Miss Information: Should I tell him that size was the dealbreaker?

Pin it


Have a question? Email Letters may be edited for length, content and clarity.

Dear Miss Information,

Help me out here: how do you tell a guy that his penis is too small without hurting his feelings or coming off like an uncaring bitch? We’ve hooked up twice now and both times it was unsatisfying. He’s fine otherwise, but this is a dealbreaker. I don’t need a guy who’s huge; there is such a thing as too big. I’ve been blowing off his emails. I feel like I have to explain why I don’t want to go out again. — Baby-Carrot Discontent

Dear Baby-Carrot Discontent,

Are you high? If dick size is a genuine dealbreaker, what on earth would be gained by telling this man he has a small penis? Bad breath you can fix with a mint. I’m sure if there were a way to cross “swing by Target, pick up Swiffer refills and extra-large penis” off his To-Do list, he would have done so already.

I sense some anger here, either with him specifically or with dating in general. Genitals are an easy target for frustration. They’re personal and vulnerable, great for when you want to say something really cutting and mean. I’ve wanted for years to tell this guy I dated that he had freakish, oversized balls. That would just be cruel though. I broke up with him because he was an arrogant tool, not because of his nuts.

If this strikes a chord, write him an email that never leaves your inbox. Go out for drinks with a couple of friends and draw unflattering penis pictures on cocktail napkins. It’s immature, no doubt, but a better way to vent those feelings.

The only way the small-penis talk will be helpful is if you’re really into this guy and want to see if the sex will get better. That doesn’t sound like you, though. You describe him as “fine,” a milquetoast description if I ever saw one. Fine is for patio umbrellas and USA Today editorials, not someone you really dig. If that’s the case, keep your mouth shut and deliver a generic, “Sorry, I’m not feeling it.” That’ll get the job done without making him feel like crap about his body.

Dear Miss Information,

My live-in boyfriend of nearly two years is moving out of state at the end of the month for a job opportunity. I’ve decided to stay. It’s been a mutual and somewhat amiable breakup. How soon would it be socially acceptable to sleep with someone within our circle of friends? I feel like I should go through a period of mourning, but this separation has been months in the making, so I’m ready for it to happen. — Just Asking

Dear Just Asking,

Your soon-to-be ex-boyfriend has beaten the odds. A cross-country job offer during a dreary economy and a friendly dissolution with his live-in girlfriend? He’s probably waiting for that 300-pound anvil to fall on his head, and it just so happens you’re the one about to drop it. It’s heavy and shiny and has the words “SHE’S FUCKING WHO?!” stamped on the bottom. Before you crush him, ask yourself these questions:

• Who’s better friends with the person you want to sleep with?

• Who’s feeling worse about the breakup?

• Who would be more hurt if either of you started seeing someone?

In order to date this friend, you have to be able honestly to answer “me” on all three counts. You need to check and then double-check that your object of desire isn’t “our friend” or “his friend” but “my friend.” Read through past emails, go over old phone bills, look through old pictures, and if you’re still having doubts, confirm with a third party.

You’ve got a strong case for friend-humping, what with a new job keeping your ex busy, the physical distance between you, and the slow-burn breakup. Then again, moving and a new job are two of the most stressful life events a person can go through. If he can find employment, surely you can find a partner outside your friend group.

That’s all you need right now, anyway: a good humpin’. You’re not ready for a relationship, and if you date someone you’ve known a long time, chances are strong it’ll morph into something more serious. Why not have fun with someone random, and save the friend for later? That way, there’s less risk of drama with your ex and you’ve got time to sort yourself out. If drama goes down and your ex freaks out, what kind of damage could be inflicted? Take your time and be cautious.

If you’re champing at the bit so bad that you’re reading this while staring at your crush’s Facebook, then at least wait until your guy is out of the house before making a move. Then wait a minimum of thirty to sixty days after that.

Readers, what do you think of that time frame? Too long? Too short? Just right? Are friend circle booty calls all right if the ex is in another town, or will they always be a faux pas?