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, so now you’ll get two new letters each month, starting with…

1. Do I Have To Lose Him, Too? has become close with the boyfriend of her friend who died of cancer. Now that its turning romantic, she worries what others will think…

Needing a Hollywood ending on January 19, 1998…

Dear Breakup Girl,
My best male friend and I got together for a short time about a year ago. He’s had some bad luck with girls in the past and is afriad of losing our friendship if we broke up. (Needless to say, we ended up back as friends fairly quickly regardless of the fact that everyone else says that we’re perfect together.) Now the complicated part is that he has been going out with a (FORMER) good friend of mine for several months and thinks he’s going to MARRY her! What should I do? I feel like I’m living out “My Best Friend’s Wedding!”
— Lost

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A friendly note from January 19, 1998…

Dear Breakup Girl,
I am stuck in this oh-so-popular position: I have a million guy friends that are guys, but “friend” is all I am to them. I have dated a thousand guys, but all of them break things off saying that they do not see me as a girlfriend. The girls often do not like me either, as I am their boyfriend’s best friend. What should I do? I wish I could find someone to be serious with, but no one wants to be serious with “one of the guys.” HELP!!!!!!!!!!
— Just a Friend

Dear Just a Friend,
SEE, EVERYBODY??? Breakup Girl will say it again: the “nice”/”friend” thing is not only a Guy curse. And I’ll say this again, too: Could be that you’re the kind of person for whom serious relationships start out as friendships. Trust that that’s the case, and the “serious” part will evolve when the time — and the match — is right.
Love,
Breakup Girl

A photo opportunity on December 29, 1997…

Dear Breakup Girl,

I really like this guy and I’ve asked him out before but he never answered. Other people have told him that he should go out with me but he never gave them an answer either. I am the only one of his friends who received a large picture of him for Christmas; everyone else got wallet-size. I feel all special — but I don’t really know how he feels and I don’t want to ask him out again because I don’t want to lose him as a friend. Please help!

— Nichole

Dear Nichole,

Breakup Girl is unfamiliar with — but intrigued by — this practice of giving photos of yourself as Christmas presents to people who are not your grandparents. I’ll trust you when you say that it’s possible to measure someone’s feelings for you in terms of surface area. But since he has not leapt at several obvious chances to go out with you, Breakup Girl wonders, gently, if the thousand or so words that that picture is speaking might go something like, “I know you like me but I really just think of you as a friend. I feel bad about that — and I do think you’re special — so I want to make it up to you and show you that by giving you a larger photo than everyone else.” See? So let him know you appreciate the photograph (don’t tell him it’s under your pillow), and focus on the friendship. If something more is meant to develop, it will.

Love,
Breakup Girl

Awwwwww from January 19, 2008…

Dear Breakup Girl,
I’ve been friends with this guy at school for three years, and until now I’ve always thought of him as just a friend. He and I went to a formal dance, and even my mom thinks that we are dating. When I told him this, he said, “Maybe we should be.” That’s when I realized that I have a crush on him. Should I pursue this and try to start some kind of relationship that’s “more than friendly”?
— I Think I’m in Love

Dear I Think I’m in Love,
As far as “signs” go, that’s about as good as it gets. What are you waiting for?
Love,
Breakup Girl

In high school, asking out a friend can become a big production…

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