I'm Willingly Getting Into Trouble [Diary of the Undateable]

I’ve been embracing the spirit of going with the flow – something that I was previously VERY against – ever since I moved back to New York. I mean, I figured that there are too many cute men to stick to my sometimes-silly standards. Relax and live a little, she said. It’ll be fun, she said. You won’t get hurt, she said. And true to her nature, she’s dumb as hell for thinking that.
OkCupid had some pretty cute guys during the few days that I reactivated my profile. Tall, short, skinny, buff, French-vanilla, butter-pecan, chocolate-deluxe. Instead of changing my profile picture every few hours and editing my bio in hopes that someone would message me, I reached out to guys that caught my eye. I had nothing to lose, really.
I don’t know how I found this one particular bespectacled cutie, but I was glad that I did. I’m a sucker for glasses since I wear them myself. He was super duper tall (and thank the high heavens for that – I’m sick of dating guys shorter than me), an artist/substitute teacher/photographer/burrito enthusiast. Loves kids? Loves selfies? Creative? And down for Chipotle? Check, check, check and check. I’ll call my crush Big Kid – because that’s what he is. But I’ll get to that later.
Big Kid seemed really genuine. On his profile, he listed reading as one of his interests, so I asked him what book he was into at the moment. Our conversation was pretty good, albeit one-sided. Still, I thought. Why not? He’s obviously interested if he answered. So I gave him my number. We started texting on a Sunday.
“What are you doing?” he asked me after hitting me up. “Because I’m having very dirty thoughts right now…”
Damn. I should’ve known that he was a creep. But actually…how could I? It wasn’t something immediately apparent. He even said on his profile that he wasn’t looking for casual sex. So why was he opening up our conversation with thoughts of that?
I politely expressed my discomfort, and he apologized immediately.
“I’m so sorry. I’ll chill,” he said. “I just have a proclivity for dirty thoughts…and I’m really attracted to you.”
He had me at “proclivity.” I’m a sucker for SAT words.
Big Kid toned the dirty talk down for the rest of the afternoon but, like clockwork, picked it up the next day. He only wanted one thing. I should’ve tossed him into the undateable ether, but I decided to make a choice…one that I’m not too proud of. I definitely wasn’t going to have sex with Big Kid because a) I didn’t know him, b) I’m still trying to wait and c) he slightly creeped me out – but I wouldn’t mind hanging out with him and making out. You know, because I’m obviously in sixth grade.
I told him what I wanted and my hard limits. He was down. We made plans to meet up at Union Square Park later on that week, Wednesday. He cancelled on me that afternoon, saying that he lost his wallet. Bull. Shit. I promptly ignored him and kept it moving. But he apologized profusely, and we rescheduled for Saturday.
So Saturday comes, and we meet – though he’s like 45 minutes late, but whatever. Other than that, it was really nice. He was really nice. And cute. Really cute. His Batman hoodie matched his Jordans and Brixton snapback – I remember appreciating his attention to detail. More importantly, though, he was funny and a gentleman. He made sure to hold doors open for me and made sure that I was on the “safe” side of the street. Despite the rat that scurried in front the park bench where we sat, it was a nice night.
“So what are you looking for?” he asked. The inevitable first date question that I always rehearse but never quite express properly.
“I want someone consistent,” I answered. “I don’t think that I need a boyfriend at the moment, but I still want someone to hang out with and talk to. Someone who wants to work towards a relationship rather than rush into one.”
“Ahh, okay,” he replied. “That kind of sounds like you want a Friend With Benefits.”
I’ve heard many interpretations of what a Friends With Benefits relationship is. Some say that it’s a purely sexual relationship – one that’s just about the physical. No emotional connection whatsoever…hit it, quit it, forget it. But I’ve heard other instances where your Friend With Benefits really does end up being a confidante…all the fringe benefits of a relationship without the drama, attachment and messiness.
In retrospect, since I’ve never been in a relationship, a Friends With Benefits situation probably wasn’t the healthiest thing for me. I’m still learning about relationships to begin with…and a partial one just wouldn’t be a good look. But Big Kid was so nice. So funny. So smart. And so damn cute.
We shook hands and agreed to be Friends With Benefits. The handshake made it official. The kiss sealed the deal, though. I knew that messing with Big Kid would get me into bigger trouble…but it’s basically summer which makes that okay, right?
Yeah, yeah. I know. Wrong.
When she’s not watching for Blue Ivy sightings or doing some serious Facebook creeping, Khalea, a recent Howard University graduate, moonlights as a magazine intern and a freelancer in New York City. Follow her on Twitter at @letsbeKHAlear, or feel free to Twatch. Whatever works for you.

Lesson #20: Just Get Up and Move On [Bold Girls' Bible]
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