DEAR DR. NERDLOVE: I have been hanging out with this girl 7 times now with her doing the majority of the asking not me. She has canceled meet ups before quite a bit so it could have be more than 7 times if other hangs weren’t canceled. She had also brought up future plans to hang out quite often also.
On these hangouts there has been no flirting or physical touch or signs to make a move on her. Basically no initiation from either of us. This girl is 37 and I’m 45.
What do I do with this girl?
Going Nowhere Fast
DEAR GOING NOWHERE FAST: Alright so I have to say this right off the bat: you really don’t want to refer to a grown-ass adult woman as “girl”. She’s 37, not 16, she’s a woman, not a girl. While I’m sure that’s not your intent, calling her “girl” is patronizing at best and a little insulting at worst. Do yourself a favor and start working on breaking that habit; trust me, it’ll spare you a lot of unnecessary grief in the future from folks who aren’t going to be generous about your intent here.
Now with that out of the way: I think the bigger question here is “what do you want out of this relationship?” There’re two people involved here, and neither of you have made a move to take things in a more physical or romantic direction. Since you’re the person writing in, you’re the only one who can really answer the question of “what’s going on in your head over this?”
I think we can say with a degree of certainty that she likes spending time with you. After all, you’ve hung out multiple times – 7 at least, and more planned in the future. She’s been initiating a lot of the plans you’ve had, so clearly she’s either getting or hoping to get something out of this. Maybe she’s digging you as a platonic friend, or maybe she’s been waiting for you to give her the sign that you’d like to take things up a notch. You don’t say whether you are interested in seeing her as much as she seems to be in seeing you; are you not making plans because she tends to bring them up first? Or are you just going with the flow and waiting to see?
So the first step is simple: are you happy with how things are going? Are you hoping that this is going to lead to some kind of relationship beyond the platonic? If the answer to the first question is that you want more, then the second question becomes: why haven’t you made a move to escalate things?
This isn’t an idle question. It’s one that really deserves some consideration. If it’s a case that you’re kind of “meh” about her as a potential romantic or sexual partner, but not as a friend, then continuing on will likely continue the status quo. Because you’re not giving her more signs that you like her as more than a friend, the odds that she will be the one to escalate are relatively low. If anything, the odds that she may get frustrated (if she’s looking for more than friendship) and break things off grow the more times you see each other without anything happening.
If you’re just not feeling it in general, either as a potential partner or as a friend, then all you’re doing is wasting her time – time that she could be spending either finding someone who is interested in her or time with that person. I’d strongly recommend just saying “hey, I’m not feeling it, best of luck to you” and ending things quickly and as cleanly as possible. It’s going to be messy – this has been weeks of her time and an investment of energy into you after all – but it’s still kinder to just do it in one quick move. The clean break heals the fastest after all.
If you’re interested in her as more than friends, then someone’s going to have to make a move to escalate the situation and that may as well be you. As I’ve said before: women get just as nervous, wondering if their dates and crushes like them as much as they like their dates and crushes, and are just as afraid of getting rejected as men are. By the same token, men are socially rewarded for being more aggressive in progressing a courtship in the early stages, while women are frequently punished, socially, for doing so, so your being the one to make the first move to level things up poses less risk. So if you’re interested in more with her, then the best thing you can do is to start acting like a potential lover instead of a friend.
Now, there’s a potential third thing happening here that would affect how you might want to progress things: she’s interested in you, but she may demisexual or asexual. That is: she may not necessarily feel overt sexual desire until she feels more connected to you emotionally or she may not feel much sexual desire at all.
This is why I would recommend saying something rather than just going for a kiss. Adding some flirting into the mix when you hang out the next time is a good start and a way of signaling that you like her as more than a platonic friend. If she responds positively, then I would recommend picking a particularly romantic or charged moment, look her in the eye and say “I’ve been unsure about how to do this, but I really want to kiss you right now.” Then give her a moment to either give you the green light or wave you off. If she gives you a positive response, cup her cheek very lightly and lean in to kiss her. If she gives you the wave-off, then take it with good grace. Don’t immediately assume that this means that she’s not interested; she might be surprised, might need a minute to process things or may need to decide if she’s ok with being kissed. Give her the room she needs and let her tell you how she feels. Don’t try to kiss her again until she gives you the green light.
If she’s not interested in you romantically or sexually… well, now you have to decide if there’s enough there that you would like to be friends with her. If the answer is no, then again, I recommend breaking it off as quickly and cleanly as possible. If yes… well, carry on as you two have been. No need to change something that’s been working so far.
But as I’m always saying: if you want things to be different, you have to do things differently. Someone’s going to have to take decisive action to break the status quo and since you’re the one writing in, you’re the one who’s functionally stepped up to the plate. Time to make your move, one way or another.
Good luck.
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Please send your questions to Dr. NerdLove at his website (www.doctornerdlove.com/contact); or to his email, doc@doctornerdlove.com