Ask Kayy

Dear Kayy,

I was dating a guy over the summer and things went really well. The sex was especially amazing. Unfortunately, when the summer ended, we did too – really, really badly. Trust me, it was all his fault. Just recently he made an attempt to apologize to me. He took complete responsibility and told me he was ashamed of the way he acted and really upset about the way things ended (pretty much every girl’s post-breakup fantasy).

We hadn’t spoken since the end of August so it really came out of nowhere. Neither one of us is seeing anyone, and I have a feeling I know where this is headed. All of my friends are telling me to forget about him, but I’d be lying if I said I wasn’t interested. He lives in Hoboken, so the chances of this actually coming to fruition are slim to none. Please help!

Ho for Hoboken

Dear Ho for Hoboken,

It’s the classic “I realized I was wrong five months later when I was lonely watching Project Runway by myself” routine. Ahh, I know it well. For some reason, it seems there is something encoded on the Y chromosome that makes it take a little longer to realize guilt. Now, I’m not picking on men, but this certainly has been my experience.

For me, when I do something wrong, I instantly feel bad about it. If I genuinely hurt someone, whether it’s a friend, date or family member, especially if it was completely unwarranted, I take a little cool-off time and then apologize. That cooling period can last as little as a few minutes as my guilt eats away at me.

Sometimes I feel a guy’s “cooling period” is more like an ice age. I’ve gotten pokes three weeks later, sad, drunken text messages after a month, and paragraph e-mails almost a year later expressing anguish and regret. When it gets to that point, I can’t help but get suspicious. If you told me you were going to call one night and “forgot” to for a week, then why are you calling me now to apologize? If you messed with my head and hurt me four months ago, why the plea for forgiveness on this random Saturday afternoon?

Any excuse can work for why they didn’t call earlier: I know you’re sensitive and I didn’t want to upset you; it was too soon and I didn’t want to hurt you anymore; I made a mistake. (Translation: I didn’t want to deal with you crying and making me feel bad; I was scared you’d bitch me out; I have no idea why I did it ’cause I’m a jerk.)

I’m not saying it’s impossible for guilt to hit someone like a ton of bricks 180 days after the act was committed. It’s possible, I suppose. But I think what’s more at work is a person’s desire: desire for companionship, desire for love or desire for a kinky rendezvous.

They miss what they had, whatever it was, and although they might have felt bad for hurting you a while ago, it would have meant admitting too much wrong and feeling too much shame if they apologized. And so they put it off until they needed you (a.k.a. he or she wanted to get some).

It isn’t always as simple as a booty call. They might have real feelings but just got confused, scared or unsure about how to handle them. I’m not saying men lack any ability to communicate, but keep in mind that they don’t sit around for hours discussing their tiniest inklings and complicated emotions.

So maybe he does still have feelings for you, and maybe he’s finally figured them out for himself. Maybe he wants to marry you or maybe he just misses your “skills.” Who knows? The point is, you won’t know his intentions until you ask. Because trust me, he has intentions. I’ve been dumb enough to fall for that old flame who suddenly comes out of the woodwork (even though he’s lived in the same dorm for two years) asking you how things are. I’ve even fallen for the guy who apologizes for past wrong-doings, only to claim that “we should just be friends because of our great chemistry.” Ha!

My advice to you is to straight-up ask him what the deal is. He might be caught a little off guard, but to be honest, he kept you in the dark for six months and you deserve to hear it.

Even if he explains why he was a jerk half a year ago, that doesn’t explain how he feels now, what he wants now and where you fit into his crazy little mess of a head.

Those types of confrontations are tough, but I’m all about the cowardly instant message or e-mail.

Sure, the Internet has rendered half of our generation incapable of face-to-face personal conversation, but there are perks of typing rather than saying how you feel – unless you want to catch him off guard.

You obviously still have feelings for this guy. And whether those feelings reside above or below the waist, you deserve to figure them out. I know your friends are telling you “screw him,” and a less realistic Kayy would agree. But if he’s pursuing this and you’re curious enough about it to ask me for advice, I know you’re not going to just sit back and twiddle your thumbs while he pines for you.

However, there are obvious unresolved issues between you which need to be sorted out before any physical action can take place. You deserve to ask him questions.Where was he six months ago with his apology? Why did he act the way he did? Why has it taken him this long to do the right thing? I can’t answer these questions, but he might be able to try. If his answers aren’t satisfactory, he’s not worth it. If his apology isn’t genuine, don’t bother. I do believe people can change – but only if they want to.

Sniff out any possible bad intentions and make sure things aren’t too far beyond repair to start up again. Take your time, ’cause he sure as hell took his. My suggestion: invite him over for dinner with your best friends. If he’s up for that, surely he’s up for anything.

Peace & Love,


Kayy’s Spring Break Tips

*The Buddy System was invented for drunk college kids, not kindergartners.

*If that guy or girl from your psych class is starting to look really good, it could just be the Kahlua, sun or bad water talking.

*If you’re not going away, don’t overcook yourself with the fake-and-bake.

*If you’re under some sort of influence and on vacation away from your partner, for the love of God don’t let your eyes wander.

*If you’re going away with your partner, try to spend some quiet time away from each other.


*If you go against any of these things or commit any other Spring Break relationship faux pas, make sure to e-mail them to me ( so I can help!