Top Questions To Ask On A First Date

Managing the dynamics of the first date is an important skill.

And, it takes practice. Especially for those who are dating again after a long-term relationship ended.

Be patient with yourself, especially if you haven’t done this in many years.

The first step is of course, to snag that first date.

One of the goals of my book was to help you achieve a great dating life in less time, requiring less trial and error.  With all the information and research contained in Getting Back On Top, my hope is that you will need far fewer dates to hone your skills than I needed when I first started dating after my divorce.

That being said, it is a good idea to be prepared for your first date. Part of that is having in your pocket some good questions to ask of your date– questions that will help you get to know them, which, in turn, will help you decide whether you should take it to a second date.

Of course you don’t want the date to seem like an interview, so use these questions sparingly. Some are more intended for “internal questions” you ask yourself about your date, to get in touch with your feelings about them and also becoming a closer observer of their behavior.

Here are some top first-date issues and questions that will help you decide whether you want a second date:

  • Does he/she want kids?
  • Does he/she have kids and how old are they?
  • What is his/her custody arrangement? (Gives you an idea of his/her availability and flexibility.)
  • Does he/she like to travel?
  • Does he/she communicate and express well?
  • Did he/she pick up on your innuendos and double entendres and how did he/she react to them?
  • How traumatic was his/her divorce and what were the reasons for the divorce? In that description, is there a concession that it was not all the ex’s fault? (It is never completely one sided, so a recognition of his/her part in the divorce shows perspective and humility.)
  • Is he/she cordial with his/her ex? (Beware the nightmare ex scenario.)
  • How long was the marriage or other serious relationship? (Gives you an idea of his/her staying power and commitment ability.) By the way, three or more marriages is a big red flag!
  • Do you feel comfortable with his/her eye contact?
  • What does she/he do professionally? (Gives you an idea of her/his schedule and availability as well as her/his need for intellectual challenge.)
  • What does he/she do in his/her free time? Sports? Arts? Hiking? Reading? Music?
  • Does he/she like to eat? What does he/she like to eat? Is he/she a foodie?
  • Is he/she a morning or an evening person?
  • What about lifestyle, vacation, days off? This is an often overlooked question but is one of the most important. If you are a traveler and like spontaneous activities, you will be very frustrated with a partner who has a conventional 9 to 5 job with two weeks’ vacation.
  • What is your date’s relationship to her/his father and mother and siblings? For men, their relationship with their mothers is key, and vice versa for women. This is critical. Not that a problematic parental relationship can’t be overcome, but it is a major hurdle. Much better to be with someone who has a great, loving, and communicative relationship with both parents but especially with the key opposite-sex parent. Delve into this deeply. Find out what that relationship is like and was like growing up, whether the parents were supportive of his/her marriage (if there was one), and whether they liked your date’s spouse, and how often he/she sees and talks to them.

Though not quite as important as the parents, your date’s relationships with siblings is worthy of a few questions. Find out how many there are and what sex and their birth order and how close they are to each other. Find out about the depth and frequency of their contact.

Your date’s relationships to parents and siblings will give you important insight into your date’s ability and willingness to maintain long-term and close relationships even when they are not easy to maintain. It will also give you an indication of the modeling and example that your date had while growing up–all important indicators for you to consider.

All this may seem like a lot to address on your first date, which usually lasts anywhere from 45 minutes to an hour and a half, but as you develop your skill, you will find it happens quite naturally.

Give these a try!