What is he thinking?!

Got a little question for Tuffy Luv? She’s got a little answer for you! Email questions to TuffyLuv@collegecandy.com for a chance to be featured in the Tuffster’s column.

Dear Tuffy Luv,

So, I have a cozy, late-night nookie friend.

We’re not overly compatible in the sobering light of day, and we’re both unusually insecure, so the unspoken rule seems to be every couple of weeks or more. Emails are sporadic and sweet, for reasons that any of you who’ve ever binged on ice cream before or heard the chorus of the Elliott Smith song “Ballad of Big Nothing” will know.

I disappeared this summer, so falling back into a routine feels like navigating the bumpy straits of first acquaintance all over again. We’ve only seen each other three times this fall, but a few weeks ago, maybe moved by birthday drinks or the card that I sent him, he sent me an email telling me to barge in whenever I felt like it.

Yesterday I favorited three of his photos on flickr after he sent me a link to them (I don’t do much favoriting or flickring), did some back-and-forthing on gmail (felt reminiscent of my lame puppy crush days), and took off on my bike for his house after he invited me to come over and continue the conversation in person. I didn’t send him any kind of confirmation message, figuring it would be a nicer surprise just to show up.

All his lights were on, but he wasn’t there.

Asleep? Passed out? Gone for a walk? I called and left a short, gloomy message lacking in the appropriate nonchalance. Then I went home.

Now I just feel kind of embarrassed. Should I be?

Yours,
Rachel

Dear Rachel,

Tuffy can’t help but be moved by the eloquence and odd self-referentialism of your letter. So, let’s do this.

Quickly, to get it out of the way: No, I don’t think you should be embarrassed. He invited you over. You showed up (albeit, unannounced). He wasn’t prepared. (Perhaps, as you say, he was asleep? Or maybe he was just nakey or something and was too flustered to get it together to come greet you at the door.) I think this was just a minor mis-communication. Sometimes surprises don’t work out that well. No big deal.

I also don’t think you should be embarrassed by the overly-enthusiastic message you say you left. He’s probably, in fact, already called you back at the time of this posting. If not, perhaps he was just too shy to return it.

Which brings me to what I actually want to say about your letter. I’m mostly worried about the idea that the two of you are “both unusually insecure.” Because, you know, that’s actually exactly what’s holding you back.

For those of you who do not have access to either the CollegeCandy Tuffy Luv email or Rachel’s computer, the subject of the email was: “overthinking my friendship with benefits?” To that end, girl, yes, you are. At least the way things are going now. You hook up every couple of weeks and that’s that.

But!

You seem to actually like each other (birthday cards, sweet emails, Flickr favoriting or whatever you crazy kids are doing these days), so I don’t see why you aren’t dating. You both seem to be clumsily attempting to move into that space, but both of your insecurities are getting in the way. It’s like college-age Woody Allens trying to date each other. And you seem like such a cool girl, so I hate to see that go down.

Unfortch, there’s no magic potion for getting over being insecure. Except, you know, getting older and ceasing to worry that people are judging you. Because usually they’re too busy judging themselves. And if they are judging you, chances are they’re too miserable to really matter.

So: cut that shiz out!!! Get over yourself and call him up and propose a hangout. If it doesn’t work out, whatever – it’s not like you’ll be losing some great friendship. But if it does work out, well, wouldn’t that be nice?

Best, Rach!

Hearts & Skulls,

Tuffy Luv