Gauge whether the man is interested in you. You’re taking a leap of faith and possibly attempting to overcome some feelings of intimidation because he is slightly older than you. It makes sense, therefore, that your approach would be easier if you knew he was interested in you. Try to spend time with him and do a bit of flirting, such as gently touching his arm, leaning forward toward him when seated and holding a smile for slightly longer than you have in the past. If he responds by flirting back, he’s probably interested.

Ask him how he feels about people of different ages dating. When you and the guy you like are in the midst of a casual conversation, ask him about his views on age differences. Avoid pointing out your age difference, which can affect his response once he realizes that you are suggesting a date. Instead, keep the conversation lighthearted and wait until you are already in the midst of a discussion before asking. If you two are out with friends or co-workers, ask everyone what their views are, so that he doesn’t feel like it’s an interrogation. Be sure to interject your views on age differences in dating, to provide him with information that might make your approach less stress-inducing.

Invite him to join you in an age-appropriate activity. You and your friends, who are also likely younger than the guy you like, may enjoy activities that he outgrew a few years ago. While those activities may still be fun for you, keep the age of the guy you like in mind when asking him out. Choosing an age-neutral activity, such as going out to lunch or dinner, is a good way to get the date going. If you’d rather ask him to a movie, choose one that appeals to an audience with a wide age range. If you’re unsure what activity would fit his interest and preference, it’s perfectly acceptable to ask him directly for suggestions, but don’t expect him to make the decision. If you’ve asked him out, it’s generally expected that you will determine what you will do on the date.

Suggest that he join you for a group outing, after work, on the weekend or in the evening. The slightly older guy may feel a little out of place going out initially on a one-on-one date with you. Consider softening the blow by asking him to join you with friends or co-workers, which can also take some of the attention off him. For added help in making him feel comfortable, ask some of his friends to join your group. This gives you both the chance to see each another interact with the people who are in your immediate social circles.