Trapped in the middle on October 12, 1998…

Dear Breakup Girl,

I have been dating this girl for about a month now. She is a really pretty, nice, smart, and sweet girl. But there is a problem. I think that I might have started dating her for the wrong reasons. There is this guy that keeps bugging her and tells her that he loves her and all this junk, and she doesn’t like it. The more I think about it, the more I feel that I started dating her to protect her from this guy.

But, that’s not all. I’m the type of guy that my friends rely on to help them with their troubles. Especially being the middle man when my friends break up. You know, being the nice guy, trying to cheer them up. But this time something happened between me and the girl whom I was trying to cheer up. This is another big problem because the girl just broke up with one of my good friends.

I need some serious help.

— Flip

Dear Flip,

Whoops!
Here’s how to be a gal’s main — not Middle — man. Trust her to like you because you’re being who you are, not because you’re Helping. When the next one comes along (or, at least, when you reevaluate your current flame), assume she wants a boy, not a bodyguard (unless she’s Whitney Houston).

Love,
Breakup Girl

Apart of nothing from October 12, 1998…

Dear Breakup Girl,

I am 16 years old and recently my boyfriend moved quite far away. We were very much in love. When it came to the idea of breaking up, my boyfriend told me we weren’t really breaking up, we are “breaking apart.” Whatever that means. I’m really not sure. It will be a very long time before he comes back to visit and I don’t know if I should date ever. I still love him a lot and I know that he is the only guy I want to be with, but is it foolish to wait at such a young age. I know I should probably be discussing this with him but I’m not sure he understands either. Every thing is so confusing. I’d really like to know if I’m wasting my time and if I should even still call him my boyfriend. I hope “breaking apart” isn’t just a nicer term for breakup but I don’t understand the so-called difference. Do you think you could clear this up for me? I would really like to know where I stand.

— Isabella

Dear Isabella,

Never mind the difference between up and apart— I think the real keyword is away. As in “quite far.” I’m not saying you shouldn’t try and stay “together,” but it will be hard — especially if you don’t talk to each other honestly about what your intentions and expectations are. This situation is totally confusing! Your brain knows it’s foolish to wait, but your heart’s like, “….Waaaaaaaiiit!” So yeah, give yourselves a real talk — how does each of you feel about “seeing other people?” etc. — and give yourselves some time to get used to being apart, whatever your status. Even if the new key word turns out to be over, you’ll be down, but — I promise — you’ll get through. (How can I be so sure? Remember: he’s away, not in all of your classes. Waaaay easier to move on.)

Love,
Breakup Girl

Sex with an Ex on October 12, 1998…

Dear Breakup Girl,

Let’s-call-him-Jack and I have been broken up for nearly six months after dating for nearly 3 years. We tried the friend thing for a while and it worked out quite nicely except I foolishly took every nicety as a sign that he wanted me back. But now I know that just isn’t going to happen and I’m fine with it, although I still think about him every day, multiple times a day. However, I sort of have the hots for someone else AND am enjoying being single. My question is, Jack and I started sleeping together again in late June (we broke up in March) and have done it 5 times since then. We are always drunk when this happens but the sex is INCREDIBLE. The first few times he would not kiss me and we would not cuddle afterwards, just roll over and go to sleep. However, I mentioned the no-kissing policy made me feel like a prostitute so the last two times he has kissed me and held me BEFORE and AFTER we did it. The problem is, I know it is stupid to have sex with an ex, but what if it is REALLY good and you aren’t nursing false hopes of reconciliation? Also, what’s up with the kissing thing? Please help!!!

— Confused yet Satisfied

Dear Confused yet Satisfied,

I’ve said it before, I’ll say it again: of course the sex rocks your world. There’s no aphrodisiac like a breakup. As in, “You look great without … commitment.”

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Opening up on October 12, 1998…

Dear Breakup Girl,

I’m a 18-year-old college student who is really shy. There’s this girl in one of my classes who I’m attracted to. I think she’s attracted to me, also. We played the little game where you look at someone and when you get caught by that person, you look away. I haven’t had a g/f in a long time. I also haven’t been really lucky for some reason with girls. We say hi to each other when we meet. But we never really talk. So I would like to know how should I go about to start talking to her? I don’t want to open myself to her so much. And I don’t want to get my hopes high either. I would really like to get to know her, but really don’t know where to start. If you have any advice, I would really appreciate it. Thanx for your time.

— Edward

Dear Edward,

Talking to someone is not the same as opening up to someone. Some people talk to each other for years without ever opening up. You start talking, you open up, little by little, as you’re ready. So take a hint from Chris (below) and pipe up.

Love,
Breakup Girl