—Lost and confused
I don’t really know the circumstances of your crush, but depending on how well you know this girl and how often you run into her, messaging her couldbe perceived as somewhat creepy. For instance, if you run into her often and she never remembers who you are, or you always sputter incoherently when you do, then not even the wittiest Facebook message will probably lead to nuptial bliss. If you have mutual friends, however, then use that as your “in.” If you have a mutual anything, really—a mutual class, a mutual neighborhood you live in, a mutual coffee shop you frequent, a mutual miniature horse fascination. Whatever. If you have something in common, you’re much less likely to skeeve a somewhat-stranger out.
Some first message topics to avoid:
Love and/or your future progeny
Politics (unless you both work in that field)
How you’re 30 and have never been in a relationship
ReligionHow great she looks in that bikini picture from 2007 (or anything else that would indicate you’ve trolled her public images on FB)
Pop culture references
The latest weird/annoying thing Facebook has done
Make sure your message is short, friendly and casual. Don’t apologize or call attention to your possible creep-deepery. Also, when I say short, I don’t mean, “Hey gurl, wuzzup?” and that’s it. Give her a reason to respond. Ask a benign, non-generic question, again, possibly relating to a common interest you share, or even something that clarifies the mumbling when you ran into her last time. If you’re in any way charming or witty, use that in your favor, but if not, no worries. Just be yourself and be polite. If she’s worth her weight in pixels, she’ll write back to you. If she doesn’t, write her off, and move your crushing elsewhere.
Want to ask Anna an anonymous question about love, sex or dating? Email your quandary to firstname.lastname@example.org. Need to give your dating life a boost? Sign up for RedEye Dating. Pick dates, not people.