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5 Things Men Don’t Want to hear about on a 1st Date by Top Dating Coach

awkward first date questions to avoid

Maybe these will surprise you.  Maybe not.   But as a top dating coach, half of my clients that I work with on a weekly basis are men---and the stories they tell me!  Before you think I’m singling out women, just a heads-up, the next article will be about things that drive women crazy when online dating, or dating in general.

So, what a first date meant to be?  Only a chance to see if you’d like a second date, not a therapy session.  It’s meant to be light, fun and see if you have a bit of chemistry and topics in common.

About 50% of men and women follow these “rules”.   But the other half, oh my!

So, let’s get on with what men never want to hear on the first date:

1.     Why the split up (got divorced) and in particular who initiated it. 

Think of it this way---you are at a dinner party or networking event, would you ever in a million years ask this question?  Hopefully, no.   Why do you care at this point?   Now, this can become much more relevant after 4-5 dates; but at this point, there is interest on both sides and you may have a brief chat about what occurred.  Big first date no-no and a 100% guarantee you won’t be seeing a 2nd date with this person.   Most of this will come out over time, so please don’t ask about it.


2.     Complaining about anything


“A negative attitude drains, a positive attitude energizes”.

Wow, this bodes well for happiness in the future, right?  Wrong!  Here are a few examples from this past week:


My client, Michael, 59, in NYC, met Lana for a lunch date on Tuesday.  She walked in 10 minutes late, complained about her Uber driver and how the rain had ruined her hair.   The date went downhill from there---she proceeded to tell him about her arrogant boss and that she was thinking of changing jobs/careers.  What were his thoughts?  He told me, “She will be a nightmare to be in a relationship with” and he’s one of the most positive guys I’ve had the pleasure of working with.   Even Lana’s good looks could not overcome her personality!

Ok, here’s another one for the books!  Tim, 48, my client in Boca Raton met Annaliese for a drink.  She immediately said she was famished and did he mind dinner too?  (Yes, he did as he just wanted to grab a drink and perhaps an app and go to his son’s soccer game after).  He voiced he had another commitment afterwards and guess what she said?  Well, then, I hope you are at least paying for this date as it took me over an hour to get ready.   Rude?  Yep.  By the way, men don’t care how long it took you to get ready.  No one cares!


3.     Physical Ailments

No, no, no!  You have upcoming dental surgery or just got over a bad flu.  Do you want to sound like a hypochondriac? 


4.     A political rant

Ohhhhkkk.  I won’t touch this with a 10-foot pole.  Isn’t our country divisive enough as it is?  Why would you want to start a fresh relationship and encounter with a person over this?   Yes, you may feel strongly about this and this is your right.   It just does not show you in the most positive light.  Remember, I didn’t say a gentle conversation about the USA’s state of affairs---I said a political rant!  You just come across angry and it’s not an appropriate conversation for a first meeting.


funny first date questions

5.     Problems with Children/Family relationship conflicts

I think we’ll just call this oversharing and inappropriate.   This happened to Steve on Monday (my 64-year-old client meeting Tanya for the first time).  She mentioned how upset she was that her 23-year-old daughter had cut her out of her life and then went on with why.  Steve just told me afterward “Thank God it was coffee and I was out of there in 30 minutes”.   He called me Friday afternoon to tell me about Karina---the antithesis of Tanya who was light and laughter and they made plans to play disk golf tomorrow and he was excited. (ohhhh, I'm excited to play disk golf too!!!)


Hey, we all have our ups and downs in life and I’m not saying you show up full of butterflies and rainbows. Isn’t that why we have best friends to talk through our issues or a therapist?  Think of your behavior on dates---don’t you want to put your best foot forward?  And, if you can’t do this, maybe hold off on dating until you can resolve some of your issues.


Happy Dating! BTW, I did laugh as I wrote some of this----and happily over 65% of my clients find their partner!


Andrea McGinty Founder and

Andrea McGinty

Founder, (sold)


Top dating coach featured on Oprah, Today Show, Wall Street Journal, New York Times, Kiplinger’s, People and more for helping singles navigate online dating, writing online dating profiles to dating advice.

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