On my twenty-ninth birthday, I wake up in bed with my boyfriend’s friend. Off to a smashing start! OK, to be fair, he’s not my official boyfriend and they’re not really good friends, but all the same, twenty-nine starts off with a bang. Yes, cliché, I know.

It’s not my fault (yes, it is). The “boyfriend,” Steve, a.k.a. the boy I’ve gone on three dates with, a.k.a. the twenty-two-year-old DJ who also works in the footwear department at a Dick’s Sporting Goods and lives at home with his mother, is the one who invited me to go to the Eagle one night. For those not aware, the Eagle is a bear bar: a watering hole whose clientele mostly consists of overweight or bearded or overweight and bearded gay men.

Steve, the DJ, is a bear. He’s 6’3, 280 pounds, and has a burly beard. Steve is not a subtle person. He is loud, awkward, hilarious, and a total sweetheart. Of course, then, I would end up in bed with his friend the night before my birthday. This is not something I normally do. I am a kind, smart, and compassionate person. So when I meet Steve’s friends at the Eagle on that Thursday night, I am not prepared for Derek. Derek has tattoos, curly hair, and a motorcycle. Derek is a bad boy. Indeed, from the moment we meet, he chain-smokes and gives me shit about how Steve and I had met (Grindr, the super classy hookup app).

Throughout the night, Derek and I continue to lock eyes from across our little group. Now, this is not something that ever happens to me. I don’t just meet guys and have that instant connection. Grindr, Tinder, OKCupid, etc. have facilitated all of my previous dates. This is different, exciting, and new. However, I am there with Steve. When we leave the bar that night, I put Derek out of my mind, thinking of him as nothing more than a brief flirtation.

Cut to 10:10am the next morning. My phone chirps; I look down. It’s a Facebook message from Derek! My heart skips a beat. Oh god, it’s the guy from last night. Play it cool. “Yo Dude.” “Hey man.” And so it begins. After some pleasantries and skirting the issue of the previous night’s flirtation, he asks me to join him for dinner. I hesitate, conflicted for Steve’s sake, but when Derek chooses a bar six blocks from my West Hollywood apartment, the decision is made.

Like every good casual dater knows, it’s always important to have an exit strategy. The guy could be weird, crazy, or violent. You never know. Luckily, I have the perfect excuse: for months, I’d been planning a birthday camping trip with friends. “I can only meet for an hour. I’ve got tons to do before my camping trip.” Right. Five hours, seven beers, and no dinner later, it’s officially my birthday. Honestly, we have a fantastic time. We make lots of good conversation, flirt, dance to “Let’s Hear It for the Boy” from the Footloose soundtrack, and chat with a group of girls for a while. I am far too drunk to drive home, even just those six blocks, so we order an Uber.

We get to his house — which he owns! — around one o’clock in the morning. The differences between a twenty-two-year-old and a thirty-one-year-old are obvious. Derek is a man. Holy. Shit.

We sleep for about three hours because I have to meet my camping friends. Derek drops me off at my car and I make my way home in a complete daze. My ass sore and my head pounding, I arrive at home, park for the camping trip and think about dying. Instead, I grab my gear and head out the door.

The entire camping trip is a blur. I remember excitedly telling my friends about the previous night’s escapades, and sheepishly admit how sore my ass is. The rest of the trip is spent swimming in the ocean, drinking tons of beer, and grilling burgers. This is the perfect way to ring in a birthday.


Later, back in my apartment, however, I feel like crying. I suffer from depression, anxiety, and a slight case of obsessive-compulsive disorder. For the last five years, I’ve been on a variety of medications to balance my moods and my mind. After over a year of taking one specific medication, which resulted in a complete loss of my sex drive, I am now taking Zoloft, which seems to be working just fine.

My therapist and I are still trying to come up with the correct dosage for me, so every once in a while, my depression and anxiety get the best of me. Throw in a side of OCD so I can obsess about being depressed and anxious and it’s a regular party in my head.

I’m wallowing in self-pity. Neither of my roommates is home. There’s nothing worse than being alone when you’re depressed. OK, fine, there’s nothing worse than being depressed, period. When I’m lonely, I almost always need some sort of attention from a guy, so I look for someone to text. There’s Dylan from OKCupid, Michael from Tinder, John from Grindr, and Brian, also from Tinder. There’s also Steve the DJ, who I’m technically dating, and then there’s Derek, the birthday sex partner.

I text all of them.

I love to put myself in potentially awkward situations. Dylan is checking Instagram at home. Boring. Michael is driving from Arizona back to LA. Inconvenient. Steve, bless his heart, wants me to meet more of his friends next weekend. I let him down gently, telling him I’m not looking for anything serious at the moment (well, at least not with him). Steve does not like this response. He doesn’t want his heart broken. I don’t blame him. I’m not looking for what he wants, and he’s not getting what he needs from me, so we decide to pull the plug on our short-lived relationship. Goodbye, Steve, the twenty-two-year-old DJ that lives at home with his mother. Sorry I’m not sorry I fucked your friend the other night.

Derek asks about the camping trip. He also asks if I’ve told Steve about our scandalous night of lovemaking. I hesitate when he invites me over to watch a movie. I’m tired and sore from camping (and fucking), half-depressed, and anxious as hell. Plus, I’m not really in the mood to be my most charming self. I tell him I might be interested in movie night, but I need to hike Runyon Canyon first.

Runyon is just what I needed. The endorphins from hiking totally lift my spirits. I love how a ninety-minute hike can turn a whole day around. Guess who’s going to movie night…!

Derek is a total doll, and sexy too. He’s way into sports, which I find hilarious and weird. I get to his house around 8:00pm and see the place sober. It’s really nice: a cute ranch with a little yard and everything. I am impressed. The dude has his shit together. He continues his charm tour as we decide on a movie. He offers me a drink, popcorn, and an Otter Pop. We put on Noah, the Russell Crowe movie, and snuggle on the couch. Aside from the movie being fairly ridiculous, we have a good time. We make out, but keep our clothes on. Sometimes I can be a gentleman, especially if it’s with someone I like. This won’t end well.

It’s one thing to suffer from bouts of anxiety, but to then obsess over that anxiety too? The worst. My Zoloft dosage isn’t quite right yet — I still feel complete and utter despair at random points throughout the day. This shit is serious. I understand why people find themselves contemplating suicide. Luckily, I’ve never reached that point, but I can see how easy it could be. The OCD kicks in big time while talking to Derek. If I don’t get a response from him within two minutes, I automatically think I’ve said or done something wrong and that he is no longer interested in me. I recognize that this is completely illogical, but I still think that way. I can’t help it. It’s frustrating to no end.

I start to obsess over Derek. I drive by his house after work. I check his Instagram to see where he’s going to be at night. He meets me for drinks one night; we end up back at his house to fuck. The next morning, he all but kicks me out of bed. He’s got plans for the day. We try going out to dinner. It’s a bad date. Whatever chemistry we have doesn’t extend beyond the bedroom. We fuck again. He’s too busy during the day to text. I check his Facebook page. He doesn’t return my calls.

Finally, it’s Thanksgiving — two months after the initial birthday sex. Knowing he’s just had shoulder surgery a few days earlier, I decide it’ll be sweet to drop by his house with an apple pie and a carton of vanilla ice cream. He’s surprised to see me. I give him a kiss, but something feels off. I stay and chat for a few minutes, but I can sense that he doesn’t want me to stay. I leave; I’ve got plans for Thanksgiving dinner.

Three hours later, I receive a text: “Thanks so much for the apple pie. You’re a really sweet guy.” And then the kicker: “I don’t really see this going anywhere other than a friendship.” Ouch. Yet another failed relationship. Though at this point, why should I be surprised? I’ve officially been dating for fourteen years now, and not one relationship has ended well. Clearly, I’ve made some bad decisions along the way.

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