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5 Questions You Must Ask On A First Date

First Date Jitters?

Ahhh, Cuffing Season. During the Fall and Winter months single people find themselves alone while the rest of the world is consumed with indoor activities including cuddling and binge-watching. So don’t be alarmed by the large amount of guys trying to ask you out, the explanation is simple: “winter is coming.”

So for that hot first date you have coming up, we are here to help with your anxiety.

The key to dating is to RELAX and avoid trying to “interrogate” the equally shaken person sitting on the other side of the table. But that doesn’t mean you should avoid getting to know this potential relationship prospect. So to get all the value –and for that matter save money and not result to online dating– we have come up with “The Three D’s”:

  • Be Diplomatic. By all means ask questions but no one wants to be treated like they are on a job interview. Don’t personalize them, or judge too harshly if you don’t get the answer you want.
  • Be Discreet. Basically be a good poker player. Make the conversation easy, and don’t force an issue.
  • Be Delicate. You’re not trying to solve a murder here; your trying to get to know your date in an informal, relaxing manner.


So what are the direct questions you should ask? Here is a good list that will reveal some key takeaways from that first encounter:

“Where did you grow up, and what was your family like?” This question is to see if they’ve had a “stable” upbringing. If they avoid the question they may be wrestling with some deeper issues but this doesn’t have to be a deal breaker, if they are working to grow from it. If they start reminiscing about childhood memories and telling childhood stories you could be on a good track.

“What  makes you laugh most?” A good sense of humor is on the top of most women’s list when is comes to looking for that special someone. But not everyone laughs at the same things. Some people laugh at humor that other people find rude. Some appreciate putdowns and sarcasm, while others want their humor clean and gentle.

“What’s your big passion?” Keep your ears open for this answer. If your date answers with the dreadful, ” I don’t know”, this could be a big RED FLAG. But I’m sure you will get a better answer because I believe in your choice of dates. Follow with question about why that’s their passion.

“What are you looking for in a relationship?” This shouldn’t be the first question out of your mouth, because this can be a tough one. This must be asked though, why waste your time with someone looking for a weekend fling if your looking for more.

“What do you like to do on the weekends?” If they work on their day off, they might be a workaholic. If he coaches a kids soccer team, this could be a good sign of him liking children. If he watches TV and plays video games, you may have a couch potato on your hands.

Go forth and conquer!


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Kiara Brown

The Creative Director of The G Spot Blog. I am first a blogger, second a stylist, and an equally an artist. Style On, Ki Brown @KiStyleMe

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