Don’t Ask These Questions In A New Relationship

new relationship

By Jackie Pilossoph, Founder, Divorced Girl Smiling, the place to find trusted, vetted divorce professionals, a podcast, website and mobile app.

Picture this. You’re lying in bed with the man you’ve fallen madly in love with. It’s only been a few months, (still a new relationship) but you are SURE he’s the one. He just kissed you and you feel happier and more loved and content than you’ve ever felt in your life. Finally! You’re done with the dating after divorce scene! Your prince is here! Mr. Right has arrived!

You turn to your guy and look into those beautiful eyes. You can see he’s as happy as you are. And then you ask, “So, when do you think your divorce is going to be finalized?”

If this is a movie scene, this is the moment the romantic music abruptly stops and the audience gasps. What are you thinking asking someone you’ve known for three months that question?? Do you expect him to answer, “Now that I’ve met YOU, I’m going to make sure my divorce is final next week so we can get engaged, move in together, merge our families and live happily ever after!”

I feel I am somewhat of an authority when it comes to knowing the divorced guy. Of course, every guy and his situation are different, but in general terms, I think I can safely say I know a little bit about how the divorced guy thinks.

EVERYTHING MOVES SLOWER. That’s the divorced guy mentality. And that’s actually really smart!

I can also tell you that there are certain questions a new girlfriend can ask too soon–questions that will turn him off so fast, your head will spin. Here are 10 questions you should never ask someone you’ve dated for less than a year:


1.    Where do you think this relationship is going?

He doesn’t care right now. He’s just having fun. That doesn’t mean he will never get serious with you. It just means you both need more time. Let the relationship develop naturally.

2.    When do you think your divorce is going to be finalized?

None of your business! He isn’t going to get divorced and get engaged to you the next day. Does it really matter? Some people have a rule that they won’t date people who aren’t officially divorced. I couldn’t disagree with that rule more. People think if someone isn’t divorced, there’s a chance they might reconcile with their ex. Wrong. Someone can get back together with their ex at any time, even if there’s a divorce decree that’s been sitting on their desk for five years. If someone’s divorce is taking a long time to happen, it’s either financial issues, a struggle to reach an agreement or laziness.

3.    When are we going to introduce our kids to each other?

No offense, but at the beginning of a relationship, the two of you are into each other. Why would you want to jump in and get the kids together? To test it out? I hate that approach. My opinion (and you can take it or leave it) is that you better be pretty darn sure it’s going to work out when you bring your kids into the mix. Because if they get close to his kids, and then you and the guy split up, the kids are the ones who suffer another loss, new friends that they will never see again.

4.    Why don’t you ever tell me you love me?

If you have to say that to someone, you have your answer: Because he doesn’t.

5.    Do you still have feelings for your ex?

Of course he still has feelings for her. She is not only the mother of his children, but the two of them stood in front of God and took vows. He might feel angry or hatred, even, but I think that there’s a part of every divorced person (whether they want to admit it or not) that will always love a little part of his or her ex no matter what.

6.    Did you ever cheat on your ex?

If you ask this question, you better make sure you are able to handle the answer.

 7.    Would you ever cheat on me?

This is sort of a stupid question. Like someone is going to say, “Hmm..I don’t know. Maybe.” The answer will always be “no,” but you will never really know.

8.    Why do you think your kids don’t like me?

Umm…because you’re not mom? It took me a long time to learn not to take anything personal when it comes to your boyfriend or girlfriend’s kids. I bet they DO like you. They just don’t like the fact that Dad has a girlfriend. They want Mom to be his girlfriend.

9.    Are we exclusive?

Again, are you sure you want to hear the answer to this question? “You can’t handle the truth!”-Jack Nicolson, A few Good Men. Don’t ask unless you can handle the truth.

10. Think we will ever get married?

Not if you keep asking that. Let the person get there. Give it time. Especially in dating after divorce, people don’t get engaged three months into a relationship. It’s a longer process and that’s a good thing!

The thing is, I get you. When you finally meet a great guy, even in the first few months, you might know you are in love. That’s wonderful! But what I’ve learned is if you wait a year or two, and you still feel like you did in month number three, then what you have is really real. Unfortunately, when people don’t wait, that’s when divorce number two happens.

Great questions to ask someone you’ve dated for less than a year:

  • What should we do tonight?
  • Why do I like you so much?
  • Why are you so adorable?
  • How did I get so lucky to meet you?
  • Do you know how lucky you are to have met me?
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    Jackie Pilossoph

    Editor-in-chief: Jackie Pilossoph

    Jackie Pilossoph is the Founder of Divorced Girl Smiling, the media company that connects people facing with divorce to trusted, vetted divorce professionals. Pilossoph is a former NBC affiliate television journalist and Chicago Tribune/Pioneer Press features reporter. Her syndicated column, Love Essentially was published in the Chicago Tribune/Pioneer Press and Tribune owned publications for 7 1/2 years. Pilossoph holds a Masters degree in journalism from Boston University. Learn more at:

    3 Responses to “Don’t Ask These Questions In A New Relationship”

    1. Ellen Feldman

      Fabulous advice Jackie. Live in the moment and have fun. Good for you and someone you are dating to feel you can care about another person. Do not focus on the future!


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