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Why To Ask Personal Questions On Your First Date

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Many people advise to keep first dates light and carefree. This means not asking any “personal” questions, including about religion or politics.  As a couples therapist, I believe exactly the opposite, as you might be able to tell from listening to my podcast about whether you should say you like sex in your dating profile. After seeing how many couples split up because of basic incompatibility, I think: Why not see if compatibility is present sooner than later?  

When I was single and dating in DC in grad school, I heard the advice not to ask about people’s work because “people are more than their jobs,” and lately I have heard a resurgence of this advice, which my clients report receiving.  I strongly disagree with this because it violates this general axiom:

ASK ABOUT ANYTHING THAT IS DEEPLY IMPORTANT TO YOU!

Personally, my career is very important to me, and there would be no way for anyone to gain a full understanding of me as a person without knowing what I was in grad school for.  Since this was important to me, I was mostly compatible with people who felt the same way.  Asking about career was something that I did almost immediately upon meeting anyone, and it never went poorly.

This is similar for anyone who is religious, or political, or extremely interested in health/fitness, or anything else.  If you are dating with an eye toward finding someone compatible, then it is never too early to figure out if you are on the same page.  However, if you have too long a list of specifications, as I discuss here, that might indicate that you have some more growth and introspection to do before trying to find a long-term partner. 

When people have too many dealbreakers, this usually indicates a deep distrust of people and relationships, and is a way to avoid intimacy and connection.  Often, people with avoidant attachment are like this.  Because they fear intimacy and closeness, they come up with reasons why no prospective partner is exactly right for them, therefore protecting them against the pain they think would come from opening up to someone and possibly being rejected.

Another reason why you should ask whatever you want on a first date is that it is likely a genuine core part of who you are to be curious and want to know someone on a deep level.  Authenticity is an essential part of healthy dating, and as a couples therapist, I see way too many couples who were never completely open and honest with each other.  From the first date to the twentieth year of marriage, they were trying to come off as something different than what they actually are.  Here’s some examples:

  • A man acted like “a gentleman” while dating his now-wife, never telling her how much he valued physical intimacy and acting content with less sex than he really wanted.  This turns into a husband of 20 years who is incredibly resentful and depressed because he never had the sex life he wanted.
  • A woman acted super independent and “fun” while dating her now-husband, meaning that she never conveyed how much it bothered her when he prioritized friends and work over her.  Now she wants a divorce because he still prioritizes work.
  • A woman pretends she is okay with being the breadwinner and having her husband be a stay at home dad, because she feels she would be a bad feminist if she said otherwise.  However, this was never true, and now she is resentful over not being able to stay home with their baby.
  • A man never told his wife how deeply he valued raising children with the religion he was brought up with, because she looked down on religion.  Now, they have tremendous fights over the role that religion should play in their kids’ lives.

It may be obvious to you what the commonality is in these hypothetical examples.  The person wanted to avoid the short-term pain of potential rejection, so they pretended to have different values than they did.  This is how people with preoccupied attachment act in early dating stages.  They are so scared of a partner not liking them that they twist themselves into knots to be “lovable” by denying core parts of themselves.  This could be prevented by openly discussing who you are and what you’re looking for up front, from the first date onwards.

Should you ask about exes on the first date?  I think so, at least asking whether their divorce was amicable. If someone badmouths their ex-spouse, this is a huge red flag, as I discuss here.  In general, as the relationship goes on, I also think that it is important to talk about exes, but that is in order to deepen your connection and understand one another better.  On the first date, the “personal” questions should be aimed more toward assessing potential compatibility, not necessarily getting into details about the past.

If you are dating in order to find a long term partner, in my mind it is never too soon to ask about basic areas of compatibility.  It is also never too soon to share what is deeply meaningful to you.  As long as you don’t have an extensive list of dealbreakers, in which case it would be useful to explore why you are putting up so many guards against potential closeness, it is honest, open, and smart to convey to your date what makes you tick.  Happy dating everyone!  And till we meet again, I remain, The Blogapist Who Says, OkCupid, Where I Met My Husband, Gives You A Quiz About Values And Preferences!  We Were 92% Compatible.


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