How to Completely Half-Ass an Important Conversation


As many of you might have guessed from my last post, I had recently been contemplating making things official with the guy I’ve been dating for the past month or so. (Woah, exciting!) As a bit of a recap, over the course of the past five months I’ve gone from being depressingly single after being abandoned without explanation to going on three dates with three different guys in a single weekend to becoming happily monogamous with someone I really like. That seems like a natural-ish progression of events, I suppose.

Anyway, that’s not really my point here. My point is that for the past week or so, I’d been thinking about the inevitable conversation that I would have to initiate in order to state my intentions that I had no desire to see anyone else and how I hoped that he didn’t either.

That’s kind of a difficult conversation, especially if:

  • You’re the type of person who gets nervous or anxious about simple things, such as scheduling a doctor’s appointment over the phone or not submitting your taxes properly.
  • You’ve already talked about the elephant in the room: why you’re both online dating, the craziest online date you’ve been on, how many relationships you’ve been in, etc.
  • It appears from every angle (how much time you spend together or how “dates” have smoothly transitioned into “hanging out and staying over”)  that no conversation is needed, despite the presence of social norms which allow you to see other people until you’ve strictly made it official.

I think I go against the grain in that once I go on a few dates with a guy I like, I don’t actively try to see or meet other people, in the hopes that dates will transition into a relationship. If I wanted to pursue other options, I would — but I never do.

I thought about ways I could begin the conversation (“So, I was thinking about deleting my OkCupid account…” or “I’ve been assuming we’re exclusive, I hope I’m right…?”), mulled the details of the situation over and over (and over) again, picked friends’ brains about what I should do, agonized and made myself nervous, and last night finally decided to man up and do it. Continue reading

A Brief List of Some Awkward Things I Did in 2011

Before entering a new, fresh year with a clean slate, it’s always good to reflect on the past year. Since I’m an awkward person, here are the awkward things (well, the ones I can remember) that I did with such poise and grace in 2011.

  1. While having a discussion in the office about something completely unrelated to Mean Girls, a bunch of us started talking about Mean Girls and then I brought up this gem. Everyone looked at me, laughed awkwardly, and we all dispersed.
  2. Convinced this guy I was sort of seeing* to stick with his plan of taking me to meet his friends after he had a complex emotional breakdown about how he “didn’t want a girlfriend,” mostly stemming from concerns about not being well-endowed (I am being completely serious). When we got there, his friends picked up on the awkward tension almost immediately and began feeding me wine, which helped on my end but it was still easily one of the most awkward situations I have ever gotten myself into. Willingly.
  3. Tweeted a countdown to the New Year while imbibing red wine at my mom’s friend’s house, and posted it at exactly 12:00 on January 1. This year, I’m going to kiss a (hopefully) handsome stranger at midnight and hope that things don’t turn out like they did with that guy from #2.
  4.  Mailed a handmade card to another guy I was sort of seeing (we actually went on dates, so it’s a little better than #2) who had stopped talking to me without an explanation. I think I thought he would magically start talking to me again, but this didn’t happen. Um. Yeah.
  5. Applied to a job posting on Mediabistro for a position I can’t actually remember the name of. They told me to write a funny cover letter, so I did. They didn’t hire me. Translation: I’m not as funny as I think I am.
  6. Retweeted a lot of @omgidothistoo‘s tweets because I was like, “Oh my god, I do this too!” (Aka: the point.)
  7. Went to a neighborhood association event across the street from my apartment with a friend who doesn’t live in my neighborhood, drank a beer without socializing with anyone but her, attempted to make eyes at some potentially cute guys across the room (it was pretty dark so I couldn’t really tell), and left after 30 minutes. Later, I complained about not knowing anyone besides the people I graduated with who stayed in town and the growing number of guys I don’t talk to anymore after dating them briefly.
  8. Traded the cashier at Panera two dollar bills for quarters while ordering lunch so I could do laundry. She was hesitant to open the register, because I paid with a card, but I think my sad puppy eyes about not having any clean clothes convinced her to make the trade.
  9. Snuck up behind my friend’s ex-boyfriend at a formal event where I already stuck out because I hardly knew anyone and covered his eyes to make him guess who I was. The result: he turned around, gave me a weird look, told me to enjoy my night, and walked away, resuming conversation with three other girls. (Yes, I also interrupted the conversation he was having. Oops.)
  10. Just went through all of my tweets from this past year to figure out all of the awkward things I did in order to complete this blog post. I feel like I’m coming up short, somehow. Happy almost new year, everyone!

*This is a loose definition, as our sad summer fling consisted of: us making out in a sketchy club in January, accidentally running into each other again in June at the same club, him booty-calling me two weekends in a row, spending 4th of July together, and him actually calling me 3 other times while he spent a month at home 2 hours away.

Should I text him? (No, probably not.)

Credit: Becca Clason

I hate texting men. Why? Men either:

a) Suck at texting. If you send them a text at 3pm on a Saturday to make plans (a perfectly reasonable time — they should be awake by then) they don’t reply until 8pm, at which point you’ve resigned to staying in with a bottle of wine, a movie, and possibly a girlfriend or two to over-analyze why he sucks at texting you back.

b) Miraculously don’t suck at texting. If only I could meet a man who is attached to his phone as much as I am…

c) Annoy the shit out of you with their text messages, no matter how frequent or infrequent. (See: Texts from Bennett, although not quite as ridden with grammatical, spelling, and cultural errors.)

Regardless: I usually go out with guys who seriously don’t know how to operate a phone, so I’m normally the one who ends up initiating the text conversation. Thus, the helpfulness of this well-designed flowchart. I have a few rules to keep my texting habits in check, mostly so I don’t freak the guy out — but also to keep myself sane.

  1. If you want to guarantee a response, ask a question at the end of the text. That’s the last thing he’ll see, and if he’s not a total jerkface, he’ll feel somewhat obligated to respond. Level of crazy (1-5): 1. New questions are what keep the conversation flowing, unless you’re asking “where are you?” and “what are you doing?” and “are you sure you can’t hang out tonight? :(“
  2. Two texts in a row are acceptable, but only when you’re either: a) clarifying information that may have been misunderstood in a previous text, b) trying to make plans, or c) texting him again after a 24-hour period has passed. Three texts in a row, sent in a 24-hour period without any response from him, are absolutely unacceptable. Level of crazy: 3. I’ve had issues with being clingy in the past, so this rule might be a little strict.
  3. If he’s taking awhile to respond in between texts, do the same — he’s making you wait, so he can wait too. Level of crazy: 1. It’s not crazy. It’s called not being an eager beaver.

So, I have my rules. Thankfully, it means I’ve never been this girl. Ladies, I want to hear from you: do you make yourself follow any rules when texting a new guy or does anything go?