15 Things You Shouldn’t Ask on a First Date, But Want To

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I don’t date strangers. I have come to realize this; for the most part every relationship that I’ve been in has blossomed from some level of friendship.

Now that I am in my thirties I am finding that my social circle is a lot smaller than it used to be and in turn, so is the dating pool that I have been accustomed to. Which is what brought me to the wonderful world of online dating – because approaching someone in public was completely out of the question, obviously. And the serious case of Resting B*tch face that I have going on does not help matters, at all. I can count on one hand the number of guys who have approached me in person and it’s normally to talk up my more smiley (and thus more approachable) friends. Whenever I go out I constantly hear someone whispering “smile more” in the back of my head.

So back to dating and meeting up for drinks or coffee or whatever noncommittal yet social activity that people do on ‘first dates’.

I recently had a guy (who I happen to work with) approach me and ask me out to dinner. (Yes, dinner! I was actually surprised as I’m not often asked to dinner, and actually the last time was with this guy.) The only thing is — I know nothing about him other than bits and pieces of information that I have picked up in passing, some of which were a bit concerning. There are things that I wish I could ask on a first date, things that I know are not necessarily “acceptable” to ask out right and can be somewhat personal in nature. The way I see it, these are things that may be important to ask up front and will help me determine if I want to proceed.


15 Things you want to ask on a first date, but probably shouldn’t

1. How much money do you make?
Come on, sometimes this is important, I need to know if you are looking for a sugar momma or a companion (hoping for the latter because I am tired of footing the bill all of the time).

2. What do “equal rights” mean to you?
This is definitely one of those things that can start trouble as people can feel really strongly about it.

ask on a first date

3. Have you ever been arrested or been to prison?
Should I be worried that you’ll…er, kill me or clear out my bank account?

4. Why did your last relationship really end?
AKA is there anything that I should really be paying attention to in case you are hiding something. Be your crazy self, at least then I will know up front what I am dealing with. No one likes when you bust out the crazy a couple of months in.

5. Do you believe in a higher power?
This kind of goes with question #2. I am not a religious person myself, but I am not going to hold it against you if you are, so long as you respect my views. Ya dig?

6. How do you feel about gun control?
Sometimes they are good and sometimes they are bad, but can we agree on those situations without getting mad at one another?

7. Do you have mommy/daddy issues?
Am I going to have to compete with the love and affection of your parent? Is your relationship with your mom a healthy “I’m not looking to date my mother” kind of relationship? If so then I think we are OK. I am NOT a replacement

ask on a first date

8. Republican, Democrat or Other?
Politics tends to be one of those things that people are not supposed to talk about, again, it is one of those topics that people can get really heated over. Basically, and this applies to most things of this nature, I need to know that you at least respect my views or we can agree to disagree and live in peace.

9. Have you ever been institutionalized?
Repeat: are you going to bust out the crazy or what? If so, I would like a little bit of a heads up on that, thanks!

10. Do you have any of your Exes on the back-burner?
I am not saving anyone’s spot in line, if you have not gotten over someone completely and are not ready to move forward then maybe we shouldn’t go on our date. I am looking for someone long term, not for right now, so I need to know that you are at least open to the idea of moving forward with some sort of commitment. I do not need you to come back to me months later saying the girl you REALLY love is back and wants a second chance. (Yes, it has happened before, more than I’d like to admit.)

11. Are you a sociopath?
Enough said, right? Your kind is a bit harder to pick out and I have fallen for your charm before. NO MORE!

12. Are you going to cheat on me?
Oh, you think monogamy is not human nature, then I think we will part ways here.

13. Are you married?
Obvious question right? You would be surprised how many people tend to forget this bit of information. And unless you have a copy of your signed divorce papers, I am not going to fall for the “We’re separated, but it’s complicated.” Or better yet “I love you, but I’ve made a mistake

ask on a first date

14. Are you going to get fat if we date?
Not everyone in my family is fit, so I am well aware of the fact that if I am not careful I can balloon and I try to take care of myself. Now I know that it is not always about genetics, but if I am going to try and ignore the insane “pregnant lady” cravings I get, then I would like to know that you will also do the same. Let’s keep each other in check, shall we? Either that, or we’ll balloon together, k?

15. Why are you really single?
Do I really need to explain why this is important but may not be something that is okay to talk about on the first date?

The list of things that can be asked is enormous, but I think if you asked everything you really wanted to know up front you would be sitting at the coffee shop for hours, if not days. Plus, even I will admit that sometimes it is more fun to find things out over a period of time. Some things are more important to know, but how can you possibly figure everything out in that first meeting?

Did I miss anything? Is there anything that you think is important to know up front but may not be socially acceptable to ask?

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Co-founder, Editor. My dating life can best be described as a lazy Sunday afternoon of window shopping.

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