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.

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.