Dating Advice for: "How Do I Not F* This Up?"

dating advice
Jackie, I need some dating advice. Say you go out on two first dates on two consecutive nights and they’re both awesome. How do I not F* this up?


Do you realize how many men and women would KILL to be in your shoes? Over and over again, people dating tell me these nightmare stories about first dates and how it’s almost impossible to meet anyone normal, and how they’d give ANYTHING to find someone they even want to go out with on a second date.


And here’s you. You’re two for two. My gut reaction is to tell you to sit back and enjoy it! You actually met two women you really connected with on a first date! How often does that happen? Never?


How do you not F* it up? Three things:


  1. Relax. You might not have a problem after date #2 with each of them, because without sounding like negative Nancy, you might feel differently about one or both on the second date. In other words, the second date could make your decision for you. But, let’s say you go out with each of them again and you like them both again. What’s wrong with continuing to date both?

I actually have a good friend who was dating two men for almost a year, and was honest and upfront about it to both guys. Her now husband of 15 years and father of their three children ended up telling her that if she didn’t break it off with the other guy, he was done. Does she think she made the right choice? Completely 100%.

I still have a hard time imagining that scenario. What I mean is, I don’t think you will end up dating both girls for almost a year, but my point is that it is possible for a little while, until you figure out you don’t want to take things further with one, or that you like the other one so much that you choose to date only her.


  1. Let things take their natural course. I truly believe as you go on more and more dates with these women, the decision will be made for you. It will become obvious. Furthermore, let’s say you continue dating both and it gets to be date 5 or 6 with each. One or both will sense it and pursue a conversation of exclusivity, especially if things start to get physical. The right decision will become clear (in my opinion.) And by the way, if things do start to get physical with either, I’d suggest not sleeping with both women. That’s just gross. Be a man, not a pig.


  1. Be honest, if need be. The one thing you owe both these women is the complete truth. If one asks, “Are you dating anyone else?” you need to have this conversation. No one enjoys being lied to or lead on. The best way to think of it is, put yourself in the girls’ shoes. Wouldn’t you want honesty instead of investing a ton of time in someone, only to be dumped for the girl he’s been seeing since day one of your relationship?


I’m not trying to make you feel badly about yourself, or feel guilty because you are doing nothing wrong. But I do feel compelled to tell you to do the right thing and be upfront, so if someone is going to get hurt, at least they weren’t deceived in any way. You’re kind of like the Bachelor! Imagine, that guy does it with 25 women, right? You can handle two.

Buy novels by Jackie Pilossoph
Take the quiz to get recommendations Divorced Girl Smiling Trusted Partners


Jackie Pilossoph

Editor-in-chief: Jackie Pilossoph

Divorced Guy Grinning is a blog for men facing divorce and dating after divorce. It's kind of like hanging out with your platonic female divorced friend and hearing her perspective on your divorce and your love life issues.

Leave a Reply

Your email address will not be published. Required fields are marked *