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As many of us are using online dating apps it’s difficult to know what to ask and more importantly what NOT to ask when you are first getting to know someone.

I personally have a very direct approach-I want to get to the good stuff right away and not waste any time. Some people find this a bit unnerving-many enjoy it. So, based on my uncanny ability to off-put easily, here are some recommendations on questions to ask:

  1. What is something you are most proud of? Let’s face it, everyone loves to brag. Give this potential new friend an opportunity to do so!
  2. What was your most favorite vacation and what made it so? I find that if men don’t go on vacations or haven’t left local soil, it’s an automatic deal-breaker. (That’s just me.)
  3. Where did you go to school and what made you decide your major?
  4. What is an organization that you volunteer with? (For me, again, this is important. Something that I look for, personally, is someone who is involved in his community and giving back.)
  5. What are some of your interests? (It’s been proven that couples aren’t necessarily compatible if they enjoy doing the exact same things, but rather, they can teach a partner something new)

You’ll be able to gauge the conversation accordingly by what the answers are. Also, when you are doing this check for spelling and punctuation. There are many scammers out there who are people who are trying to pull one over on you. Make sure you don’t fall for it. And always remember, have a great time-dating should be FUN!

Lori Mendelsohn

Lori Mendelsohn is a professional matchmaker. With a knack for introducing people who wind up saying, “I do,” she can be reached at Her website is