12 Things You Should Never Say on a First Date

Updated 10/23/17

Being single for the better part of the past decade, I mastered the art of first dates long ago, and I actually enjoy going on a date with a man I hardly know. In fact, I’m a little embarrassed to admit that I’ve been on an insane amount of first dates—quite possibly in the hundreds—and while I can’t remember them all, I do recall quite a few, both good and bad. I love first dates because they are filled with anticipation (it’s exciting: the possibility of meeting your match!) and, if you’re lucky, fun.

However, when you are on one of those amazing first dates, after a couple of glasses of Sauvignon Blanc, it’s easy to let your guard down and reveal too much. You don’t want to scare away your new love interest by saying the wrong thing. So what topics are off-limits? Here are 12 things (from my personal experience) you should never say on a first date.

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1. What happened in your last relationship?

On the first date, you’re just getting to know the person, so you don’t need to know why the last relationship ended in shambles. Save this question for further down the line. Instead, ask about their childhood, where they went to college, who their favorite baseball player is, and what their preferred part of the Thanksgiving meal is.

2. I’ll pay.
I’m old-fashioned and like it when a guy pays for the first date. While some people believe it’s important to pretend to want to pay by doing something absurd like reaching for your wallet, this is not a good idea. What if he says, “Sure, you pay”? Will you resent him for it later? Don’t play silly games. If you want him to pay and he is willing to, then let him. Be sure to express your heartfelt thanks afterward.
3. I just have to make a quick phone call. Do you mind?

After meeting someone new for the first time, you’re going to step away to talk to someone else?

Not cool. Keep your phone in your purse. Even resist the urge to pull it out to share those photos of your adorable new puppy; you may see a text or call from someone and be unable to not respond.

4. I’m friends with all my exes.

2. I’ll pay.
I’m old-fashioned and like it when a guy pays for the first date. While some people believe it’s important to pretend to want to pay by doing something absurd like reaching for your wallet, this is not a good idea. What if he says, “Sure, you pay”? Will you resent him for it later? Don’t play silly games. If you want him to pay and he is willing to, then let him. Be sure to express your heartfelt thanks afterward.
3. I just have to make a quick phone call. Do you mind?

After meeting someone new for the first time, you’re going to step away to talk to someone else?

Not cool. Keep your phone in your purse. Even resist the urge to pull it out to share those photos of your adorable new puppy; you may see a text or call from someone and be unable to not respond.

4. I’m friends with all my exes.

Your date does not need to know that your exes are still around. Nor does your date need to know to look forward to meeting these exes if you hit it off. Actually, don’t bring up exes at all on a first date—it’s unnecessary.

5. Why are you still single?

Whenever a guy asks me this on a first date, I immediately cringe. I feel like it’s code for What is wrong with you? I never know how to answer, and it just makes me feel awkward. If you’re on a first date with a catch, don’t question why no one else has swept in yet. Instead say something cute like, “You seem like quite the catch! I would love to know more about your background. How did you get into surfing?”

6. I’m thinking about moving.

7. I’m going to chop my hair off.

First dates are attracted to you just the way you appear now, so saying right off the bat that you are going to drastically change your look in the near future could cause them to run for the hills. Also, I’m a firm believer that men and women like long hair, so if you’ve got lovely long locks and are planning on cropping them into a bob, your potential partner might be a little bummed.

8. I’m still totally hung up on my ex. 

If you’re still hung up on your ex, you shouldn’t be on a first date. It’s not fair to the other person, who you’re not really giving a fair chance. If you’re still hung up on your ex and hope that dating someone new will help you forget said ex, mentioning your former flame on the first date is not a good idea.

9. I’ve probably only been on five first dates in my life.
Don’t let on that you are a dating novice! Project confidence, be light, smile, and make eye contact. Your date will never know that you’re inexperienced.

9. I’ve probably only been on five first dates in my life.
Don’t let on that you are a dating novice! Project confidence, be light, smile, and make eye contact. Your date will never know that you’re inexperienced.

Whether you’re deciding what bar to go to next or whether or not you want truffle or regular fries, it’s important to show that you have an opinion. You’re your own person and make decisions all the time, so don’t shy away from doing this on a first date.
11. Actually, make mine a double.

DDTM is an acronym my friends and family use. It stands for “don’t drink too much,” and it’s something you should always remember on a first date. Dates don’t want to be with a hot mess who can’t hold her liquor and needs to be taken home from the party early.

Trust me—I’m speaking from experience. Regrettably, getting too drunk on a first or second date has caused me to lose respect and interest from many an eligible bachelor.

12. How much money do you make?

10. I don’t care. You decide.

Whether you’re deciding what bar to go to next or whether or not you want truffle or regular fries, it’s important to show that you have an opinion. You’re your own person and make decisions all the time, so don’t shy away from doing this on a first date.
11. Actually, make mine a double.

DDTM is an acronym my friends and family use. It stands for “don’t drink too much,” and it’s something you should always remember on a first date. Dates don’t want to be with a hot mess who can’t hold her liquor and needs to be taken home from the party early.

Trust me—I’m speaking from experience. Regrettably, getting too drunk on a first or second date has caused me to lose respect and interest from many an eligible bachelor.

12. How much money do you make?

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