Many New York City single men have little problem getting first dates. Among their friends, co-workers, relatives, local bars, and online dating sites and apps, their New York City singles network is extensive. For a lot of single guys living in Manhattan or other New York City boroughs like Brooklyn, however, a second date is harder to come by, confusing them as to why. After all, if a woman agreed to a first date with them, why wouldn’t she want to go on a second date?

New York City single men often make the critical mistake believing that a first date is merely a time to allow women to get acquainted with them. They think, falsely, that they’re supposed to tell the woman they’re on a date with as much as possible about themselves so that the woman will want to go out again. Although that appears to be a practical strategy in theory, in reality, the results of communicating this way on a first date can be disappointing, leaving guys going on endless first dates that rarely lead to a second.

Single men in New York City who want to become better daters, find a meaningful relationship, and fall in love need to change their focal point while on a date. Instead of telling their dates everything about themselves, they need to spend more time learning about the women they’re dating. When a woman agrees to a first date, she is, in essence, giving that guy one shot to impress her. If he blows it, she’s likely gone forever. So he needs to make that shot count.

Although New York City single women are independent, they also want to know that the guy they’re with is in control of the date. His first step in creating a fun first date is to plan the date. Likely, he has already had a little time to communicate with the woman before their meeting. That means he should already have some idea about what she likes and, perhaps, doesn’t.

Thorough planning begins with picking the right spot for the date. The place you meet in and around New York City should be public, safe, pleasing to the eye, and quiet enough that you can hear each other speak. Pick a few options; the key is to take control but also act considerately, giving your date flexibility and choice. The good news is Manhattan, Brooklyn, and the rest of New York City’s boroughs have endless dating spots for fun first dates.

Once on your date, it’s crucial not only to ask the right questions but also to be a good listener. As tempting as it is to talk about you while on the date, your goal should likewise be to learn about her, including what she enjoys so you can plan a second date that will appeal to her. Talk about yourself but then ask questions about her. A good rule of thumb is to use your Ws: where, when, what, and why are only a few examples. A question such as “Where did you go to college?” makes an excellent jumping off point. Next, allow her to answer your question without cutting her off. After she has finished, jump in and tell her where you attended school, when you graduated, and what you studied while there. Give the conversation time to flow and see where it goes.

As you’re learning about each other, plan your second date by making mental notes about her specific interests. If she loves the opera, Broadway shows, small theatrical productions, or sporting events, consider making one of these your second date venue. A second date should be all about her and what she likes to do. But one caveat: don’t call it a second date. That can sound like a lot of pressure to some women.

Similarly, don’t ask the vague question whether she’d like to see you again. Rather, tell her you would like to invite her to a specific event. The phrases, “Hey, I’ve got two tickets for Saturday’s basketball game at MSG. Would you like to join me?” are quick and easy sentences that get your point across in a fun, upbeat way while putting little pressure on either of you as well as limit the risk of creating an embarrassing situation should she decline. Your invitation for a second date may be casual and light but subtly still lets her know you’re interested in her, a take charge kind of guy who’s willing to court, and, as a result, someone she’d like to go out with again.