Ask Kayy

Dear Kayy,

My problem is something that in my opinion shouldn’t be a problem. My best friend used to date this guy in high school, but it was never a serious relationship. It only lasted a few months, and even before she broke it off, she was constantly talking badly about him and wondering out loud why she was with him in the first place. After they broke up, they went back to being friends, which she was happy about since she never really had romantic feelings for him anyway.

This guy, let’s say his name is “John,” and I have been talking a lot lately and have been flirting, and we definitely like each other (we’ve admitted it several times). When I told my best friend about this, thinking she’d consider it either great or at least amusing, she got totally pissed off!

I told her I was confused, because she said she never liked him. She told me she saw this coming for years and accused me of plotting to get with him behind her back. I was totally caught off guard and offended and haven’t spoken to her in the past few weeks. I want to make things right but still really want to pursue things with “John”!


Unintentional Boy Stealer

Dear Unintentional Boy Stealer,

Quite the sticky situation you’ve gotten yourself into here. Do you stay loyal to her and lonely, or go for it with him and get into a catfight? Fortunately, there are several ways you can go about this without bloodshed.

Most importantly, you have to figure out how you feel about this guy. Have you always had feelings for him like your friend accused? Do you only want him because he’s a forbidden ex? Do you want to have his children, or just have a fling with a hottie? I’m asking these questions because the answers will determine your course of action.

If you just want a string of casual hookups, or know you only want to do it to stick it to your friend, stop reading here and back away from the boy. I’m sure you think he’s a great guy, but aren’t you better off resisting and avoiding problems if it’s not serious? (Unless you’re the self-sabotaging type who constantly craves drama.)

If you have more than tiny doubts about whether this guy is worth it, can it. But if you are as curious as you claim to be, and are really interested in pursuing things, you’ve got a trickier maneuver ahead of you.

Not only do you have to be honest with yourself, but you need to be honest with him. Unless you’re a mind reader, you can’t be sure what he wants from you. Don’t project your romantic feelings on him and assume he wants something special. Flat out ask him! And pay attention to how he answers (i.e. try to detect if he’s bullshitting you).

If you want more than a hookup and he doesn’t, you probably shouldn’t pursue it. Don’t start hooking up, hoping you can change him into a serial monogamist. If he doesn’t want what you want, fuh-getta ’bout it – your girl is more important. (There are plenty of fish in the sea . Go fish!) My readers know I’m never one turn down a steamy hookup, but this is obviously more complicated.

On a semi-side note . whether it takes prodding him or asking around, you definitely have to find out how the breakup with your friend affected him. She may have been totally OK with it (since she initiated it), but he may have been left heartbroken, depressed or, worst of all, vengeful. Find this out, because unless he’s totally apathetic about your BFF, we’ve just added another very ugly layer to the drama cake.

If he harbors any resentment toward her, you have no choice but to question his motives with you. It may sound crazy or even neurotic, but trust me, it matters.

If he’s still heartbroken, he may be getting with you to either get over or get closer to her. Or, if he has any festering anger, there’s a good chance he’s talking to you to make her jealous, piss her off, hurt her or prove something. I’m not saying these things are definite, but they are definite possibilities. If he’s in love, or in hate, with your best friend, you will be the one to get burned.

If you’re still craving advice, that means you know you want to try things and you’re pretty sure he does too (I hope).

In that case, make sure you also talk to him about the risks you’re both running, since you are both friends with his ex. Make an action plan, which should probably consist of you approaching her (with no claws and no bad intentions).

You need to talk to her again, whether you decide to move along with this guy or not. Going back to the getting burned part, I was in the exact same position about three years ago. Fortunately for me, my best friend wasn’t pissed and even supported the idea.

Unfortunately, the guy was definitely not over her, and regardless of the poetry he wrote me and the sweet kisses he gave me, he was just using me.

I got burned, very badly, but at least I had my best friend by my side. In some weird ways, it even brought us together (at least we could criticize his sloppy kissing and bad hair together).

But your friend doesn’t seem to be taking as well to the idea. Talk to her and find out why. Sharing an ex with a best friend is harder than sharing lip gloss.

If you’re convinced that you and Mr. Dreamy deserve to be together, tell her that! Explain your feelings; even if it makes her mad at first, she’ll probably begin to see your side. Point out that you purposely did not act on your lust before you talked to her, because you are concerned about her feelings.

If she doesn’t lighten up, consider where she’s coming from and weigh your options. Don’t let her make you back down too easily, but take her feelings into account before you decide what to do.

Worst comes to worst, cool your jets, tell “John” to take a cold shower and let your friend think about everything you’ve said and get back to you.

Tell him you need to wait, and if he disappears in the meantime, he just made your decision a lot easier. But if he sticks around, keep hoping she’ll chill out and tell you to go for it, but proceed with caution.

That’s all I’ve got!