QUESTION: 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.