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

This week Lynn advises Maybe Not So Mature? who can’t stop thinking about her fling with a younger man.

I cannot stop thinking about him. It’s driving me nuts! This is not what I need because I am finally ready to date after being divorced over a year and dating losers for six months. I feel weak for sitting and hoping that he calls.

Is she putting too much emphasis on this dalliance and should she feel bad about that? See if you agree with Lynn’s advice, then come back here to comment!

A moving response on March 2, 1998…

Dear Breakup Girl,

I dated this guy for six months. I’m 40, he’s 25. We were getting along so great — then as soon as I let down my walls, told him I had feelings for him, he broke up with me. He’s moving away and doesn’t want to have anything to do with me anymore. What’s the deal? Plus, I hate being broken up with by e-mail … what a coward. .

–Deena

Dear Deena,

You guys have heard what I always say about the C-word. You know, Canada. Where people tend to flee to when they feel like they’re about to have to make a commitment (for Canadians, it’s Cleveland). Which is most likely what happened with your young buck. And in this case I think it was more a function of age (sowage of wild oats surplus, yada yada yada) than of gender.

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May … September … February 9, 1998…

Dear Breakup Girl,

I have been seeing a much younger man for about two years now (he’s 28 and I am 58). We are really crazy about each other but I am afraid that I may offer him more of a mother-figure relationship than one of a lover. We haven’t talked about “where we are” lately, but should I let him go, or make something more permanent out of it? Yes, I mean marriage. Would it be fair for someone my age to try to wed a young stud like him?

— Darry

 
Dear Darry,

Wow, that is a May-September thing (yeah, as in May 1958, September 1998). Let me ask you this: are you worried about the mother-figure thing in principle, or in practice? I mean, does your concern stem from a vague “Is this weird?” notion — or from some actual dynamic you guys have (e.g. when he didn’t call to say he’d be late for dinner, you took away his phone privileges). Or, for that matter, is there some Freud-oid episode in his past (oh, say, loss of his mother) that might predispose him to seek out a substitute? Or one in your past that might predispose you to be that substitute?

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A foreign occupation landing January 28, 1998…

Dear Breakup Girl,

I met a girl 10 years younger than me about three weeks before being sent to Bosnia with the military. She moved into my apartment and is taking care of all my affairs. I have found that she drives me up the wall and I know for a fact that she isn’t the one for me. However, she has our marriage and life all planned out. I have tried to get her to understand that she doesn’t even know who I am, but she says she will change her whole life just to please me. I hate this and I really would like to hear what you — as a super-female — would do?

— GI John

 
Dear GI John,

Gals, just a tip: if your man would rather be in Bosnia than at home with you, you two need to talk.

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Old enough now, but not on January 19, 1998…

Dear Breakup Girl,

Hi! I am a senior college student, and believe it or not, my boyfriend for ten months is just a senior high school student. Dig that?

Any way, I’ve been thinking about this for quite a long time. I always get paranoid and feel insecure in our relationship. Sometimes I feel like I don’t trust him anymore. Maybe because he has hurt me a lot, or he is just plain insensitive. Is it because he is still a kid? I think that sometimes, he is mature enough. Please help me.

— Betty Joy

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Ask Lynn, Breakup Girl’s alter ego’s advice column at MSN.com (powered by Match.com), is now being updated monthly rather than weekly (boo!) … but on the plus-side, you’ll get two new letters at a time (yay!). For January, we’ve got a gal with some office intrigue and a couple with trust issues…

1. Not Safe For Work is worried that dating her boss’s friend might affect her job

and

2. Haunted by Her Past has a girlfriend that is uncomfortably chummy with her exes, yet always checking his phone for the same behavior

Read the letters and advice, then come back here to comment!

Virgin/merry from December 29, 1997…

Dear Breakup Girl,

This Christmas I’ve been naughty AND nice. Two problems plague this romantic heart. I’ve been “nice” and supportive of an internet friend for two years now, the shoulder and the punching bag through thick and thin and foggy. We’ve met, declared long distance love on the eve and morn of our virginity, and been hunky-dory up till the twelve days before Christmas. But now the stuffing in my stocking is in another the-world-hates-me spin. My patience wears thin.

Now your favorite, the “naughty.” She’s 17, I’m 26 [you sigh here]. Girlfriends have been very rare on the granted end of my wish list (see: 26, virgin until recently) and the charm of this first girl only just began to wear thin/thick. Until now it’s been two kindred souls gulfed only by age and distance. I know my patience will be rewarded if I can only get back into the spirit of past, present and future, but it’s so difficult sometimes loving someone through monosyllables and gloomy glums. Time and experience will solve our yule-tide blues, but what can this elf do in-between seasons?

— Mikey Pooh in Missouri

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First, the “Accidental Cougar” — now, the on-purpose ones.

BG just stumbled across this oldish-ie but goodie in the Boston Globe Magazine by Erika Cann, who writes: “[A]s I hurtle toward 40, I find myself irresistible to younger men. While I used to be focused on 30- to 40-something mid-career professionals in Dockers, I find that in my pursuit of these “safe bets,” I’m tripping over young Zac Efron look-alikes who are falling to their knees. I have become an Accidental Cougar.”

Say what you want about the term “cougar” — what I want to say, for example, is: “How come we call women who date younger men ‘cougars,’ and men who date younger women ‘men’? — but that, really, isn’t the point of Cann’s charming piece, which is really about being open, adventurous, and patient in the safari of love. Go enjoy the rest after one more bonus teaser: “During this year and a half, I dated a handful of interesting guys all seven to 14 years my junior and was only once approached by a guy in my age range. I went out with him the same weekend I had a date with a 27-year-old, winding up at a string quartet one night and ‘Beerfest’ the next. I fell asleep at one of these events, but I’m too embarrassed to say which one.”

Friday tries to separate the men from the boys…

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