First-Date Questions You Won’t Regret

Meeting someone for a first date can be simultaneously thrilling and nerve-wracking. Even if you’re acquainted with someone through work or a club, or maybe you’ve made a connection through a dating service, meeting in person for coffee or a drink with the explicit purpose of “dating” puts things in a whole new light. This could be the start of a deep and lasting relationship (hence the thrill), but you could also get so nervous that you’re at a loss for words or even just say something dumb.

This is such a common concern that Stephanie L. King, writing for Oprahdaily.com, found no shortage of relationship experts, sociologists and authors eager to share their advice on making a first date go smoothly. Their tips included the following:

“Start by trying to make a connection.” You probably met your date in some typical way — through an online dating service, for example, or by joining the same club.  It’s easy to ask a few questions about that connection. But things get interesting when you go beyond the easy connection. If someone introduced you to each other, talk about how you know that person, tell a story or two, then ask how they met your mutual friend.

“State the obvious.” It doesn’t get any more obvious than making a comment about where you’re meeting. But don’t just talk about how much you like the coffee shop — maybe you have an interesting comment about the neighborhood. Be creative.

“Don’t ask them what they do for a living.” Or, make that, don’t only ask what they do. You can explore that topic if you follow up with something like, Did you have to abandon any other interest that you might be sorry you didn’t pursue?

“Pay attention to how they respond to you.” You don’t have to be a psychoanalyst to figure out a bit about a person’s character. If they constantly turn the conversation to themselves, it may be a warning sign about an outsized ego.

“Ask them about their talents.” How a person talks about what they’re good at can reveal much about character. Are they thankful for God-given gifts? Do they describe how difficult it is to hone a craft, and how much they respect others who may excel in their work?

“Learn about their family and friends.” There’s no one-size-fits-all answer when it comes to friendships. There are, however, some reliable guides. If a person has several or many long-term friendships, it’s a pretty good sign. On the other hand, if a person is moving on after the breakup of a long-term relationship, many of the old friendships may have developed as couples. It may be, as they say, complicated. Listen to how they describe their relationships and whether they may take responsibility for any complications.

“Unpack their idea of a ‘good life.’ ” This is a wonderful way to get a good glimpse of a person’s value system. Do they focus on something like material success, or is it a more balanced outlook?

“Discuss favorite things.” Although this might be a rather light topic (and there’s nothing wrong with having some light conversation), it might also be an effective way to gauge your overall compatibility.

“Bring up travel.” This can be a surprisingly revealing question. If one of you has traveled extensively and is quite ready to enjoy the pleasures of home, and the other is dying to see the world at last, complications are in store for a long-term relationship.

“Address dealbreakers.” Speaking of complications that might affect a long-term relationship, surface compatibility — enjoying the same type of food or entertainment — pales in comparison to deeper issues. It may be crucially important to you that you share a value system in general and religious convictions in particular. This may not be a topic for a first date, but it certainly needs to be addressed if signs point to a long-term relationship developing.

Finally, remember to try and make the questions flow naturally. After all, it is a date — not an interview.