How Do I Make a Move on an Older Man for the First Time?

age_gap_dating_august20_13QUESTION: I just moved into my neigh­bor­hood a cou­ple months ago and I always see this gor­geous man at the gro­cery store around the corner—he’s clearly suc­cess­ful and looks like he could be a lit­tle older than me. We’ve exchanged glances a few times and he held the door open for me once, but other than that, we’ve had no inter­ac­tion. I’m so attracted to him and I really want to ini­ti­ate con­tact, but I have no idea how to. It’s easy pick­ing up col­lege guys, but I feel like I need a lit­tle more game with this suc­cess­ful man. How do I make a move?

CHELSEA SAYS: The first thing you have to do is make eye con­tact with the suc­cess­ful man. It’s always been the best way to show some­one that you’re inter­ested in dat­ing them. Don’t flash a forced, cheesy grin—that’s just awk­ward and a lit­tle creepy. Instead, just smile sub­tly while you hold his gaze for a cou­ple of sec­onds. If he looks away imme­di­ately, then he’s prob­a­bly not inter­ested. But if he smiles back, there’s a good chance you’ll be able to reel this man in. Once you’ve got his atten­tion, you need to ini­ti­ate con­ver­sa­tion. Here are a few tricks to get the ball rolling:

• Ask him for help—all men want to feel needed. Ask him to help you get some­thing off of a high shelf (but make sure he sees you try­ing on your tip toes first—that way he’ll know that you’re not fak­ing it). Or ask him to help you pick out some­thing. If he’s in the pro­duce sec­tion, ask him if he can help you pick out a ripe fruit, because you always seem to find the bad ones. The fool­proof way to make him feel like a man is to ask him to help you carry your gro­ceries out to your car. A gen­tle­man will never turn down a damsel in distress.

• Ask him for his opin­ion. Start by scop­ing out this suc­cess­ful man’s cart to see what kinds of things he’s buy­ing. Pre­tend like you’re hav­ing trou­ble decid­ing between two prod­ucts and then ask him which one he thinks you should go for. Again, this goes back to mak­ing him feel needed.

• Once you’ve sparked a con­ver­sa­tion, keep it going by ask­ing him ques­tions about him­self. Stick to the usual ice­break­ers. Try, “I’ve seen you here quite a few times now. Do you live in the area?” Men­tion that you’re new to the area and ask him for sug­ges­tions about other great spots in the neigh­bor­hood. That way you can throw in some­thing like, “Maybe we can check it out together sometime.”

Here are a few other things to keep in mind when try­ing to get your older man’s attention:

• Show him that you have com­mon inter­ests, which is impor­tant if he’s going to con­sider dat­ing you. If he’s brows­ing through the organic foods sec­tion, make sure your bas­ket isn’t filled with frozen din­ners and instant noodles.

• Don’t try to sound too smart. He can prob­a­bly tell that you’re younger than him, so don’t try to make your­self sound older than you really are. At the same time, don’t be a ditz. A dis­tin­guished, suc­cess­ful, mature man will not find that attrac­tive. As cliché as it sounds, the best thing you can do is just be yourself.

• Make sure you look hot. Don’t go gro­cery shop­ping in your ripped sweats and baggy T-shirt. I’m not say­ing pull out your lit­tle black dress, but throw­ing on a pair of fit­ted jeans, a nice top, and a pair of boots wouldn’t hurt. It shows him that you’ve got it together.

• Show off your assets, even at the gro­cery store. “Acci­den­tally” drop some­thing in front of him and don’t use your knees when you bend down to pick it up. He may be a suc­cess­ful man just shop­ping for gro­ceries, but he’s still a man.