Online Dating Tip: How to Flirt

10 dating questions to get sparks flying

By Liz H. Kelly Updated: Oct 14, 2008


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What can you say in an email or instant message (IM) to entice someone to get to coffee talk? You are trying to get to the first date level. So what are the tricks to flirting online?

Three keys to online flirting success:

1. Humor is your ally. A 35-year-old male film editor told me, “It depends on the person. You need to be able to read the person to tell what kind of humor you can get away with.

“Humor is definitely sexy”

Humor is definitely sexy, and so is confidence because girls pick that up.”

2. Keep it simple. Use light-hearted emails or IMs with an upbeat tone to attract dates online. A 40-something female painter shared, “Make your responses simple and use easy questions in your messages to flirt.” There is no need for long emails or IMs either. A 42-year-old accountant told me, “I can tell if I am interested in three or four sentences.”

3. Hand out compliments. One of the best ways to flirt online is to extend a sincere compliment. One guy told me, “I always try to say something subtle but sincere.” You might say to someone who plays the piano, “I think it is awesome that you play piano.” He added, “Be sincere and don’t throw out phony baloney.”

10 IM or email flirting questions


Based on interviews with hundreds of active daters for my book, “SMART Man Hunting,” here are 10 proven questions that can help you ignite sparks online:

  1. Where did you get that fantastic smile?

  2. What is your favorite ice cream flavor and why?

  3. What is the most romantic place that you’ve been on a date?

  4. What would you do if we got stuck in a snow storm in the mountains?

  5. If you were going to take me out for a romantic evening, what would we do?

  6. What is your favorite thing to do with a partner for fun?

  7. If you could go anywhere in the world, where would you go and why?

  8. How long have you played guitar? (Ask about something in their profile.)

  9. Wow, is that your cute golden retriever? (Compliment something in their photograph.)

  10. When are we going to meet to find out whether we would ever want to kiss each other? (Depending on the person, you can sound cute using this one)

Have some fun — use humor and good will. Keep it simple when you’re using these email flirting questions. You will have better luck using levity and sincere compliments online.

Liz H. Kelly is a dating coach and author of “SMART Man Hunting: The Fast Track Dating Guide for Finding Mr. Right (or Ms. Right).” Her proactive dating strategy has been featured on such shows as FOX News, BBC Radio, Dick Clark’s “The Other Half” and Lifetime’s “Speaking of Women’s Health.” Her dating tips have also appeared in Cosmopolitan, Glamour, USA Today and the Chicago Tribune. Liz is online at

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