did, so did he, without missing a beat or even pulling out. While I realize getting cream pied on a first date isn’t exactly the smartest or safest thing I’ve ever done, it was so fucking hot I didn’t care.

 

Hoe tip: if you’re gonna make reckless decisions, at least make sure they’re fucking fun.

 

The windows of Jack’s dad’s Honda Accord were fogged up, R.E.M.’s “Losing My Religion” was on the radio, and I was getting railed out in a back seat in a dark old parking lot. If that doesn’t bring back some teenaged memories, I don’t know what does. We fucked a couple more times (shout out to Jack for having outstanding stamina), and then decided it was getting late and we needed to get home. Jack drove me back to my mom’s house, which just so happened to be in the same neighborhood his parents lived in. We pulled up to my mom’s house, Jack kissed me one more time, and as I got out of the car I said “oh, you made the blog.”

 

Jack drove off, and I snuck back into my mom’s house with cum dripping down my inner thigh, really rounding out my trip down memory lane. I hopped in the shower, and laughed at myself the entire time in there, grabbed some water when I got out and crashed. Jack and I are still in touch, and I’m sure we’ll see each other sometime when we’re both home for the holidays. Can’t wait to make another mess in the back seat of his dad’s Honda Accord.

Andrew

There’s something hot and exciting about a cute guy on the other side of the country wanting to fly you out for a weekend getaway. Promises of nice dinners, maybe a day at a spa, and lots of hot sex—sign me up! That’s what Andrew had offered me repeatedly, but since I only knew him on the internet, I declined. I mean, sure, I’d flown halfway across the country to meet a guy for the first time before, but I took my time vetting Andrew to make sure he wasn’t some sort of Patrick Bateman about to murder me. Andrew followed me on Snapchat for a long time, messaging me here and there, always flirtatious, and I would flirt right back. He was cute, but not really my type—a little too clean cut for me—with blonde hair and blue eyes. The kind of guy who definitely wore pastel Polo shirts with khaki shorts and loafers, but he had a nice body and I won’t lie, his bulge pics were impressive. He regularly asked if I’d like to come visit him in Boston, but I took my time getting to know him.

 

Over the course of several months I learned that Andrew was an accountant for the Navy, lived in a nice area in Boston where he had moved to from Virginia. He and I added each other on Facebook and he offered up any information I asked of him. I began to feel comfortable with him as a person and started to consider his offer to go to Boston. I figured I would make sure everyone knew where I was, and if I began to have a bad time then I could always leave or make friends in Boston and explore the city on my own. I was no stranger to enjoying a city on my own or meeting new people, so I thought I’d roll the dice and take him up on his offer. Andrew and I agreed on a weekend in July and he booked my flights for me. He told me that we would go out to Nantucket or Martha’s Vineyard one day and that we’d have a great time. He also said that he may have to work a little bit one day, so he’d gladly send me to a spa while he was busy. I was totally excited about my weekend trip and when the day came for my 6 hour flight I was more than ready for an adventure.

 

I arrived in Boston on a Thursday night and Andrew said he was outside waiting for me in his Audi. Nice car choice, Andrew. I was nervous and excited as I walked out of the airport and quickly spotted him. He was a little shorter and skinnier than he’d appeared on Snapchat and in his pictures, but I guess we all know our angles. He helped me with my bag and we were on our way to get dinner. It was a little awkward, he wasn’t outwardly affectionate, but he was very complimentary, telling me how sexy I was and how he couldn’t wait to get me home. We finished dinner and headed back to his place. When we walked in the door I noticed it was a pretty big space and he mentioned that he had a roommate. I asked if his roommate knew I would be there and he laughed and said “Shit I probably should’ve mentioned that to him.”

 

I thought it was weird he hadn’t told his roommate that he’d have some girl staying with him for the weekend, but maybe they weren’t close or maybe he knew he wouldn’t care. I don’t know, I was just ready to have fun. We went into Andrew’s room and got situated and he started to kiss me. We began to make out, which was decent, and he started to feel me up a la high school make out, before moving on to removing my clothes. As things started to heat up and we lost more and more clothing, I noticed that his dick wasn’t as big as it had appeared in his bulge pics.

 

This, my friends, is called cockfishing.

 

The dick didn’t match the pics, but it was relatively average. Andrew grabbed a condom and we got down to business. We pretty much just stayed in missionary and the sex didn’t last all that long, but I did manage to get off so it was fine. Almost immediately after finishing and tossing the condom, Andrew fell asleep. I was still on west coast time and it was only like 9pm so I was bored and just messed around on Instagram until I crashed out too.

 

The next morning Andrew woke up early and went to get breakfast for me before he had to go into work for a little while. I didn’t mind because I was a little jet-lagged and needed a nap, plus I had some work to do on my computer. It was raining in Boston so it wasn’t like I wanted to walk around the city, but Andrew was kind enough to leave me some cash just in case I felt like going to do something solo. Because of the weekend’s weather, we were no longer going out to Nantucket but he said we’d do fun things in the city. I was a little bummed, but I couldn’t do much about the weather. Later in the day he was finally headed home and asked what I’d like to do that night and if I wanted to get dinner and drinks. I said yes.

 

Andrew got home and seemed a little off. I was ready to go to dinner and he was quiet and not as complimentary as he had been the night before. Finally he asks me, “What did you snapchat today?”

 

I looked at him with confusion and racked my brain. I hadn’t snapped anything crazy, just a few shots of me with stupid filters on saying that I was in Boston. He told me not to snapchat from his house anymore, which was confusing and weird. I asked what was up.

 

“So, I’m dating someone. And it turns out, she follows you. She recognized my bedroom in the background of your snaps.”

 

Motherfucker.

 

He quickly tried to do damage control and tell her that I’m just a friend crashing with him for the weekend and that it wasn’t anything to be worried about. But then he told me what her snap name was and said not to open any snaps from her if she messages me. I asked if it was exclusive or what the situation was, and as he tried to downplay the relationship to make me be cool with things. I began to realize that no, this guy is obviously a liar, and this wasn’t okay. He then proceeded to go into his living room and ignored me for three fucking hours, like as if somehow any of this was my fault.

 

Hoe tip: when a guy gets caught cheating on his girlfriend, it is HIS fault.

 

I had received several messages from people in Boston wanting to hang out and I got on Bumble and said fuck it, I’ll find someone else to hang out with this weekend. As a few hours went by a guy I’d talked to several times in recent days, Jay, offered to pick me up and at least give me somewhere else to crash for the night since it was late at that point and Andrew hadn’t even had the common decency to feed me dinner (after feeding me bullshit, that is). I texted Andrew from the next room and told him I was leaving. Andrew came into his room and asked if I was sure, and I told him that I was really uncomfortable and didn’t want to be there anymore. He gave me a half-assed apology, Jay showed up, and I was on my way.

 

Jay took me for a drink and a bite to eat with his friends, and gave me a place to crash for the night. He showed me around Boston a little the next day, and then we went our separate ways. I set off to meet a guy or two from Bumble, after, of course, Jay decided to go out of his way to tell me that I don’t contribute anything to society and that I’d be cuter if I took better care of myself. Like completely unprovoked, he felt the need to pinpoint everything he thought was wrong with me. The next guy I met in Boston, Adam, was all fun and great and invited me to drinks and dinner with his friends, but ditched me after drinks to wander around south Boston alone. I got myself a room, had a good cry, and crashed out.

 

Finally it was Sunday and it was time for me to go home. I couldn’t wait. I got to the airport, got on the plane, and got shit-faced. Andrew had bought me an upgraded seat that included complimentary alcoholic beverages, and I took full advantage by drinking all the prosecco they had on the plane. As I was crushing drinks I thought about all the people I had encountered over the weekend. Every guy started out with promise and just wound up being a typical, immature dick. What kind of vibe was I putting out there that I was attracting these guys? I mean, sure I portray myself in a certain way, but that doesn’t mean I’m not still worthy of respect as a human being. Andrew probably assumed that because I’m a sexual and open person, I would be okay with facilitating him cheating on his girlfriend. And Jay probably thought that I somehow needed his advice on how to live my life because I’m a woman and therefore inferior to him (I almost sprained my eyeballs rolling them so hard). And as for Adam…well I think he just got drunk and forgot how to treat people. At the end of it all, these men were immature and lacked respect and that wasn’t my fault.

 

I don’t think I’ll ever be making it back to Boston. Although I’m sure there are plenty of lovely people there, I only met Massholes.

Ask Meredith!

Time for me to give more shitty advice!

 

Q: I’ve been dating my girlfriend for almost two years now. She truly is awesome. She’s funny, pretty, and I know has my back through anything and everything. And of course I am totally in love with her. As awesome as she is I have been super tempted to cheat on her. I have two girls right now that are just waiting for a text from me. I really want to but at the same time am very hesitant because I know if she were to find out what I did it would absolutely devastate her. I don’t know if I should go through with this or not. I know losing her in the long run definitely isn’t worth it but I miss sleeping with random chicks and not having to deal with all the things that come with being in a relationship.

A: If you love your girlfriend and don’t want to lose her, don’t cheat on her. It’s not fucking rocket science. If you want to fuck other girls, break up with your girlfriend. But don’t be surprised if you find yourself missing her and she doesn’t take you back. Pretty simple if you ask me, keep your dick in your pants if you want to keep your girlfriend.

 

Q: I know you always say you don’t want unsolicited dick pics, but I know sometimes girls ask to see it. When would you want to get one and how should a guy send one?

A: This is a good question. I can’t speak for all women, but I do think that I can for the majority when I say that you should never send a dick pic unless a woman asks you to. For example, if I’m sexting or flirting with a guy and he tells me he’s turned on I might ask him to show me–acceptable time for a dick pic. Or if I’m interested in sleeping with a guy I might ask to see what he’s working with. Another scenario is if I’m exchanging sexy pics with a guy and he sends me a full body pic where is dick is exposed–that would be fine. As for tips on your dick pic–include your body in the pic. Just a dick is aggressive. Don’t make it zoomed in too close, and if you take it from the bottom up that’s a tell-tale sign you’re trying to make it look bigger. Also, let’s start being honest about what 8 inches is, okay fellas?

 

Q: What does it take to get a date with you?

A: This is a common question in my DMs. If it’s just a date we’re talking about, be attractive, between the ages of 27-45, have a decent job, and be a non-smoker. The smell of cigarette smoke makes me want to throw up and second-hand smoke makes me cough (on account of the asthma). Weed smoke doesn’t bother me though. Make me laugh and have the ability to make me cum. If you’re asking me out, dinner/drinks/whatever we’re doing is on you my man. Also, I’m 32, not 21, so put in some effort with where you decide to take me. That doesn’t mean it has to be expensive, but make it worth it for me to go out with you. Also be geographically desirable, I’m not traveling more than like 30 minutes to go on a first date. I think that sums it up pretty well!

 

Q: What is too small for you when it comes to dick size?

A: My preferred range is 7-8.5 inches, however I’ve had perfectly good sex with someone in the 6 inch range. Under 5 and you better have a strong head game my friend.

 

Q: I really want to blow my boyfriend’s mind with a great blowjob. I think I’m okay at it, and I usually make him cum unless it’s foreplay before sex, but I want him to be super impressed. Any tips?

A: The biggest keys with giving blowjobs are to pay attention to your man’s responses to whatever you’re doing, and to enjoy it. Notice when his breathing changes or intensifies–he likes what you’re doing. Spit on it. Don’t be afraid to get messy and use a lot of spit, guys like a messy blowjob. Also get your hands in on the action, using a slightly circular motion on the base of his dick while you use your mouth so it’s kind of like your hand is an extension of your mouth. Keeping a steady rhythm once you can tell he’s getting close will make him cum—don’t change your rhythm up too much (unless he’s into edging and you want to prolong the process—that’s another topic). If you’re able to deep throat that’s a fun thing to do while you’re building him up. If he enjoys face-fucking you then being able to deep throat is a must. Relax your throat and breath through your nose. A good finishing move when he cums is licking his dick hole—the tip and hole are super sensitive so definitely give that area some good attention. Most of all, have fun! You’re always likely to be better at something you’re having fun doing, and he will notice that you’re having a good time and enjoy it more. And don’t forget, spitters are quitters (unless he prefers a facial or something). Good luck!

 

That’s it for this week! If you’ve got burning questions for me use the contact submission form or email me at meredith@meredithactually.com!

Xoxo,

Meredith

Ryan

Dating apps can be a real bitch sometimes. You match with someone and then they don’t respond to your message. You match with a guy and he says he’s only in town for that day and you’ve already got plans. You match with someone, talk for a few days, and then it fizzles out. Or you can match with someone just visiting the day they’re leaving town, have a great conversation and get totally bummed that you’ll probably never meet each other.

Probably being the key word here.

Ryan and I matched on Tinder back when I lived in Austin. He didn’t have much information in his bio, but he was cute with brown hair, blue eyes, and an infectious smile. When he messaged me it was basically to say “Oh noooooo! I’m leaving town today and you’re really cute!” As it turned out, Ryan was just in Austin for a few weeks working at a summer camp he volunteered at every summer for underprivileged youth (swoon). He was originally from Scottsdale, Arizona, and went to college in San Diego, where he was headed post-Austin on his 3 month break from teaching English at a school in Colombia. Yeah, as in the country. This cute, sweet Jewish boy from Arizona was fluent in Spanish and lived in South America.

 

Well fuck.

 

The conversation with Ryan was as easy as if I’d known him my entire life, and he seemed to be one of the kindest, most genuinely good people I’d ever spoken to. He played in a band in Colombia, wanted to go back to school for music therapy, and didn’t seem to have a negative bone in his body. We began texting every day, moving into phone calls, and then FaceTiming. Ryan was spending some time in San Diego visiting college friends, and then back to Scottsdale for a few weeks to see his mom before returning to Colombia, and it became more and more frustrating knowing that we would never meet each other. That didn’t stop us from talking constantly and getting to know each other more and more though. There was definitely a connection there, something worth exploring, but to what extent?

One night as Ryan and I were texting about his move back to Colombia, I couldn’t help but feel sad about it. It was like as long as he was on the same continent I had some sort of chance to see him, but once he went back to Colombia it was all over. It’s a weird feeling, missing someone you’ve never actually met. And then I got this insane idea.

What if I went to Arizona before he left?

I was traveling quite a bit for work leading up to this point and had bunch of airline miles to use, and I’d also accrued quite a few hotel points, so I thought why not? If things went south I had a friend who lived in Phoenix so I wouldn’t be all alone, and if things went great then cool, we’ll have a good time. So I pitched it to Ryan, and after we both got over the fact that me getting on a fucking plane for a Tinder date is absurd, we both decided that we’d regret it if we didn’t. We looked at our calendars and figured out the weekend before he was going back to Colombia and I booked my flights.

Holy fuck. I’m going to fly from Austin to Phoenix for a weekend trip with a guy I have never met in real life.

As we began to plan our weekend, Ryan suggested driving up to Flagstaff and spending the weekend there, so I booked a room there. I was beyond excited for the trip. I had no concept of where things in Arizona were at the time as I’d only briefly been to Phoenix once on a business trip, so I pulled up Flagstaff on Google maps and realized the Grand Canyon wasn’t far from there. I excitedly brought it up to Ryan and he said he was game to make a day trip of it. How many people can say they went on a first Tinder date to the Grand Canyon??

As the weekend got closer, I realized I should probably tell someone where I’m going. I made up a story to tell my mom about going on a team building trip for work, but then I decided it was smart to tell my best friend Rachann the truth, just in case.

“Jesus Christ, Meredith, well when you wind up having a Dateline episode about you being thrown into the Grand Canyon never to be seen again I’ll be sure to say nice things about you.”

Ryan and I had added each other on Facebook at this point and I gave all of his contact information to Rachann. She is basically like having a private investigator for a friend, so he was properly vetted and deemed safe, and before I knew it I was on my way to Arizona.

I nervously had a few drinks on the plane and kept in touch with Ryan about my ETA. My heart felt like it was going to beat out of my chest as I landed and began to walk through the airport to meet him. I told him where I was as I walked outside and he pulled up almost right away. He got out of the car and it was like the entire world stopped. I was moving in slow motion as I walked toward him. We were both smiling like idiots and Ryan was obviously as nervous as I was. We hugged and he helped me with my bag and we hopped in the car. It was totally surreal finally seeing him in person and sitting next to him in the car. Once the initial shock wore off it was like we’d known each other for years. We talked and laughed and had a great car ride up to Flagstaff, where we checked into our hotel and figured out our dinner plans.

Once we got to our hotel room, Ryan kissed me. He was a great kisser, very soft and sweet, and before I knew it he had me laying on the hotel bed and working his way down my body kissing me everywhere until he was face down between my legs. Everything about him going down on me and then having sex with me was sensual and romantic. He was definitely a pleaser and a lover, and I couldn’t wait for the rest of the weekend with him. The sex was nice. Nothing super wild, no crazy positions, but the kind of sex where you felt safe and cared for and he made sure I came a couple of times. Wild animal sex is fun and all, but sometimes the slow sweet stuff is all you need.

That night we just got dinner at the hotel, had sex again, and crashed out so we could get up early for our day at the Grand Canyon. Ryan sweetly woke me up in the morning by going down on me, which, let’s face it, is the only acceptable way to wake a woman up before 8 am as far as I’m concerned. After properly sexing each other up that morning we got breakfast and were off to the Grand Canyon. The drive there took maybe an hour or so and like a sickeningly sweet couple from a Rom Com we held hands in the car and sang along loudly to the radio. I almost gross myself out thinking about it, but I was seriously on cloud 9. It was a little chilly and overcast that day, with a slight chance of rain in the afternoon, but I couldn’t have been more excited. Once we parked, we walked into the park and then there it was.

If you’ve never been to the Grand Canyon, my description and pictures you see online cannot do it justice. It is truly unbelievable and breathtaking, and the fact that I had the most amazing company only made the experience more incredible. We walked along the trail and I couldn’t stop taking pictures. It finally began to rain a little so most people went inside the gift shop, but we stayed outside and just the hoods of our rain jackets up. We realized that we were all alone there at the Grand Canyon, in the rain, and we started making out. We were so lost in the moment that we didn’t even realize when the rain let up and that people had come back outside for a few minutes, but when we did we looked back out at the canyon and saw clouds filling in below us and a rainbow shoot across the sky seeming to come out of the canyon itself. It was like something from a movie.

We were ready to head back and get it on, all horned up from the rainy makeout session, so we made our way back to Flagstaff to shower and bang again before heading out for the night. We found a cool little brewery that also had a pizza food trailer there, which are two of my favorite things in life, and had a few drinks before Ryan took me up to this lookout point up on the side of a mountain in Flagstaff. I don’t know if it was the couple of beers we’d had, the fact that we were still reeling from the day, or the little bit of weed we smoked, but I’d never had a more intense makeout session in forever it seemed. There was just some chemical connection we had and we knew it was time to go back to the hotel for another night of intense, romantic sex. Eye contact, hands in the hair, slow grinding, passionate sex for what seemed like hours.

Sunday morning we lazily got up and got ready to check out of the hotel. We wanted another early start so we could spend the day in Sedona before my flight home that night, and the feeling of sadness that the weekend was almost over started to creep in. After having sex one last time we checked out of the hotel and began our trip to Sedona. We were stupid and cheesy again, holding hands in the car, and not saying a word but not needing to. We were so weirdly connected. We arrived in Sedona and did some hiking and once again, it was incredibly beautiful. I really had no idea before this trip that Arizona had that much more to offer than the desert, and I was pretty impressed. We stayed in Sedona as long as we could, enjoying each other’s company, until finally it was time to head back to Phoenix.

On the car ride to Phoenix I received a text notification that my flight was delayed an hour, so we stopped at a bar near the airport. We were so happy to get another hour together, and then I got another notification, 30 more minutes delayed. Then another, 30 more minutes. First time I’d ever been thrilled to have a flight delayed multiple times. Finally the notifications stopped and this time it was real, I had to go to the airport. We didn’t say a word in the car, but this time it wasn’t because of the high on life, heart-eye emoji feelings, it was because we were both so sad for the weekend to be ending. Neither of us expected it to be this way. We both just thought we’d have a fun weekend and that was it. Once at the airport we hugged and kissed one last time and I could feel my face getting hot and my eyes welling up with tears. Ryan told me we’d see each other again someday, and thanked me for an amazing weekend, and I walked into the airport. The tears started to spill down my face as I went through security and I just kept my head down and was on my way to my gate. Once I boarded the plane I grabbed a window seat, which I never do, I’m an aisle seat kind of girl, and put my headphones in. I rested my head against the wall of the plane and slept through the flight (another thing I never do). I let Ryan know I’d landed, went home and immediately downed a glass of wine and crashed out.

Ryan left for Colombia a couple days later. We kept in touch via social media and I even considered coming to visit him there. But time went on and we both lived our lives and the contact became more sporadic and we moved on. I hear from Ryan from time to time, I think he has a girlfriend now and seems to be doing well and really happy. What started as just looking for a good time and a little fling turned into meeting someone who will always hold an important place in my cold, icy heart, and I’m so grateful for the time we spent together.

Hoe Tip: sometimes the risk is totally worth the reward.

Be My Crush!

Starting TODAY I’ll be selecting one lucky guy and one lucky lady each week to be my #ManCrushMonday and #WomanCrushWednesday (respectively). Want to be my crush? Want your pic on my IG? Want to nominate someone you think is pretty great and needs to get laid? Send you or your nominee’s name, short bio, IG handle (must have a public IG account), and a picture (no nudity please), and I’ll notify the lucky guy/girl on their respective crush day! 18+ only, please send submissions to me at meredith@meredithactually.com with “MCM” or “WCW” in the subject line, or you can use my contact submission form. Good luck!

Xoxo,

Meredith