Dear Breakup Girl,

Best wishes from a core, real, die-hard Green Bay Packer Fan-esque fan.

I have had a few long term relationships (a few years each) but none for a while. I have never had a problem meeting women or even going on a date or two, but recently I haven’t been able to keep a long termer. I am in many ways too much of a friend for some women, but I am working on that. No one seems to set me up with anyone even though everyone claims they know someone I should go out with.

OK. Let’s get down to brass tacks. A platonic friend of mine (yet another who says I am too much of a friend, but I would make a good husband) took me out with a bunch of her friends just to hang out. I met a woman who was not only beautiful and friendly, but connected with me in a great, all beit non romantic way. Let’s call her Beth, because that’s her name. There was one small problem. She has a boyfriend whom she loves. So, she was clearly hands off, and I treated it as such. I told our mutual friend, Rhonda, that I have a huge crush on Beth. She thought it was cute and told Beth. I don’t mind. She’s flattered. I get a nice feeling that I made her feel beautiful and special, knowing DAMN WELL that nothing will come of this.

Well, Beth and her man are going through tough times. Real tough times. And Rhonda, our mutual friend, has always used my flattery as a way to cheer her up. “George thinks you are beautiful. He thinks this and that etc etc etc.” Rhonda, who dislikes Beth’s boyfriend, has been subtly pushing my case. In other words she wants Beth to leave her boyfriend and hook up with me. I of course said “I don’t want to be in the middle of anything.” But secretly I wanted her to. Now I know she has been suggesting that Beth take me a little more seriously while her relationship with her man gets tense. And I am guiltily encouraging it.

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Dear Breakup Girl,

This is kind of a biggie. I’m 23 years old. I still live at home with my ‘rents for financial reasons while I’m in graduate school, completing a degree in elementary education.

To get down to it, I haven’t had a date since I was 17. It’s not for want of trying. The times when I thought there was some mutual attraction, I would ask to see the person more socially, not necessarily on a date, but out. The few times that anyone has said yes over the past 6 years, it’s always turned out they were just being friendly, but were already involved with someone else. Plus, I suppose I’m not that good at reading “signals.” That takes experience, something I am greatly lacking.

Most of my friends are women, but I’ve never been able to move a friendship to a romance, nor have I really tried. I would consider it almost a betrayal of that friendship. I’m not into the bar scene, or clubs (I can’t dance). I’m not into religion, so meeting someone at church is out. I’ve tried personals, both online and off, with 0 success. For all that my best friends are women, none of them has ever set me up with someone.

Now it seems that all my friends are engaged, or involved in serious relationships (and as a consequence have little if any time to spend with me). My little sister, and my best friend’s little sister (same age, 3 years younger) are engaged. And every attractive, intelligent woman I meet seems to be married/engaged/or otherwise seriously involved. (I’m only meeting people at school and work. I hate going out by myself, and never meet anyone when I do.)

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Not getting the message on November 2, 1998…

Dear Breakup Girl,

There is this girl whom I’ve known for quite awhile and have liked romantically but still haven’t got anywhere with her other than just being friends. To combine problems she lives in another state but I do see her on a regular basis. She is moving in the near future and I have suggested that she to move closer to me. Anyway, the problem I have is her mixed signals. I read your advice on just asking and I have tried hard to get a response. I have backed her into a corner (so to speak) to get a response about whether she wants me romantically or wants me to just to be friends. She doesn’t say anything either way. I always give her an opportunity to back out and she never does. I have been the “nice guy” without trying too hard like you suggested. I have tested the waters by sending her flowers and gifts without too much of a response either way. I do really like this girl but it seems to be a one sided deal and would like a reponse either way. If she doesn’t like me I would like to hear it from her, instead of always being accommodating. What do you suggest I do to win her over (if that’s possible) ?

— Joe

BG’s answer after the jump!

Going no further on September 28, 1998…

Dear Breakup Girl,

One of my friends is totally in love with me but I have no feelings for him whatsoever. How can I tell him that I don’t like him without losing his friendship?

— Julianne

Dear Julianne,

The best you can do is this: break it to him sweetly but clearly. As in: “I have the hunch that you might like us to be more than friends. I think it’s important to tell you that I’m totally sorry, but I just don’t feel that way. Which also means that I love our relationship the way it is, and I hope that’ll still work for you too.” So if you do still want to be friends — and he can deal — then prove it … gently. Make an effort to keep everything the way it was — in terms of hanging out, talking, whatever you do together — but turned down one notch. This will let him know that you meant what you said, but it will also give him space to get over what you said. And wait a while before you get all Good Person and try to set him up with someone else. He may not be ready … and you may find yourself oddly jealous.

Love,
Breakup Girl

Striking out on September 28, 1998…

Dear Breakup Girl,

I am very close to one of my guy friends. He is one of those very friendly, touchy, huggy guys, who is wonderfully nice to everyone. Well, over the past months I have developed very strong feelings for him. I think about him all the time. A few days ago I couldn’t deal with it anymore so I told him I couldn’t see, talk, or be around him anymore because I had feelings for him. He was stunned. It’s been over a week and I haven’t seen him. The problem is that I REALLY miss him and now I just feel depressed. What should I do? I feel like I’ll always love him. It’s getting in the way of meeting new people. Now I’m wondering if I did the right thing.

— Jenna

Dear Jenna,

Oh, girlie, I don’t know if you did the “Right” thing, but I do know that you did what felt right at the time. And now, yes, of course you miss him. It’s almost like you’re going through a breakup with someone you didn’t even get to go out with! I guess what you’re gonna have to figure out is, which sucks less: not being WITHwith him, or not being with him at all? If he is indeed as generous with his heart as he is with his touchy huggy extremities — and indeed I bet he is — I’m sure he’d understand if you went back to him and told him that you don’t want things to stay this way. Which reminds me: you say he was stunned — are you quite sure he’s not interested? Or did you just freak out and split before you had a opportunity to see the gears turning? It’s worth looking into. But if not, well then yes: you do need to lick your wounds, mourn, and smart for a while, and then get back out and try and meet new folks, no matter what. That’s the right thing.

Love,
Breakup Girl

So you’ve got this great friend. You do everything together: shop, hang, talk, work out, talk about your lame love lives and NATO expansion. You know each other’s families; you take care of each other’s plants. You fend off friends’ suggestions that you should be a couple, saying, “No way, that would be too weird!”

But then, somehow, you realize, that what you really want to do … is the one thing you haven’t done together.

So you (a) freak out, and (b) make a list.

Valid points, all. And here are a few more, from Denver psychotherapist Carolyn Bushong: “Romances built on friendships can be deeper, stronger, and in some cases more ‘equal’ than others, especially when they start off mutually, with no one taking the role of pursuer or pursued. But, she says, love that didn’t start as lust also comes with a unique set of pitfalls and second thoughts. Couples may be troubled not only by the high stakes of gambling on a valuable friendship, but also by the feeling of having “settled,” she points out. “Especially when things aren’t going well, one person might wonder ‘What if I never was all that attracted to him? What if I was just comfortable…?'”

Ugh. So what are you going to do? Especially ’cause you can’t ask your, uh, friend for advice. That, of course, is where BG comes in:

• What to ask yourself.

“What flavor of friends are we?”

Are you longtime pals from, like, before you were old enough to date? (Pro: The “Mr./Ms. Right There All Along” thing. Con: You’ve already bathed together.) Or are you more recent friends who, for whatever reason (say, other boy./ girlfriends) have never had the opportunity to upgrade? There’s no one right way to proceed in either case; I’m just trying to give you ways to calibrate your feelings. In the latter scenario, for example, it’s possible that you’ve become friends because you’re attracted to one another — but you’ve been treading water for so long that no one dares take the plunge.

“Is the crush enhancing the friendship — or interfering with it?”

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Christmas wishing on December 14, 1998…

Dear Breakup Girl,

I met this really amazing guy three years ago, when I was dating another really amazing guy. AG#1 and I became fairly good friends, saw each other at school frequently and ended up on the one hour bus ride to and from school together fairly often. Sometime in the year that followed, I split with AG#2 (just our lived heading in different directions) at which point I went into dating overdrive. Being young and immature (18) but thinking I knew it all, there was a string of guys which I saw for a few weeks and then tossed aside, none of them were amazing. Meanwhile, AG#1 and I are spending more and more time together, going out for dinner, seeing movies, drinking at the bar after class together and having wonderfully stimulating (intellectually) discussions.

About a year and a half after our first meeting, we get quite inebriated and end up kissing on my front step and discussing the possibility of us getting together. I knew then that he felt more about me than I felt about him, but I went ahead anyway thinking, I should like him, he’s amazing! So what happens? The next day I flip out and tell him it’s not going to work, I can’t deal etc. etc. Being the AG that he is, he is totally cool about the whole thing. A few days later, he goes home for the summer, and the next fall, I leave to go away to school halfway across the country.

Well, it’s been a year and a half now since the whole kissing thing happened between us and we have still never talked about it. Things haven’t been quite the same between us since then either, and I feel totally terrible about my behaviour. Well, after an amazing dinner with him this summer, right before I again left to come back to school, I started to think about him in a different way, seriously this time. And since I’ve been back I sometimes miss him so much that it physically hurts me. The problem, there is no one else in my life right now, but there is someone in his. We talk on the phone and he doesn’t talk about her much, I get the feeling it’s not serious. And recently he totally hinted that he was still thinking about me as more that just his friend. I would like nothing more than to explore this possibility when I get home for Christmas, but am very unsure about whether or not he is on the same page as me. Plus, I want to be sure this time that I want a relationship with him, he’s so amazing that the thought of me hurting him again scares me. I more than anything don’t want to lose him as a friend. Any thoughts?

— Hoping to Change His Mind

BG doesn’t exactly break out the mistletoe after the jump

Crushed on September 7, 1998…

Dear Breakup Girl,

My dilemma sounds a lot like the movie “The Object of My Affection.” You know, the one where Jennifer Aniston falls in love with her gay best friend, played by Paul Rudd? Well anyways, my problem is that I have a huge crush on my guy friend. He’s wonderful, sweet, and shy. We can talk about anything with each other. The problem, as you probably guessed, is that he’s gay. Well, actually, he’s just very confused. Lately, he says he’s been experiencing an attraction to other men, and this really concerns and scares him. But I’m completely in love with him, and I don’t know what to do. He thinks there’s also a chance he’s bisexual. Should I be hoping for this? Is it possible to have a meaningful relationship with someone who’s attracted to both sexes?

— Paige

BG’s advice after the jump!

Out of order on September 7, 1998…

Dear Breakup Girl,

Here’s my situation. A few months ago, I moved into an apartment with a really good friend of mine, I’ll call her “Ann.” I liked living with her. We got along fine and we never fought about anything. I’ve always considered her one of my best friends, and although we flirted a bit it was nothing serious, just friend stuff. Anyway, a while back the two of us went out partying and had a bit too much to drink. We got back home…and, well you get the idea.

Normally I think I could handle this. Spending the night with someone doesn’t mean you have to get married or anything. The problem is, we both decided to try and make a go of an actual relationship. I realize this was a mistake now, but at the time it made sense.

Anyway, it was nice for about a month, but now things are really screwed up. In reality, my relationship with “Ann” is at a point were we barely speak to each other. I really have no idea how THAT happened! All I can say is that being friends with someone and dating that person are totally totally different things. It doesn’t help that she’s VERY hard to talk to.

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Just trying to help on August 24, 1998…

Dear Breakup Girl,

I have a female friend, K, who is dating R. Well, sort of dating… she’s been trying to end it for about 6 months (that would be about 1/3 the time)… the problem is, she cares for him, and she senses how much he cares for her, and feels guilty trying to end it. So there I was, minding my own business, just being her friend… and I saw how hard she was struggling and, being the enabling personality I am, I got to helping her deal with some of her self-esteem issues etc… and we got to be closer friends… now — before you think you know where this is going, we’re still just friends… but we’re friends in a way that I’ve never been friends with anyone — and the closeness of it disturbs both of us at times…

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