How Does an Older Guy Get a Date with a Younger Woman without Scaring Her Off?

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.