Q. There’s a friendly checker at my grocery store who chats up everyone who goes through her line. She’s at least 20 years younger than me. Yesterday she said “How come a cute guy like you doesn’t have a wedding ring?” I pretended not to hear her and fumbled my way through the transaction, but now I am wondering if it might be possible she is actually interested in me. How do I proceed without making a fool of myself? – Long out of the Dating Game

Dear New Dater: The next time you go through the line, say “Hey, you! You really threw me the other day when you asked about my wedding ring! Did that mean you’d have coffee with me if I asked?” If she goes for it, be prepared to name a time and day. If she doesn’t, say “Damn! I knew it was too good to be true!” and give her a big smile. The odds of success will go way up if her manager is not lurking nearby.

–O!Connor