25 Things A Guy Should Never Say On A First Date

This one goes out to the fellas, the home boys, the dudes that just don’t understand why they can’t get a second date. Here is the thing about dating – it is awkward. It is expected that you are going to have moments where you say something dumb that you wish you could take back. It is expected that you are going to have moments where you embarrass yourself and hope that your date can forget that bus crash moment. And then, there are moments where you have just blacked out and do not know what you are even saying or doing wrong. The moments where you should have just stopped right there, asked for the check and let the pretty little lady go on her merry way before you gave her a reason to stop at the liquor store on the way home or to reason to write something like this.

Gentleman, here are some handy, dandy tips for things you should never say to a woman on a first date (or really ever):

1. I am not really good at dating. What are we doing here exactly? Am I getting Punk’d? Again?

2. I lost my job recently and have no motivation in life to get a new one. To each their own good sir, but I ain’t about to be your sugar mama.

3. I still live at home with my parents. I need someone to take care of me. You are a big boy, you can pick up your own toys.

4. It is so nice to get out once in a while; I can’t tell you the last time I left the house! Remind myself to pull out my mace when walking to the car so my life doesn’t turn into that movie, The Room.

5. You look so much better than your pictures. I was a little worried there. Well you are shorter than me and your said you were 6’1″, but you don’t hear me complaining, LeBron.

6. I have a roommate. She is a female. I have only slept with her twice, but we were drunk so it’s okay. Ummmm…

Target-Lady-Low-Riders7. You seem nice. My ex-wife was a complete crazy bitch and stole our two cats. They were like my kids. Couldn’t we have save that for after the appetizer?

8. This is so nice. The date I was on an hour ago wasn’t as much fun. Romantic.

9. Do you want to go Lady and The Tramp on this spaghetti? Classy.

10. So how many guys have you slept with? How many girls? Check please.

11. I don’t know if I could commit to someone for forever. Oh how refreshing and out of the ordinary.

12. Why are you single? I mean there has to be something wrong with you. In this moment, there is just SO much wrong.

13. I don’t believe in love. Sir, you just keep getting better.

14. I am not looking for anything serious.  I am just a guy looking for the fun. In other words, you would just like to sleep with me.

15. My girlfriend and I are in the process of breaking up, so this is good this is working out. Can I go get a drink with her instead?

16. How many guys are you actually talking to? I know how you Tinder girls can be. Not enough to get me out of this train wreck.

17. Do you want to go halves on this dinner? I am on a budget. I would have been okay with a box of wine and Sheetz. Alone.

18. I voted for Hillary Clinton because I am all about women in power. Great.

19. I voted for Donald Trump because he is funny. Oh brother.


20. So what does your mother look like? I am trying to picture what you look like when you get older. I am trying to picture myself anywhere but here.

21. Can I kiss you goodnight… At my house… In bed? I am afraid your parents will still be up cleaning up your toys and making you a late night snack.

22. Next time I really want you to meet my parents. I think they would really like you… I am being pulled into a cult I know it.

23. I can picture how our children would turn out. Hopefully they would have my nose though. So glad I can’t see into the future like you.

24. How long do think it will be before I can see you again…or sleep with you? Counting down the years over here.

25. So how did this rate on the date scale? Did I do well? You ruined me for other men sir.


First dates are difficult to begin with, do not make it more awkward than it has to be. Remember that you are not alone here, she may be just as nervous as you are. Keep it light and easy; basic questions about her family, hobbies, and interests will keep the conversation going and give you a chance to see if she is a fit for you.

Just keep in mind fellas, we are all rooting for you… Keep your head in the game and think before you speak!

Featured image via screen grab of That Awkward Moment.


  1. I’ll bet you really impress the guy with your organizational skills when you pull out the checklist of all the things he’s about to say/do wrong.


Please enter your comment!
Please enter your name here

This site uses Akismet to reduce spam. Learn how your comment data is processed.