My first month of purposeful dating meant getting stuck somewhere between the apps and real life

Sure, dating can be fun. It can also be stressful, confusing, heartbreaking, weird, and…boring. But we still do it, and we want to know how you do it, too. In our series “Adventures in Dating,” one writer documents their love life for three months, and we get a peek into every part of their experience—the fun and the frustrating. Starting us off is N.Y.C.-based sex writer Shelby Sells, who will be telling us all about her summer. (Catch up with Shelby’s summer journey in her first piece for the series here.)

Welcome back to my so-called dating life. June was a very wild and transformative month. I went to a nude resort in Jamaica, downloaded almost every dating app, and got the tea on some potential hotties. Overall, I feel very grounded and confident in preparation for the blessings the universe has in store for me (be it model boys in their early twenties, the fuck of my life, or the love of my life).

First and foremost, I need to spill about my time spent at Hedonism II in Negril, Jamaica. Hedonism II is a pleasure-centric clothing-optional resort dedicated to ensuring its guests have the time of their lives. I can’t even begin to explain how good those five days were for my mental health. I had absolutely no idea what I was getting myself into, but I was definitely along for the ride. What do you even pack to wear at a nude resort?! Challenge accepted.

As a self-proclaimed nudist (as you may have seen if you follow my IG), I was eager and nervous to let it all hang out on vacation. My nudist colony at home consists of me, my plants, and my Rick and Morty plushies (who technically have clothes on), so I was admittedly feeling shy at first arrival. But let me tell you, after the first night, I felt completely carefree. The environment Hedonism II curates is safe, sexy, and fun. It was comforting that there were people of all ages (especially the giant group of 20+ hotties in from Canada) who were all comfortable in their own skin. Most people wore lingerie and other limited clothing, if anything at all.

Besides age, there was also diversity in race and body type amongst the Hedonism crowd. Some people had been to the resort over 30 times! It turns out most people who go to the resort are return customers, which speaks to the one-of-a-kind experience you get from this magical place. Another perk was that locals came during the day and at night to party and let loose. It was truly a melting pot of nude people from all over the globe (my own personal heaven?). A major highlight was the foam party in which the resort filled an entire dance floor with soapy foam and it suddenly transformed into a giant freak-fest of dancing, grinding, and making out (I definitely saw some hickeys at breakfast the next day).

Did I mention the playroom? Yep, there’s a playroom that is actually composed of many rooms, all themed for specific genres of play. I peeked into the BDSM room, which was draped in red velvet and complemented by whips, chains, toys, and a leather sex swing. While I am very open with my sexuality, I haven’t fully come around to group sex yet (unless I have the ability to curate it, hehe) so I left the couples and singles in peace to get kinky.

About halfway through the trip, I met a very handsome and built Canadian man whilst clubbing. I believe his first words to me were, “You’re too cute to be here” (re: my anime girl pigtails), followed by, “You have a lot of rhythm for (no offense) a white girl,” which made both of us laugh. The flirty chemistry was effortless and organic. We exchanged info that night and continued to hang out the rest of the trip—which included the time he gave me a lap dance in front of all the guests during a talent show. I’m going to keep it real with you, he put that thang on me! It’s so nice (and a huge turn-on) to be on the receiving end of a male lap dance for once.

Without going into too much detail, my boo snack and I had a very romantic adventure my last night in Negril. We hung out on the nude side of the resort, walked along the beach, and held each other as we stargazed. Did I mention my room had ceiling mirrors? That made hooking up extremely hot. Give me an angle! I want to see it all! I honestly don’t know why ceiling mirrors aren’t more of a thing. My entire experience at Hedonism II was a spiritual awakening to intentionally incorporate more pleasure into my life.

When I got back to New York City, I was glowing.

One of my girlfriends compared my vacation to How Stella Got Her Groove Back, thus dubbing the trip “How Shelby Got Her Groove Back.” I definitely felt renewed and full of sexual, loving energy. In an effort to really try something new and put myself out there, I decided to download some dating apps.

I’ve never been partial to dating apps, though I have seen them work for many of my friends, peers, and colleagues. I guess they always seemed superficial to me—removing intimacy from love and sex, and boxing it up in an easy-to-use, convenient, commercialized box. Yes, I know I’m critical, but in reality, love isn’t always easy or convenient. Previously, I’d made a Raya account, but I didn’t want to continuously pay for the services. This time, I downloaded as many apps as I could that were recommended from friends and the App Store. Raya, Hinge, Coffee Meets Bagel, and Bumble made the cut. I set up profiles on each, eager to get my feet wet in a new dating pool. While the process was a bit tedious, I appreciate the thoroughness and approach of each app.

Over the next week, I had a handful of anxiety attacks. Turns out the impersonal nature of dating apps just does not sit well with me. Maybe I overreacted, but I was raised to never judge a book by its cover, which is the literal plan of action in this environment. Also, any situation that totes the line of forced social interaction makes me super uncomfortable. I scoured the internet on each app in search of even one guy who semi-interested me with little to no luck. It seemed like Hinge, Coffee Meets Bagel, and Bumble all wanted me to be with a 30-year-old dude named Brock who works in finance, still goes home to Staten Island to have his mom do his laundry, and has literally no idea what or where a clitoris is. Again, maybe I’m being a bit harsh, but this character is the furthest thing from “my type.”

I kept Raya because (1) I’d paid for the month and (2) The dating pool seemed more aligned with the creative kinds of people I usually date. Raya is known to be somewhat of an “elitist” app (you have to be approved to be allowed on), but it still operates similarly the way most dating apps do, or so I’ve heard. I matched with a handful of people, and being my shy self, waited for them to initiate conversation. Most did not, which is totally normal, but a few did and I was excited to see whom I’d attracted.

A contender emerged with a straightforward and complementary approach. He said he’d read some of my work and liked it, and he wanted to know if I’d like to hang out sometime. This is exactly how I like to be approached on a dating app.

This guy looked familiar to me for some reason, but I couldn’t place him. I racked my brain until it hit me… One of my girlfriends used to hook up with him. I followed up with her to get the tea. She told me they had hung out just two weeks prior and that he’d also been hitting on some of her friends from work. The way she described him didn’t paint him in the kindest regards, and she was obviously still seeing in him some respect, so I put the kibosh on that date.

After our talk, she texted to thank me for reaching out to her before going on the date. I want to be completely transparent: I sometimes feel dating is set up to pit women against each other in hopes of winning the man’s attention. This is complete and utter bullshit. However, we do live in a big city and, sometimes, paths cross. There have been instances where I’ve hooked up with someone, and then a while later, a friend asked me if it was okay for them to go on a date with that person. And I was totally fine with it—shit happens and we don’t own our lovers/previous partners. They are not our property.

When it comes to dating in shared social circles, an honest approach goes a long way. Friendships are valuable and should be cherished. Asking a friend first saves a lot of hurt feelings. (Of course, every situation is unique. But in my case this time, I’m glad I checked-in before meeting up with my potential date.)

Whew! Thanks for following up with me on my initial month of purposeful dating. I have some exciting things lined up in July and have been meeting some interesting people out at parties and group settings. Looking forward to continuing my journey with you. More soon. xx

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