Our first message from this fellow was a sarcastic, “What would your advice be for me, being 40, bald, a minority, and despite being ‘a great guy,’ having trouble finding someone I genuinely connect with?” Were we talking to Montel Williams? The angry ghost of Gandhi?
He then wrote back to clarify, telling us the story of a date that ended in “let’s be friends,” which was OK because he didn’t feel much either. They hung out again, and despite not anticipating much, he “had a blast with her. I mean a really great time. Probably one of the best times I can ever remember having with someone in years. I felt that connection. But I parted ways without making any kind of overture.” They did yoga together, she suggested they try it again, they had another blast, and now he’s confused. “Here’s someone I feel a strong connection with, but the parameters are friendship. Do I want more? Yes. Would I be happy being her friends as well? Absolutely. Friends like that don’t come often, but I don’t want to wimp out of the opportunity of a lifetime. Do I tell her what I really think or just try to enjoy her friendship?”
OK, 40 is not that old. And you are a good looking 40. The baldness is pretty much a non-issue. I saw some pics on your OKCupid and know wherefore I speak. So stop stressing out.
In this situation with the cool crush/lady friend, you should go ahead and keep hanging out as friends for now. Give yourself a limit of, say, two months. When you’ve gotten to know each other better you’ll know if you really have feelings for this woman, or if it was just a passing fancy. The added benefit of time is that, usually, if you are a thoughtful sensitive person with no latent Aspergers, you can tell when chemistry is really real and you’ll be able to better judge if she is finding herself attracted to you despite her original protestations. At the end of two months, if you’re still into her and she seems like she might be into you, let her know how you feel. When and if you do, point out all your awesome qualities, which she should now know all about, and how much fun you guys have together.
If she says yes, pan to fireplace. If she turns you down again, tell her you understand, that you want to take a month off, and that you’ll look forward to hanging out again as friends when you’ve had time to get over it. Don’t bring it up again after that. Good luck!
Uh oh. Sally and I might need some relationship advice after this one, because, for the first time, we wholeheartedly disagree about everything. I’ll have the world know that Sally is sick with bronchitis and a sinus infection, and that she has been prescribed codeine cough syrup, which may be affecting her judgment (even though she hasn’t taken it yet).
Look, you know pretty early on whether you want to bed someone, be friends with them, or develop a romantic relationship. Despite everything told in rom-com movies, one rarely wavers from his or her initial assessment of a person’s fuck, marry, or friend potential. It seems like your response to this woman was slightly delayed, in that you didn’t feel a connection on your first date, but you did develop an attraction to her pretty early on. That desire for sex and a relationship is not going to go away if you’re friends, and she’s probably already decided for herself too.
Her initial response was “Let’s be friends,” and it seems she meant it. It’s likely she still feels the same, but check in about where you stand while the relationship is new. Tell her that you need to clear the air and say just what you said to us. “I didn’t go into this expecting much more than friendship, but I was pleasantly surprised to feel attracted to you as more than a friend. If you think there’s any romantic potential between us, let’s talk about it more.” (That’s where you kiss her if she says yes.) “If there’s no hope of romance between us, let’s get that out of the way now and focus on being friends because I think we have a real connection there.”
If all goes horribly wrong–which it won’t unless you say something offensive or make her feel really uncomfortable–all you’ve lost is someone you hung out with a few times. Most likely, you’ll keep her as a friend or wind up in a relationship. If you wait months, pining for what you can’t have until the feeling becomes unbearable, you risk a lot more. She may feel truly betrayed if she values your friendship but isn’t into you romantically and feels that you’ve been misleading her. You, in turn, may feel deeply hurt and rejected months in. Find out now.
At least we don’t disagree completely. Sally and David both think you need to make your feelings and intentions clear. She says to wait a few months. He says to do it now. Whichever advice you choose, don’t keep mum for long. Letting the feelings fester forever will make you feel too passive, undermine your friendship, and forestall romance (if that’s a possibility).