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Q. I’m in my 40s, divorced, semi-frustrated with dating apps, and hoping to meet somebody in person naturally. I’m doing my best to just put myself out there. I’m not shy and typically don’t have trouble finding a date or two. I work part time at a restaurant/bar-type place and began chatting with two women, one of whom was single and amazingly attractive. I was excited when she asked for my number and I happily obliged.


Admittedly, I broke cardinal rule number one, which is to get a number as opposed to give a number. She seemed genuinely interested (albeit maybe she had a bit of a wine buzz) and promised she’d drop me a text once she got in an Uber that evening. Still nothing 10 days later. Obviously she wasn’t genuinely interested . . . or maybe shy or embarrassed? I haven’t stopped thinking about her. I only know her first name and the part of town she lives in. I really thought I’d have heard from her by now. At what point should I just give up hope and move on?

— Waiting

A. She’s not a real option until she makes a move. So many numbers are exchanged without follow-up. So many people say “I’ll text!” but never do. It’s possible she chickened out — or maybe she wasn’t as single as she said she was.

If this is about embarrassment or self-doubt — or about her getting the wrong number somehow — she can return to the restaurant to feel things out. It sounds like you’re pretty easy to find.

For the record, I don’t think you broke any sort of rule here. She asked for your number, which means she wanted the power to make (or not make) the next move. I’m not sure that you texting her would make her any more responsive.


You mention that you know her first name and where she lives in town. Please do not try to seek her out. Do not convince yourself that it would be romantic to walk down a street in Framingham (I just decided you live in Framingham) screaming, “Stephanie! Where are you?”

So much of a relationship is about showing up. You want to know you’ll be with someone who does the work to keep things going. Until she does that, she’s just a good story. — Meredith


Bartenders/waitstaff talk people up to get better tips, but sometimes patrons talk up the bartender to get better service. BLISTERED-TOE

I wouldn’t necessarily give up hope but I wouldn’t put any effort into holding space for her or trying to find her. Keep trying to find dates. You’re likely to meet someone better anyway. SUNALSORISES

“At what point should I just give up hope and move on?” Nine days and 23 hours ago. Sorry, for whatever reason, she’s not calling. ASH

I have been in the letter writer’s love interest’s position. I was playing in a band at a local dive bar, and met a woman after the show and got her number. Then I got caught up in work until I realized two weeks had gone by and I didn’t call. My band had another show three weeks after the previous one, and I figured I would see her there. Sure enough she was, and during set break I went up to her and said, “Hey, sorry I haven’t called, work got busy. I still have your number. Can I still call it?” She said yes. And I did. Been married 17 years since. JNEWCOMER27


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Column and comments are edited and reprinted from boston.com/loveletters. Send letters to meredith.goldstein@globe.com.