Mixing work and play on April 6, 1998…

Dear Breakup Girl,

I’m a single guy in my mid-twenties. I’ve been seeing this girl for several months, and everything’s been fine until lately. See, she’s my boss — mid-thirties, recently divorced (about a year ago).

I know she’s probably just using me, but that’s okay by me when we’re not at the office. But lately she’s been wanting to get, er, frisky…at the office, during work hours. That’s where I draw the line. We’ve always been good about keeping business and pleasure separate up until now, but I’m afraid of getting busted in the act and ruining my reputation at work. But I’m afraid if I break it off with her, she’ll trash my career. What should I do?

— Jake in Jacksonville

Dear Jake,

You’re right; getting “frisky” at the office will not put you on the short list for Employee of the Month. Then again, neither will dumping your boss.

Oh, Jake, what were you thinking?! See, you guys, that’s why I’m telling you that whatever you pursue at the office has to hold promise of an Actual Relationship, not just Adult Xeroxing.

Bail, bail, bail. And pray that she doesn’t retaliate. If you do wind up having to leave, well, let’s just say that BG is not convinced that you had wholesome, promising growith opportunities at Disclosure, Inc. in the first place. Also, remember that if you interview elsewhere, you’re going to have to tell them why you left your previous job. I’d fib.

Love,
Breakup Girl

Getting nothing Donne on April 6, 1998…

Dear Breakup Girl,

This isn’t a breakup question. It’s a get together question, but you handle tough relationship questions so well that I know you’ll do me right. I am in a sensitive situation (at least it seems that way to me), and I am so busy thinking about the right thing to do that I can’t seem to do anything.

I am slowly going crazy for a younger woman who I supervise at work. She is beautiful, sweet, interesting, motivated, and very captivating to me. I think that the energy is there working both ways, but how do you know for sure without testing it? She meets my gaze so direct with quivering eyes, she does nice little things for me she doesn’t have to do, and she even gave me a little hand-written, contemplative poem recently. The thing is that she is very nice with everyone, and in my position, the last thing I want is a harassment situation at work. Even more, I don’t want to come on to her and end up making work a difficult place for her to be.

My friends give me different advice. Two think that this could be a real good thing if it would work out the way it feels for me, so I should do whatever is necessary to find out. Another thinks that I have a responsibility in my position to keep “hands off” regardless.

Am I roping myself up too tightly? Where is the right place for a guy to draw a line for himself?

— Jeremy

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PLEASE read (BG alter-ego) Lynn Harris’ new article for match.com if your online profile looks anything like this:

Me: otherwise easygoing SF, 29, in desirable neighborhood near excellent schools and world-class cheese market. You: 31-36, Ivy League (except Penn), minimum 5’ 10″, maximum 180 lbs., pectoral-to-waist ratio .33; fiscal conservative/social liberal; profession: law, medicine, banking (employer must have innovative paternity leave policy); hobbies: pan-Asian cooking, helping the needy, foot rubs; civil to (but not “friends” with) ex-girlfriends (maximum: 2); informed, witty, self-starter: equally comfortable chatting at state dinners and changing tires. Send introductory email along with photo, high school and college transcripts, 3 recommendations (1 academic, 1 professional, 1 non-threatening friend-girl) plus two 750-word essays on the topics: (1) “A Man of Quality is Not Threatened By A Woman For Equality” and (2) “Why I Always Share My Feelings.”

Working it on April 6, 1998…

Dear Breakup Girl,

First off, YOU ROCK!!! OK, now to business. There is this guy at work who is a Major BABE. (I rarely use that word but in this case, it fits). We have recently become Great Friends. We hang out all the time and are constantly doing things together. I have to say that he is not only beautiful on the outside, but on the inside!!!! Anyway, everyone at work is in love with him, and he is hanging out with me. My problem is, I am starting to really feel for him. And I don’t know what to do.

On one hand I think, Yeah I should be happy being his Friend (I hate that word). And on the other: He is the one I have been looking for. He is the greatest guy. Any woman would be very lucky to have him…. It needs to be me !!

Should I do anything?? At the worst, we will be life long friends, at the best we will grow old together. Breakup Girl, I need your words of wisdom. Do I tell this guy what he means to me, and risk the chance of messing up the friendship?

Or keep my mouth shut and drool every time we are together?

— Margaritaville

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A nice surprise on March 30, 1998…

Dear Breakup Girl,

How and when do you know when’s “THE” time to confess your feelings for someone? I mean, it seems weird just to bring it up in a typical conversation (i.e. How’s your day? Oh BTW, I think I love you”). I also don’t want to put her under any pressure, which may be unavoidable … but one can hope, right? Thanks for listening.

— Phillip

Dear Phillip,

Correct.The reason why it seems weird to shoehorn a declaration of love into a typical conversation is that a declaration of love is not typical conversation (unless you’re a character in the movie Showgirls, where you would not believe what passes for typical conversation). So yes, time — along with place and context — is key. But Breakup Girl doesn’t have quite enough facts. From the way you describe it, it sounds like this “I love you” might come as a bit of a surprise to your intended. I mean, are you “confessing” your feelings in an existing relationship — or are you asking someone out? In the latter case, I recommend starting off with “How’s your day? I love … the Coen brothers. Want to see the Big Lebowski with me?” If you two have already got it going on, then pop the confession at a pleasant — but not overly orchestrated — moment. Not an all-out ambush; just a nice surprise.
By the way, I think you just intended it as shorthand, but one detail in your letter compels me to issue this warning: anyone who says things like “BTW” (and “LOL,” etc.) in actual verbal conversation is going straight to Breakup Jail. Especially if you’re a character in Showgirls II: Virtual Vixens.

Love,
Breakup Girl

Drawing it out on March 30, 1998…

Dear Breakup Girl,

For the duration of our nine-month relationship, my ex tried to convince me that we were “meant to be.” Without warning or reason, he then dumps me citing the “I love you but am not ‘in love’ with you” excuse. Whatever. Aside from one business like letter he sent a week post break up (and an angry follow up phone call on my part), we have not spoken since and it’s been six months. I am over him and the break up was definitely for the best, but I wonder now if this was the most healthy way to handle things. Although the lack of contact helped the healing process, would it have been better to have long, painful phone conversations analyzing what went wrong just so I have a clue? Do you advocate the “cold turkey”/no contact approach even in the absence of a concrete breakup explanation?

— B.

Dear B.,

A “long, painful phone conversation” does not a “concrete breakup explanation” make. Trust me, you didn’t miss much.

Love,
Breakup Girl

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 answers What Should I Do in L.A. who’s stymied by a boyfriend who portrays himself as single online. But since he’s never met the women he chats with IRL, it’s not so much the cybercrime, it’s the coverup:

The first time I caught him, he said it was because he needed someone to talk to. The second time, he said he was trying to catch me cheating.

Yes, this one is more about trust issues than cheating. Read the full letter at Happen magazine, then add your two cents in the comments below.

A real classic from March 30, 1998…

Dear Breakup Girl,

I have good news and bad news. The bad news is that I have recently been dealing with a difficult breakup. The good news is that it’s not mine…

My boyfriend’s ex is, well, a psycho hose beast. Before we were dating, they had broken up, but she was still causing him a lot of pain and suffering. He was obsessed with her for a while, and then he finally seemed to be letting go of her. A while after that, we started dating. Things were mostly OK. She would come up in conversation occasionally, but I never felt seriously threatened by her. I know that she is bipolar, and can be a very nasty person for no reason.

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Caring too much on March 30, 1998…

Dear Breakup Girl,

My live-in boyfriend (who’s 30, I’m 41) of three and a half years told me he wanted to ‘just be friends’ this past September. I moved out. He got engaged New Year’s Eve to a woman (she’s 29) with whom he had a brief fling in college and has heard from or had visit him a couple times a year for the past nine years (each time they met, she was all over him like the proverbial cheap suit). They are to be married in May. I have two questions. Will this marriage work? and Why do I still care?

— Patton

Dear Patton,

Why do you care? Of course you care. Are you kidding me? Even Breakup Girl cares, and she doesn’t even know these people. Dumped you in September, engaged in December?! Yeesh. All I can say is, she may have been all over him like a cheap suit, but oddly enough — as the genuine-article fashion zombies from the 70s and 80s attest — sometimes it’s the cheap ones that last.So this thing could be a flimsy rebound, or it could be some solid perma-crease that somehow never got ironed out. Or, gulp, it could be an age thing. So I don’t know if it’s going to last or not, but I do know that you’re not allowed to obsess about it. Write to Breakup Girl, speculate with your friends — but I can trust you not to pull any “I must stop the wedding” Julia Roberts antics, right? Buy your bad self a pricey suit and find some gent who doesn’t have his past mixed up with his future.

Love,
Breakup Girl

Another good bi from March 30, 1998…

Dear Breakup Girl,

Ohmigod! This guy, my kinda friend, just told me he wants to ask me out. He’s really strange. He’s a bisexual, which is totally cool with me if we’re friends, but not as a boyfriend. He paints his nails and dyes his hair and carries around hair cream. The whole thing just kinda creeps me out. I’m really spazzing now because it is so odd to be around him. To tell you the truth I don’t even like him that much! I feel really bad but! Ahh help me please!!!!!!!!!

— SOOOOOOO Stressed

Dear SOOOOOOO Stressed,

Ohmigod! Relationships are, like, complicated enough, even when they start out on the right foot. But believe you me — and I think you’re catching on to this — “I don’t even like him that much” is soooooo the wrong foot to start out on, even if the toes thereupon are sporting some phat shade of Hard Candy. So if you do want to hang with him, say, “Hey, thanks a million, I’m not sure dating would work, but hanging out would be great,” and then walk the talk. If you don’t want to hang out with him, say, “Hey, thanks a million, I’m not sure dating would work.” And let me leave you with one question: is it odd to be around him because you’re profoundly concerned for his feelings, or because — much the same way Cordelia used to find it “odd” to be around Buffy, Willow, and Xander — the only vote he’ll get for Popularity King is from the hair cream lobby? Think about it.

Love,
Breakup Girl