Here, your weekly installment of Ask Lynn, BG’s alter ego’s column at MSN.com (powered by Match.com). This week — continuing on the theme of hope — we meet A Hopeful Dreamer, who has been waiting, like, forever, to ask this girl out. The problem? She’s always been with someone else. Now — yeehaw! — she’s just broken up with her boyfriend of two-plus years. So AHD wants to know: when is it cool to ask her out? Now? Now? Okay, how about now?

But really, you see the problem: ask her too soon, and he’s doing the old HEARD YOU GUYS BROKE UP SO SORRY opportunistic swoop (or is he?) — or just setting himself up as Mr. Rebound. But ask her too late and he’s … too late. Read the letter and response to find out when Lynn gives the green light — and then come back here to comment!