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QUESTIONS TO ASK ON A FIRST DATE
IN MILWAUKEE…OR ELSEWHERE

 

I get it. We are nervous, curious, excitable human beings.  And when there’s that deadly silence, it’s human nature to want to fill the void with chatter. But not all thoughts need to be verbalized. Just like on a job interview, when that silence happens, (which it will), best to take a deep breath, look out the window and continue on. Remember, you can’t take words back, and unless you are a yoga master, it's difficult to get your foot out of your mouth.

 

So, what are acceptable questions on first dates?

 

  • Tell me about your family? (do you have siblings—are your folks still with us?) Where did you grow up and what was one of the most memorable moments of your childhood?

 

  • Where/when was your last vacation? What was a highlight of that time—and would you go back if you had the opportunity? Where else is on your bucket list? (Travel questions are wonderful to ask because generally, people love to talk about their vacation experiences, their mishaps and so on.

 

  • If you could have someone over for coffee—who would that person be, and why?

 

  • Tell me about the happiest moment of your life. If the person sitting across from you has had children, undoubtedly they will say “when my son/daughter was born.” Ask them—what did that feel like?

 

  • If you won a million dollars, what would you do with the money?

 

  • Tell me something about yourself that I wouldn’t think to ask you.

 

  • (My personal favorite!) What would your parole officer tell me about you that I wouldn’t think to ask!

 

  • (And to get really silly….) What is a moment in time that was a missed opportunity for you?

 

Remember, avoid ultra-personal questions about money, religion, politics, sex, and ex-husbands or ex-wives. These are off limits until you both feel comfortable about discussing them. Many times I’ve wanted to ask for the ex-wife’s  phone number to get an idea of what to expect, but obviously, it’s totally inappropriate. Enjoy, have fun and at the very least, the date will offer practice for you for when your true dreamboat comes along.

 

Lori Mendelsohn connects people both personally and professionally. With a knack for introducing people who wind up saying, "I do," she can of course be reached by email..

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