Style advice from October 12, 1998…

Dear Breakup Girl,

I guess that I am one of those “unapproachable” girls that you suggest that your readers try not to be. I am an attractive and active university student and I have many friends from different social groups. The problem is that I am old fashioned and WILL NOT ask a guy out (all right, I am shy too). It would be deceiving if I said that no one ever asked me out, but I guess I am looking for something other than what is being offered. I have been told many times that I look unapproachable, though. I wear a lot of black (but my hair is blonde); sometimes I think that changing my look would secure me more dates but then I realize that I shouldn’t have to change myself for anyone. My question is not “what is wrong with me,” but “what can I do (without totally changing myself) to make myself more approachable?”

— Tara

BG’s fashion statements after the jump!

Hungry for answers on October 5, 1998…

Dear Breakup Girl,

I have liked this guy (let’s just call him B) for about 6 months now (hey, that’s a long time when you’re 14!). He is always very sweet to me, and even though some others claim he’s a jerk, I don’t believe it. But that’s beside the point. Homecoming is coming up in a month. That seems like a very long way off, but everyone in my school is completely panicking about it, especially us freshmen. Let me digress for a moment and explain: B is in the popular crowd. I am in the semi-popular crowd. I’m one of those friendly people that’s not “bad” enough to be in the popular crowd but is still friends with them. I’m friends with the popular girls, and I try to be friends with the guys, but they don’t seem to be interested in me as anything more than a friend, if that. Anyway, yesterday B sat at my lunch table across from me. We got onto the topic about homecoming. He was complaining that everyone had been asked already. I told him that I haven’t. He said, well, everyone that he was thinking of asking had been asked (I don’t think he meant it in a mean way). He asked me who I would like to go with, and I wouldn’t tell him because I hadn’t even told my friends. He assured me that HE was my friend. The rest of the conversation isn’t that important, but I’d like to let you know that we talked the ENTIRE LUNCH PERIOD (I was so excited.). Do you think he meant this as a “I am interested in going with you to homecoming” conversation, or a “I’m really nosy so I’m trying to pump you for information” conversation? I’d like to know so I don’t let the word out that I’d like to go with him to homecoming and make a complete fool out of myself if he doesn’t like me. I’d also like to know, if this WAS actually a “interested in homecoming” conversation, how do I get him to ASK me? Or ask him? Please help, for I need some information fast!!!

— Homecoming Hell

Dear Homecoming,

I’d like to let you know that I spent your ENTIRE LETTER thinking you should go ahead and ask him.

Let me know what happens! He says yes, you write me back. He says no, you write me back. We’ll deal, girlie, no matter what happens. Fingers crossed! Good luck!

Love,
Breakup Girl

Un-mixed signals on August 31, 1998…

Dear Breakup Girl,

How do you get a guy to catch on that you like him? I”ve emailed him, called him, been to his house, even told his best friend, and what other people seem to think is that he likes me too. I understand that he just ended a sort-of relationship a week or two ago and that he says he doesn’t want a long relationship because he can’t stand people for that long, and I agree. I’d just like to try something to see what develops. I don’t know what more I can do besides walking up to him and outright telling him, but I’m still unsure whether he’s being deliberately obtuse or if he’s incredibly unobservant. We are both going to be seniors in the same high school so I will be able to see him hopefully occasionally at least (it’s very large). So, should I just wait for him to notice (which could be after we head off to college at this rate) or attempt something a little more direct?

— Brittany

Dear Brittany,

He knows.

Next!

Love,
Breakup Girl

A happy ending on June 8, 1998…

Dear Breakup Girl,

Just something to add to your great Prom series. When I was at the age of worrying about prom dates, I found myself in the situation of having no steady guy to ask. I also knew that if I didn’t do something soon, I would probably end up going alone.

What did I do?
I took my future into my own hands (something that took a lot of nerve) and walked up to this guy i was fairly interested in. And amazing things happened! He was a friend of mine, but not one of those really close friends. I asked him if he hade a date for the prom (even though I knew full well that he didn’t). When he said he didn’t, I asked him if he would like to go with me. He said yes. What happened next is the truly amazing stuff. He suddenly started paying a lot more attention to me than he previously had, joining the backstage team I was on, sending me letters, and just generally being a nice FRIEND. At some point between the date of asking and the prom, we started going out together. We actually went out for FIVE years. The moral of the story? Just go for it. You never know what might happen.

— Sam

BG responds: Who-hoooo!

Asking for it on June 1, 1998…

Dear Breakup Girl,

Two questions.

1. During a discussion with one of my many platonic female friends, I mentioned that I’d seen a cute girl at the gym. Normally, when I see a woman that I want to meet, I strike up a conversation with her. As long as the lights are on, it doesn’ t matter to me whether or not she’s sweaty (within reason, of course). I guess what I’m saying is that I wouldn’t think twice about talking to a girl at the gym. My friend had said she wouldn’t date anyone she met at the gym; that she just goes there to work out and that’s it. What are your thoughts on this?

2. Whenever I read one of those “what do women look for in guys” type polls, “sense of humor” is almost always one of the top three qualities. Why, then, do so few women have a well-developed sense of humor? I’m sure they’re out there, but I’m not meeting them. Very few women can tell a good joke. And the ones that can are usually married. Why is that?

— Rocket from the Couch

(more…)

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 aides a gal who might Need Closure. You see, she was interested in her younger boss but he always resisted any office romance — or was that just an excuse? Anyway, now she’s quit and …

Since I left his office, I have dropped 20 pounds (more to go) and had what my friends call a “makeover.” Should I give it one last face-to-face shot—or just walk away for good?

Do you think this is the right strategy? Read the full letter at Happen Magazine plus Lynn’s response, then add your own thoughts here in the comments below!

Reading the signs on April 20, 1998…

Dear Breakup Girl,

I’m just wondering: if a girl whom you have known for a year suddenly tells you that:
a) she broke up with her boyfriend
b) you’re born under the same astrological sign (birthdays one day apart) as her ex-boyfriend, and
c) apart from that, however, you’re nothing like him,
What does this mean?

She likes you? Yes, no, maybe.

— Tiger Man

Dear Tiger,

Yes, she likes you. But if you want to be safe, I’d wait until Rebound goes into retrograde.

Love,
Breakup Girl

A quick answer from April 6, 1998…

Dear Breakup Girl,

I went out with this girl once and whenever I try and ask her out again, she always makes a grossed-out face and walks away before I even go up to her! I don’t know what to consider that other date since she hasn’t said anything about it. What does this all mean?

— Ji

Dear Ji —

I think she’s doing The Rules! Go for it!

Love,
Breakup Girl

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

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