QUESTION: I really want to ask this younger woman out on a date—we go to the same gym. I know she’s single because she mentioned it in conversation once, but I have no idea if she’s into older men. I’m not even entirely sure how old she is, but she looks younger. Anyways, how do I go about it without coming across as a creepy old guy?
CHELSEA SAYS: The best way to not come across as a creepy old guy is to not act like a creepy old guy. Don’t ogle at her from a distance and then use cheesy pick-up lines to get her attention. It won’t work. Just be yourself!
It sounds like you and this younger woman have already had some conversations, somewhat in-depth ones too, if you know her relationship status. So, the next time you see her at the gym, approach her. Strike up a normal conversation and then casually ask if she’d like to grab a meal or something with you after your workout. And whatever you do, don’t age yourself while you’re talking to her. If you can tell she’s younger, she can probably tell that you’re older. Bringing extra attention to the age difference will just make it awkward and uncomfortable for both of you.
You’ll be able to gauge pretty quickly if this younger woman is into you. Don’t be offended if she turns you down. Not every woman is interested in dating older men, so try not to take it personally.
If you do end up going out on a date, keep it casual, just until you get a better sense of what she’s looking for.
TRENT SAYS: How about you just don’t be a creepy old guy? Gyms can be a great place to meet people. The good thing about meeting someone at the gym is you know you both share some common interests, like being physically fit and healthy. On top of that, most people that work out also tend to be confident and up for a challenge; the same qualities that are good in a relationship.
While people at the gym are primarily focused on working out and not focused on meeting other people, it sounds like you’ve already broken the ice; or I presume you have, since you’ve had the kind of conversation where she tells you her dating status. That doesn’t just come up in the first minute or two of casual banter.
As a side note, I’m not sure what your exchange with her was like, but she could have easily told you she was in a relationship, seeing someone casually, or working the circuit. But she didn’t.
I suggest you do exactly what you did when you had your first chat with her, but don’t talk endlessly about the gym—just because you met her there, it doesn’t mean you have to dwell on it. Ask her a couple questions that tell you a little bit about her day-to-day life, like if she’s seen a movie, read any books, or what her plans are for the holidays—these are always easy conversation starters.
If the moment presents itself, tell her you’d like to get to know more about her outside the gym some time. And if she’s open to the idea, you’d like to meet her for a bite to eat or something.
Thank her after you get her number, tell her you’ll call her in the next day or so, and leave her to continue working out. After all, you want to intrigue her, not be the no-neck guy who stalks her once you’ve made a connection.