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