MSN.com, Match.com, HappenMagazine.com: they’re in a healthy and satisfying 3-way relationship. Meaning that you can find MSN/Match.com’s “Ask Lynn” columns –penned by BG’s alter ego — over at Happen now as well.

This week Lynn hears from a gal who’s scared-to-lose him, but she’s was burned by a cheater before:

I got out of an extremely bad relationship about three months ago with a man who cheated on me. I thought that I was going to stay single for a long time because I knew that I would have a hard time trusting again, yet that’s not how things worked out. I became friends with someone shortly after the break-up, and the more time we spent together, the more we both realized that we were meant to be together.

Now she’s grown suspicious of this new love and it’s driving him away. Is she unable to let the past go and what should she do? Read the full letter and response at Happen, then chime in with your own thoughts below.

Making a move on November 2, 1998…

Dear Breakup Girl,

I guess this question isn’t too hard to answer. I’ve liked this girl, let’s call her Joan, and for four years now I’ve been crazy about her, but I never had the guts to really go for her. I’ve since supressed all my feelings for her because I don’t feel I’m good enough for her. So, NO ONE knew that I had these feelings for her. Joan’s the sweetest, kindest, most beautiful, most perfect girl in the world, but she’s just a regular friend to me and that fact is killing me.

I’m not the ideal guy for girls. I’m the quiet guy who no one really bothers to talk to (hardly popular), except to ask for help on a homework assignment. I guess you can call me a nerd, but I’m not that dorky. Her friends can stand me, but they don’t really enjoy my company if you know what I mean.

Well, I know for a fact that Joan doesn’t like me in that special kind of way, and I need to find someway to let her know how I feel without completely scaring her away. I don’t want to lose her friendship. I talk to her whenever possible about little things and I spend as much time as possible around her without seeming conspicuous. I call her from time to time just to talk. I make up some excuse and ask about what assignment we got from which class and then go onto other, more casual things.

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Chasing perfection on November 2, 1998…

Dear Breakup Girl,

HELP ME! I have been in love with…let’s call him “Jeff”…for ALL OF MY LIFE! Okay…just six years of my life. We attend the same church, but just this fall he moved to Indiana to go to college. He’s soooo fine…and sooo smart….and sooo dedicated to God (can’t find a guy like that just anywhere, can you?). Anyway, I’ve tried to keep my obsession secret, but the ENTIRE church KNOWS! Even his family! His mom and sister and grandmother all love me to death and even invite me to family functions…and to pick him up at the airport this weekend. *happy sigh* I didn’t go, though. *sad sigh* In the entire six years I’ve loved him, he has spoken to me…maybe 10 times. I know it sounds crazy…but I feel such a connection with him. Like we’re meant to be. Only he doesn’t know it…yet.

What should I do, Breakup Girl? No guy I know or could EVER know could be as wonderful, or kind, or compassionate, or PERFECT as Jeff. I compare everyone to him…and no one could ever take his place in my life. He is the MAIN object of my affection.

I know, I know…there is no hope whatsoever. The longest conversation I’ve ever had with him is when I asked him what he was bringing to a party. I also know he knows about my crush on him. It’s SO obvious. But today!!! GET THIS! HE WAVED AT ME! (Go me, go me…go Jeffy!)

Is this all so immature? I’m not some silly junior high girl. I’m a junior in high school for crying out loud! Do I just have some strange mental complex that makes my knees go weak just at the sight of Jeff?

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Feeling shy on November 2, 1998…

Dear Breakup Girl,

Well, I like this girl my friends introduced to me, and I am so obsessed with her, I almost ran away from home just to see her outside with my friends. I doubt she feels the same way too, and I’m always depressed when I can’t see her, and I don’t want to call her cause I think she might say I’m annoying, and I want to get over her, but I don’t think I ever can. I really want help. My school marks are falling and I can never concentrate because I really like her, the only way she said she would go out with me is to get to know me better, but I’m way too shy. If I can’t win her, I’ll need all the help in the world to get over her… I don’t think anything or anyone can get my mind off of thinking of her for at least 1 second — I really love her!!!!!!

— A Depressed Soul

Dear Soul,

Uh-oh, kiddo. Do you see the itty bitty problem you’ve set up for yourself here? This girl gave you your mission — to let her get to know you better — but if you say you’re too shy to try, then you’ve already chosen not to accept it. That’s the immediate problem. The other stuff to think about, according to Belleruth, is this (it’s heavy stuff, take it slow):

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Taking a break on November 2, 1998…

Dear Breakup Girl,

I’m a 31 year old woman/girl who has been happy to be single for about 1.2 years. For the first 1.0 years I was very happy to not be attached to someone. I have had some very unhealthy relationships in the past, (starting at age 17) and this present break from the pain and the passion and the excitement and the horror and the sex and the waiting, waiting, waiting for the phone to ring syndrome has been the most productive and stress-free period in my life so far (not including before doing the rude thing with boys period)

I have sorted a lot of things out and feel very strong but I have found that during this period of single-hood, there has always been someone on my mind that I have fixated on, making me feel as though I do have a love life when actually I don’t, and…the thing is, now I wonder if I’ll ever be able to behave maturely in a relationship with anybody that I actually know, and indeed, if I’ll ever find anyone with whom to behave maturely with in a relationship. As you are not psychic, I suppose I need to ask a more specific question regarding my predicament/Lerve Question:

How can I stop myself from clinging to ridiculous fantasies about guys I hardly know and then feeling really stupid when I find out (after months of building up the fantasy) that they are Married, Gay or just in need of a babysitter. I seem to thrive (until they dissolve) on these psuedo-relationships in which I don’t actually know the guy but feel content and fulfilled just thinking about how gorgeous they are and how excited I am about seeing them next. Could it be that I have these fantasy relationships to protect myself from the cruel world of relationships that I have experienced in the past? Probably yes. And is it the case that I have a problem with getting to know and like men at the same time. It seems that the more I know a guy, the more I see their imperfections — things like the way they chew their food or hold their pen. Why am I so picky about minor details but have, in past relationships managed to forgive massive personality flaws? As you would say, Breakup Girl, one big fat Hmmm…

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Last week, Breakup Girl happened to talk to an adorable 15-year-old named Emily in Charleston who wanted to go as Rose from Titanic for Halloween. Partly because she would get to wear a most excellent dress (and also spit); partly because, in her words, “I am completely in love with Jack Dawson.”

Teens swooning over Titanic? Slow news day, Breakup Girl?

Stay with me. Actually, most teens have already weighed anchor and docked their obsession elsewhere. Anyway, Emily knows she’s behind the tide: “I still watch my video once or twice a week,” she said. “But I realize I’ve gotten to the point where I have to stop talking about it.”

Fortunately, she went on. What does she love about Jack? “He’s so free-spirited and self-confident,” she says, reciting entire movie scenes, line by line, to support her point. “He’d break the rules and do anything for Rose. And he looks really good in a tux.”

Is Emily going to date Jack Dawson? No. With him as her ideal, is she now locked in to holding out for someone who will run into a sinking ship/burning building/dinner with her parents to save her? Well, that would be nice. But is all of this teen obsession — which, you all, is different from grownup obsession ONLY in that adults are less likely to use scotch tape on their walls — silly, pointless, or worse, false-hope-building? Is this all foamy Calgon that will take you nowhere? Not necessarily.

Because: do Emily’s voyages of fancy help shape her sense of what she wants from love, life, and her neighbors’ candy, back on land? Yes. Welcome to this week’s theme:

We all have our “ideal” partners: David Duchovny, Lara Flynn Boyle, Lara Croft, The President of the United States of America, Breakup Girl, our first love, the one that got away. And we all have … our real lives. Clinging to a larger-than-life fantasy can loosen our grasp on — and appreciation of — what we do or could have, or keep us from having it in the first place. And, when the ideal meets real, the practically inevitable result: crushing letdown.

All true, yes. But Breakup Girl is not going to give you guys some boring finger-wagging Get Real speech. Because BG thinks that overly cautious hardcore get-realism throws out the babe with the bathwater. And she does want you to expect and deserve to be with someone freaking fantastic.

So instead, consider this Important Breakup Girl Maxim: FANTASIES ARE DATA.

So whether your idealized lover is someone you’ve glimpsed, met, dated, or downloaded, ask yourself these questions:

Who’s there? What is it about this person, really, that fascinates you? Think about it, really. Ask them to kindly step down from the pedestal so you can see what writ-large characteristics you’d actually ike to have on your level. We are talking actual human traits. Not, like, just “Cuuuuuuuuuuuuuuuuute!!!!” or “I just really admire the way nothing comes between her and her Calvins.” Emily, for example, was specific. So specific I didn’t even have room for it all. Words like “free spirited,” “confident,” “devoted.” (Yes, “tuxedo,” too, but that was last.) Look at what you’re drawn to, for better or for worse, and think about why. Disassemble your ideal; keep the pieces you can really use. This is real information, you guys — about what you truly love, about what you might feel you lack. Which brings us to:

What’s missing? Anyone see Cupid week before last? (Just for the record, lest you now think that she sits around watching TV instead of flying to your aid, BG has seen Dawson’s Creek and Titanic each only once.) (Okay, while i’m at it, if you’re not watching that genius show Sports Night, you’re missing something major.) ANYWAY,Cupid. In addition to a subplot about first loves, the show was about a woman — a transplant to Chicago from the ranches and canyons of the West — who had developed quite a “relationship” with the rugged Marlboro-type man on the billboard outside her office window. Cupid, doing his job, set her up with the actual model. Everything went swimmingly until she discovered that he wasn’t like her (or his larger-than-life image) campingly, ridingly, hikingly, mountainbikingly, etc. Crushing blow? Only slightly. Important information? Yes. This dalliance not only helped her realize just how truly important it was to her to pitch her tent with someone who … can pitch a tent; it also showed her that she was fundamentally unhappy in the city and really just needed to get the hell outta Dodge — with or without a cowboy to take her away. Aha. To switch abruptly over to hockey imagery: focus on the empty space around the goalie. What does this person’s commanding presence — or absence — distract you from? When the spotlight’s on them and their pedestal, what’s going on in the dark? Shine your flashlight into those corners and see what you see.

A version of this column was originally published November 2, 1998.

Unsettled on October 26, 1998…

Dear Breakup Girl,

I have been widowed 14 years and have been seeing this widow for 12 , yes, 12 years. At first it was great and we have had great times, but over the years I always felt that my needs were not met and she finds it difficult to talk things out. I’ve made my needs known and quite a few times she would try to change and would for a while, but would then go back to being unaffectionate and not thinking about me and not doing all the nice things I do to her and for her. She cannot share her thoughts and feelings and I never know what is on her mind. If we have a disagreement she puts her head in the sand and thinks it goes away. If I go on a trip I bring her back a little something. The times she’s gone away, she didn’t think enough of me to bring a little something, even like a rock or some dried flowers from where she was. I have had to beg her for any little kindness or consideration, which she has come to expect from me and which she does get.

I made out a form and asked her to share herself by filling it out. It had 4 parts:

#1 What can I expect from this relationship?

#2 What do I get from this relationship?

#3 What can I do to make this a better relationship?

#4 What can my partner do to make this a better relationship?

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Unrequited on October 26, 1998…

Dear Breakup Girl,

There’s a girl whom I really like that I met this year at college. She has a bf who is in the Navy who is thousands of miles away. I know she really cares for him, and loves him. I don’t want to come between something like that. I don’t want to be the jerk who breaks up a good thing. But I can’t help but feel the way I feel. When I’m around her, I feel so alive. At the same time though, she is a really good friend. I feel like I can open up to her about anything, but what I don’t feel is the same from her. How do I go about showing her I can be one of the greatest friends of her life without flirting with her, or making her feel I want a closer relationship out of it. I mean, I do, but right now all I really care about is strengthening our friendship.

Then maybe if things were meant to be, something will come out of if. If not, then I’m happy just being friends. My biggest concern is that once the semester is over and I don’t have any more classes with her, which I’m sure I won’t, it will be difficult finding reasons to call her or go to her place. Thanks.

— Hopeless in Hartford

Dear Hartford,

Okay. Don’t overdo it, but go ahead and do all the things that I always yell at the accursed Friend-Boys for doing. Do nice stuff for her. Do fun stuff with her; do not touch. Build her a loft, for all I care. And/But if you find yourself without a good reason to call, then don’t. Instead, find a reason to call someone else. And ask her out.

Love,
Breakup Girl

The family that plays together on October 26, 1998…

Dear Breakup Girl,

I have been dating this girl Meaghan for 1 month. When we went out clubbing the other night her brother Zach came too. That was cool, cause I am friends with him, I have noticed that Meaghan and Zach are close which is good, but tell me if this is something to be concerned about….

If you were watching us in the club that night you would have thought that they were a couple and not Meaghan and I, first they were talking to each other all night long and not really involving me in their conversation — that was ok, they are Bro & Sis. Then they walked together, held hands, gave each other hugs and even pecked each other on the cheek here and there!!! During all of this I received no affection at all. THEN Meaghan saw some friends and they came over to us, and she goes, “This is my brother Zach”…and then continued blabbing with them without bothering to intoduce me, like I wasn’t even there!And I was standing next to Zach. That was it for me, I left them, got a drink and went mingling. What the heck would you think was going on? YEAH, I know…Their family seems close…REALLY close!!! Do you think I’m just paranoid? I live with my sister and I love her to bits, but Meaghan and Zach seem to give me the willies…Would I be a dick for breaking up with her? And how exactly would I do that without implying anything? Thanks —

— J

BG chimes in after the jump!

An international incident from October 26, 1998…

Dear Breakup Girl,

I’m a 28 year-old single woman with a house, a garden, a couple cars, a PowerMac — the whole nine yards. At long last, I can finally say I’m as happy as I imagine clams must be, what with that handy calciferous shell and all. I mean, sure, I’d like a guy to bum around this wacky planet with, but it’s no big deal. For real.

Anyhow, around the first of the year I met this guy (he’s 31) from another continent on the Internet. I knew he was far, far away, so I didn’t take it seriously at all. But Around-the-World Boy had other emotional ideas, and I got a little swept along. After about four months he decided he wanted to come visit me. It seemed like a zany, romantic adventure and I was really looking forward to it — but he bailed at the last minute, saying he “didn’t feel the same all of a sudden.” For the first time in my life I heeded those big, red bells clanging away in my head, cut my losses right there, and told him I didn’t think we ought to write anymore. A teary, sorta embarrassed (I mean I met him on the *Internet*…) call to mom, a pint of coffee Haagen-Dazs, and a couple margaritas with the gals later I was already starting to forget it.

Flash forward a couple of months, and what should arrive but some mail from ATWB saying he’d been thinking about me. So I replied in a just-friendly kind of way, and we’ve been writing to each other a few times a month ever since. In the meantime, I’d made arrangements to use my frequent flier miles for a free overseas vacation. Since ATWB and I had once discussed meeting in the country I’m going to (I’ve wanted to go there for years), I debated not telling him that I was going because I didn’t want him to think it has something to do with him, which it honestly does not.

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