Wednesday, February 24, 2010

How to Make Plans with a Cute Guy

You know that really cute guy, the one you always seem to hit it off with when you bump into him, and you think there could be something there, but you NEVER see each other?

It’s really frustrating to feel like you’ve finally found someone with when it seems like there’s nothing you can do about it.

But it helps if you treat this guy, not as a potential love interest, but as a girl that you’re dying to be friends with.

When your friend introduces you to her cool roommate form college who also secretly buys Chuck Klosterman’s latest book the day it comes out and then lies about it to all of her friends, you don’t try to make out with her.

You try to solicit her friendship, but you’re not desperate about it.

You need to do the same thing with this guy.

We’re not talking about the guy you make eyes with at the gym, or the guy that you see on the Metro in the morning but have no way of casually approaching.

But you have an in with the guy in your office who always makes you laugh or the friend of a friend that you sometimes see at bars.

To take things to the next level, you need to start seeing him more frequently. And for that, you need good plans and (in honor of vaginas finally being allowed on submarines) a Navigator.

First, you need to come up with legitimately fun plans. A new (and inexpensive) twist on drinking (think brewery tour) always attracts guys. Shows with bands you can dance to and still have fun even if you don’t know the music (e.g., Girl Talk, other mashup/electro groups that Baltimore discovered three years ago and now shun for being too mainstream) can be fun. If he seems more artsy/hipster, browse the City Paper for an uber underground film screening (cough The Room cough), or ask the nearest person wearing Converse and/or an ironic T-shirt for some recommendations.

Happy hours and bar hopping do not count as “cool” plans (unless the bars are totally new and underground and/or The Black Cat) and should be used as a last resort only. Museums, movies, and restaurants should be avoided at all costs (too date-ish, too awkward).

Then you need to find someone who can invite this guy for you—the Navigator. Ideally, the Navigator should have a boyfriend/be a guy/be otherwise unavailable so she can unabashedly invite this guy places and not look like she’s coming on to him. (Coworkers/friends who tangentially know this guy are ideal.)

The Navigator should make the plans and invite the guy along. He shows up, you’re there, fireworks ensue.

If you don’t have a Navigator, don’t worry. You can still invite this guy, but make it seem like you’re approaching him as a friend.

Invite him (and a group of girls AND guys) via Facebook message or e-mail so it doesn’t seem like you’re trying to make one-on-one plans.

Bring it up with him the next time you run into him. But stress the group element. Maybe throw in something about just moving to this city.

Above all, make sure you don’t come off as too eager/aggressive. As with everything in dating, you want to play hard to get.

But the guy’s so removed from your daily life that you don’t have the option of showing him your best game, sometimes you have to make the first move.

Just make sure it’s not obvious that you are, in fact, asking him out.


  1. What if you accidentally fall in love with the Navigator? Does the crush you originally planned the evening for become the Navigator designate?

  2. Great question. In that case, we suggest abandoning ship.

  3. Good point about not going to restaurants. So Awk, especially if you get something garlicky or that might make weird bulges in your stomach area.

  4. Well you could always just abandon ship, or see if you'll find them out to sea @