Questions To Ask if You’re New to Dating

Question: Dear Luise: I am new to dating, as I am recently divorced. Can you give me some questions to ask a date to help me determine if they are sincere and are truly who they say they are? If I had some solid dating questions it would help me feel more secure about dating again, knowing I am asking the right questions to help me get to know someone. Some ice-breaker questions would also be appreciated…so I don’t sound like I am going out on an interview! (Ha-ha!) Thank you so much, Elise

Answer: Dear Elise: I would suggest you ask yourself some questions first. Asking questions is a great idea when you use yourself as a starting point. For instance: Can I trust the way I met this guy? What kind of an answer do you get? It is so much safer, (although not fool-proof, of course), to have a mutual friend that respects and protects you put you in touch with someone new.

Picking someone up whether at a bar or online puts you at a decided disadvantage. That’s because any questions you ask can be easily answered with misinformation, (a nice word for lies.) There is also that sneaky concept of omission…for instance, when a man forgets he has a wife.

A good question to ask a new friend is what groups he is associated with. You can often find out a lot about someone by getting him to talk about his own interests. It’s a path to possible mutual interests, too, and if he doesn’t ask you the same question in return, be wary of that. Both of you need to be interesting and interested to find a balance. Any conversation that is ego-lopsided is a red flag.

Having him take you along when he is with a favorite group, if that is appropriate, is another way to ask silent questions through observation. What kind of people does he hang out with? How do they interact? What is their attitude toward you? Also ask questions about his family, another vitally important group.

Of course all of this has to be done in a sensitive way and hopefully over time…so you avoid what you mentioned in your question, which is the feeling that you are interviewing an applicant for a job. In a way, that’s just what you are doing when you consider a new friend. The other person is doing the same thing but we all need to be subtle.

The last thing I would like to mention is that you simply can’t have a formula for asking questions. Everyone you date is going to be different and so the questions for couples to ask each other have to fit the person, the time and the place. Some people are very responsive and one question, asked respectfully, can activate a lively conversation. Then there are the “yup” and “nope” guys who make you want to tear your hair out. They will usually open up in their own way, if you’re patient, and it may worth the wait. Blessings, Luise

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