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My experiences with online dating can be boiled down to the captivating and seemingly contradictory X-Files mottos: “Trust No One” and “I Want to Believe.” Through my love/hate relationship with OkCupid (Hi, OkCupid. I am open to sponsorship deals, but would rather avoid any lawsuits.) I’ve become too jaded to believe “The Truth Is Out There” on that blue and pink website (who did the web design? It looks like a children’s nursery) but the dating platform has certainly provided me with more strange tales and sexual tension than Mulder and Scully. Here are my top 10 interesting experiences and yes, X-Files is my higher power:
1. The well-dressed British man who loved motorcycles and took me out to a proper English tea for our first meeting. The date was polite in theory, but the request to stick my pinkie up his urethra was not. As someone pro-kink I don’t judge him for his sounding needs, yet the request came far too quickly and there wasn’t chemistry to begin with. No romantic or sexual exchanges occurred as a result.
2. The lawyer who took me out to dinner and said on repeat that he liked me because I reminded him of Britney Spears. This was three years ago during my wild years, so unless he’s referring to shaved-head Britney, I don’t think this dude listened to a thing I said. This taught me an important lesson in online dating: Never accept an invitation to dinner as a first date. Start with drinks.
3. The dude who began his message with letting me know he just got out of solitary confinement. I’d be lonely after that too, bro.
4. My first true sexual experience with a woman. She was lovely. It was lovely. No further comment out of respect for this creature of beauty. If you are a straight woman watching a lot of lesbian porn and wondering if it’s time to explore in real life, Internet dating is a wonderful way to find people.
5. My very first OkCupid date upon moving to New York City, and doing drunk yoga and being taught how to use synthesizers in his basement East Village apartment while he created a track titled “Sophie.” Things never developed romantically with this guy, but we stayed in touch and are friends to this day.
6. The fellow sober musician who wore eyeliner (hot) and took me out for Mexican food (a favorite cuisine of mine). It could have been a perfect date except he brought a fucking chaperone. We both ordered virgin Margaritas, but when the chaperone got up to use the bathroom and it was just the two of us, he reached across the table at the restaurant and attempted to grab my boob through my Angelina Jolie tank top.
7. That time I went on a first date in a cemetery with someone I’ve interviewed for another publication whose alias is after a serial killer. We had a week of adventures in New York City together, and I ended up flying to another city to see him. He’s still an important person to me to this day.
8. The resulting messages in my inbox asking me out on dates in a cemetery after OkCupid users stumbled upon my interview with previously mentioned person of interest. A cemetery actually is a rather romantic stop for a first date, but the copycats who recognized me and used my article to try and get laid freaked me out.
9. That time when I went to a date drunk, expecting nothing, as a result of all these other horrible dates, and then ended up meeting someone I dated for two and a half years and lived with. Although things didn’t work out between us, there will always be a place in my heart for him, and I wish him nothing but love. Long-term relationships can and do happen (I just know someone who got engaged!) from Internet dating.
10. That other time I met someone in real life, quit Internet dating, and wrote an entire article about it, but that didn’t work out so now here I am writing about OkCupid again. What you should take away from this is that dating is hard—on or off the Internet—and never to take me entirely seriously. Also, if you do see me on a dating site, I would probably not message me, as my attention is currently far more focused on writing than finding an OkCupid date, but damn you motherfuckers make for some great writing material.
Reprinted with permission from The Style Con. Want more?