The Worst Valentine’s Day Ever

I have intimacy issues because of my strong Protestant upbringing, and abandonment issues because of my parents’ broken, loveless marriage. It’s a lot funnier than it sounds.

For one, I’m not saying that I’ll call a woman I’m dating every five minutes to make sure she hasn’t betrayed me. I am saying that sometimes I wake up hugging a pillow. Nor am I saying that if you touch me I’ll scream, but I am saying that a couple weeks ago I saw a pretty girl I’d been flirting with sitting alone at a bar with an empty glass, and I said, “Trying to get the bartender’s attention?” and she said, “Yeah, but it’s like I’m invisible,” and I said, “They’re really busy back there. Good luck!” and walked away.

Hey, you’re out of underwear too! Excuse me; I have to go do laundry.

If it makes any difference, I’ve been trying to overcome these weaknesses. Four years ago I was so closed-off that when a girl on my lap whispered, “I’m not wearing a bra” and “You have a boner,” my responses were “That’s nice” and “Sorry.” That wouldn’t happen today. Plus, I keep in touch with friends who live out of town now rather than assuming they’ve moved on like Mom did.

Just stringing together a bunch of stories about my sexual inadequacies would be over-sharing, even by my standards, not to mention disjointed and amateurish. Instead, here’s a story about how both of these seemingly opposite currents from my childhood came roaring up at the same time and I ended up alone on an hour-long rage walk through Boston winter at 3 am.

Check out my band Insecurity Currents. Or don’t.

Valentine’s Day 2010 was supposed to be big for me. I had just started seeing the results of my plan to transform from “sweaty and unfuckable” to “sweaty and unfuckable but not quite as overweight,” plus I was freshly returned from a semester abroad in the Netherlands, with all its attendant newfound worldliness. Every year up to then I spent at home trying to determine if masturbating would be too sad, but this year was different. This year, there was Allison.*

If you have to ask, the answer’s yes.

I met Allison the previous spring and didn’t think much about her until one night, when we talked for hours after an after-after-party and both decided to stay up and catch the sunrise. Being exhausted and having no romantic angle in mind helped me to avoid my typical intimacy-terror, so to my surprise we hit it off.

Of course, I was too insecure and uncommunicative to capitalize, so nothing happened. Then there was some (almost certainly imagined) will-they-won’t-they tension, and then we didn’t see each other for eight months.

Worth the wait!

Shortly after my return to Boston, she invited our mutual friend Carlos over. Her tone when Los put me on speakerphone, plus her politeness when we went to her place, plus the fact that Los and I had the same emotional screws loose and he amplified my already out-of-proportion expectations, led me to believe that Allison and I were weeks away from eloping in Vegas.

So I super-vaguely asked her if she wanted to do something, and like I’d be there, sometime maybe next week, whenever. And she said yes!

Usually only the McRib gets me this excited.

Well, not really. She said, “I was going to throw a Valentine’s Day party for my single friends at my place, but it looks like most of them can’t come. You’re welcome to stop by if you want.” Most of you would hear, “I announced my plans to people in our mutual social circle and so if I don’t mention them and you find out later I’ll look mean, so I’ll let you down easy by inviting you to something a sane person wouldn’t go to and hope you get the message.” But I heard: “I’m gonna be all alone on Valentine’s Day. Won’t you please comfort me with your genitals?”

With pleasure, citizen.

As you might expect from Mr. Mommy Left So I Have To Hang Onto You Forever Because You Smiled At Me Once, I showed up to her place on the fourteenth. Turned out that by “most of her friends,” she meant “everyone but you and one loud guy who’s been drinking since noon.” Uh oh.

“Hey man, I’ve seen you around somewhere. What’s your name?” said the guy in Allison’s living room gesturing freely with a handle of rum. “Yeah. Peter. Tim, right?” said the guy in Allison’s living room who handles confrontation with panic attacks and high pitched laughter. We shook hands. His arms were as hairy as a Greek sasquatch’s, his grip as crushing as my feelings of inadequacy.

I could barely pee in a public bathroom if there was another guy in that time zone. Now I had to make my first date moves while sharing a couch with Alpha T. Budweiser.

“You called?”

It did not go fucking swimmingly. Huge problem number one: Tim would not stop talking. What, was I supposed to win her over with my looks and charm? My signature pickup strategy back then (now) is to yammer on until she breaks down and laughs at something I say (me). This means I had to settle for eye contact, smiles, and body language, all of which I over-thought until I reached a Creepometer of Ginger Little Person.

In an effort to solve problem one, I decided to rely on liquid courage for a confidence boost. Huge problem number two: apparently, when I get drunk on disastrous non-dates, I gain zero confidence and triple the Leering and Handsy quotients on the Creepometer until I shoot all the way up to Clown Doll on a Rusted Swing at Midnight.

Never doubt Google Images.

This did nothing to help huge problem number three: I wasn’t yet aware that I’d just developed lactose intolerance, and judging by the sounds my insides were making I ate thirty pizzas that day.

Let’s review. I’m drunk on a couch next to a girl I have a crush on, who’s next to a large drunk man. I’m trying to keep my head up enough to watch Allison’s Star Trek DVD, trying harder not to literally shit myself, and trying even harder still to somehow translate this into me getting laid later.

“Dijou know you’re preddy? Nobody ever told you that probally an they should. Wanmy beers?”

Still, that ain’t shit compared to what happened next. Since Allison lived a ways away from either of us and Boston’s subway closes at 12:30, she offered to let us stay in her living room. Tim took advantage of this by getting blackout drunk and, huge problem number four, having a nervous breakdown in a heap on her floor.

I got to know Tim very, very well that night. I know his most deeply buried anxieties, I know what he misses about his father, I know where he got stabbed. That’s a lot of unwanted intimacy for somebody who’s hugged his best friend twice. Best of all, I got to watch Allison soothe his troubled mind with an expert touch while I sat on the couch and stared at them like a distant cousin at a funeral.

I miss Craig. Greg. There are sandwiches, right?

After about an hour of this, Tim calmed down enough to get to sleep. Finally, I thought, the world’s worst third wheel has been tamed. I settled into Allison’s couch while Tim used her bathroom. Then, HUGEST PROBLEM: SEX NOISES.

Fuck!!! I opened one eye. Yep. Tim was gone. God fucking dammit. I laid down some medieval curses on my night, like fuck tonight and tonight’s next seven hundred generations. I’m the world’s worst third wheel! I showed up here barely-invited, drank her liquor, and sat here like a dick until the train closed. I’m that guy forever.

They were getting louder. I shot up and gathered my stuff, sure to make as much noise as possible because what the hell guys, and stormed out. Then, as I turned to close the front door behind me, what should I see but Tim sitting at the kitchen table, head in his hands, Allison rubbing his shoulders. I froze, but it was too late; the door slammed. Loudly.

How romantic.

Oh, right. Allison’s roommate’s boyfriend showed up earlier, and I just implied that she’s the kind of person who’d screw Tim with me still in the other room. Not only did I manage to blow whatever chance I may or may not have had with Allison, I blew even the chance to sleep on her couch. So a-walkin’ I did go—three miles, across the Charles River, in zero degree wind, feeling like an asshole, alone at 3 am the day after the only Valentine’s Day I’d ever had hope for.

There was no second date.

Dodged a bullet!

*This story is way too personal, so for the first time I’m changing the names. The sort-of-romantic interest and the drunk guy, who are both now my friends, have had their names replaced by a different sort-of-romantic interest and drunk guy (who are also my friends). Hi guys!

4 thoughts on “The Worst Valentine’s Day Ever

  1. Laurel says:

    This is actually hysterical in a “I shouldn’t laugh because I’ve been there and I’m your friend” way. Here’s to a better one in the years coming?

  2. The Skeptical Magician says:

    That was hilarious!!!! Thank you for allowing me to laugh at your misfortune and awkwardness.

  3. John Public says:

    I thought that was a cool story. I’m kinda surprised people share stories like this though; like friends or relatives don’t somehow stumble upon your blog?
    I don’t even know you personally in any way and I found your website (at least if you’re the person I think you are).

    Anyway, why was it that the relationship would be horribly lost? While it certainly screwed with your chances, one could always try to explain things (preferably not by lying, but sometimes it might help if it’s something really minor).
    How’s “Tim’s” and “Allison’s” relationship now? and how’s your relationship with them?

  4. Anonymous says:

    Bro this made my day.

    You are the first WordPress blogger ill be following.

    Nice one.

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