1.  Don’t Cross-Examine

Listening is one thing (and a really attractive thing – guys often complain that women talk about themselves too much, on dates and in relationships). Intense questioning, however, can be intrusive and can give your date the impression that you have a set of standards in your mind and you’re trying to see if he passes them.

2.  Don’t Judge Based on How Much Money He Spends (or Has)

As a rule, guys are very sensitive about how much money they have (or don’t have). They will often expect that you’re paying a lot of attention to how fancy or expensive the date is, and will worry you think it’s a reflection of their resources. So make sure to be effusive about the venue, etc., and about how much fun you are having. (If you liked the guy, but are disappointed because the date wasn’t fancy enough and/or are exclusively looking for a guy with a lot of resources, you have other problems on your hands).

3.  Don’t Brag 

MENSA member? Former Miss Alabama? Don’t share this information on the first date, even if it is relevant to the conversation. It makes you look insecure.

4. Don’t Criticize How He Decorates His Apartment

Many guys who live in apartments that look like college dorm rooms think they are feng shui experts. If you must, try some constructive criticism. (“Wow, I love the color of your couch! It would be so cool if your kitchen table was the same color.”) 

5.  Don’t Play Shrink

Don’t ask about his relationship with his mother, etc. If the relationship progresses, that information will come to you organically. At this point, ask friendly, curious questions and listen carefully to his answers. If you ask him a question about his job and he says he likes his job, ask more questions about it; if he doesn’t seem enthusiastic about it, ask him how long he’s had fishing as a hobby and how he first got interested in it. 

6.  Don’t Talk About Previous Bad Breakups

Talk about past relationships is standard first-date fare. After all, both of you are likely nervous. But, don’t talk about conquests or bad breakups. Instead, talk about “successful” breakups: i.e., breakups in which you’ve maintained friendships with exes.

7.  Don’t Let Him Pick Up the Check

Always offer to pick up the check. At the very least, offer to split it. This is an ironclad rule that guides independent of whether you would like to be treated on future dates, how much money the guy makes or has, how much fun you had on the date, and whether you’d like another date. Some guys wouldn’t dream of letting a lady pay her own way on a date, let alone pay the entire bill, and many will refuse. But some will accept, sometimes for understandable reasons, and almost all guys will find the offer quite charming.

Justine Borer is a family and matrimonial lawyer practicing in New York City. In her spare time, she loves to write, act, do pilates, and spend time with family and friends.
One Comment
  1. Seven is the most ridiculous stupid thing that you could do with a man on a date. A date is a date, and a man needs to be a man and it doesn’t go 50/50- including paying for a dinner. A man should be pursuing a woman and it would be impolite and downright rude any other which way. Your advice should be kept in your own closet!

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