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5 first-date questions to avoid

Photo of unhappy couple on date

And clients share them with me.  All the time.  For 27 years as a dating coach.  But this week I got an earful. 


And I work with intelligent people.  Successful.  But often the questions you ask on dates, I’m flabbergasted.  


Maybe it’s something in the air this week.  Summer is right around the corner and a super busy time to date.   And I’ve been super busy too which increased the number of phone calls with clients, reviews of your texts with potential dates…and your date conversations.  


Then, you wonder why there’s no second date.  Men.  Women.  I work with both of you….and you both do it!


Things I pray I never hear again from a first date:


  1.   How long have you been on the dating apps?


Why it’s problematic: It implies judgment and makes the date feel like a seasoned "dater," potentially creating discomfort or defensiveness.


Who cares?   Why would you care?   Especially on a first date.  It matters because …..why?   How on earth does this affect whether you go on a second or third date or marry him/her?


I have so many examples but I’ll go with this one:  Lara, 58*, Palm Beach Florida.  Spunky, funny, athletic and pretty.  We are looking through men online together (by phone), and by the 4th time I’ve picked a high potential date for her—-she says the same thing for the 4th time “No, I’ve seen him online for the past 6 years.  He’s a player”.


Ok, I’m direct.  Very direct but graciously direct as my only interest is you ending up in my 65% success column of clients who are in long-term relationships.   


Me: “Lara, and you know he’s a player how?  And you’ve been online how long?’


Lara: “That’s different.   I’m picky”


Me: “I bet he is too.   I read his profile.  He seems lovely.   I want you to give him a try and by next week when we have our coaching call I can’t wait to hear about your date”


Reluctantly, she did.   Reached out.  Date scheduled.  Turnes out to be an interesting and kind man.   He’d been traveling quite a bit with work and getting three kids settled in colleges and internships as a single dad the last 4 years with not much time to look at his online dating app.   He told Lena he was grateful she’d reached out.   Fingers crossed Date 2 goes as well.  


2.  How do you like Match, Bumble, Hinge, etc. {whatever app they are on) so far?


Why it’s problematic: It shifts the focus to the app rather than the person, often leading to negative rants.


Nobody likes a Dating App until they meet someone…. then it’s the greatest site in the world.



3.      What are you looking for?


Why it’s problematic: It’s too direct and makes the date feel like a job interview, putting unnecessary pressure on them.


If you are unlucky and get this question, cut it off quickly with this: ‘A second date with someone I like”.     Then change the topic and move on to getting to know each other——books, film, music, activities, current events.



4.      Why did your last relationship end?  Do you have a good relationship with your ex?


Why it’s problematic: It’s too personal and can bring up negative emotions or stories, which is not conducive to a positive first-date atmosphere.


After all, a first date is nothing more than a precursor to a second date, then hopefully a third date…and so on and so on.   Yes, it will come up naturally in time but this is not the time.


5.     Tell me about yourself….


Why it’s problematic: It’s vague and can make the date feel awkward, like they need to deliver a monologue or résumé.


By the way, a client of mine got this question and she began with: “I was born at 6:04 PM on Tuesday, May 9, 1971 at St. Lukes Hospital in Philadelphia…. shall I go on?”   


Her date started laughing and said, sorry, that was a stupid question.  The date just got better.  Ice broken.


Suggested Better Questions:

  1. You had great photos—where did you take the one scuba-diving?

  • Why it’s good: It shows interest in their hobbies and experiences, leading to a potentially engaging story.

  1. Where are you from?

  • Why it’s good: It’s a simple, open-ended question that can lead to discussions about background, culture, and upbringing.

  1. What’s the best concert you’ve gone to? Favorite films? Books?

  • Why it’s good: These questions delve into personal interests and can reveal shared passions, making the conversation more lively and enjoyable.

Additional Tips:

  • Keep it light and fun: The goal of the first date is to enjoy each other’s company and see if there’s chemistry.

  • Active listening: Show genuine interest in their responses rather than planning your next question.

  • Shared experiences: Discussing activities, music, or books can lead to discovering mutual interests, which is great for building a connection.

By focusing on these types of questions, you and your dates can promote a more positive, engaging, and enjoyable first-date experience.  And, hopefully, a second date and more!


*Name changed and location



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