When to Discuss Dating History with a New Love Interest

It’s always so great in the very beginning when you first meet someone. You’re not talking about the past, or thinking about the past. But then, the honeymoon phase begins to end and the two of you get a little closer. At a certain point, it’s going to be time for the two of you to talk about your dating history. Here’s the issue: when are the two of you at that point?

Getting There

As the two of you get to know each other a bit better, things might start to get more serious. You’re spending a lot of time together, you’re not seeing other people — things might progress. Before they can, you might need to mention that time you were almost engaged, or explain that some stuff makes you crazy because of the one who broke your heart. Everyone’s got baggage, and you have a good idea of the stuff you’re carrying around with you. If you want to take that next step, if you’re thinking about moving in or building a future together, you’re going to have to open up those bags.

How to Talk About It

Even if it’s the right time, it’s the wrong subject. It will never, ever be pleasant to talk about the ghosts of dating’s past with a current love interest. Unfortunately, it’s not a topic you can avoid forever. They need to know about your triggers and your hang-ups, and all the things that could come between the two of you.

But it’s difficult to make that conversation happen. First, make sure it’s a good time to talk. The two of you should be in a quiet place and relaxed. Don’t bring it up if someone is engaged with something else, or already angry about work. Wait for a quiet moment, and then break the conversation ice by talking about how much you’re enjoying the relationship. Tell them you don’t want the issues that have wrecked relationships in the past to be a problem in the present, and then talk about that.

The Bombshells

Now is the time to talk about your divorce, your kids and anything else that you would want to know about from someone that you’re dating. If there’s information you’ve been withholding, it’s time to come clean. This conversation can and has ruined potential romantic pairings, but that’s why you’ve got to have it. If there’s a skeleton in someone’s closet that is a total deal breaker, it’s better to find out early on in a relationship than finding out after you’re already sharing a drawer.

The Right Time

There’s never a perfect time to have a difficult conversation, but there are bad times to bring up your past with a current partner. Wait for conditions to be right, and wait until you feel that you’re truly ready to take your relationship to a stronger, deeper level of intimacy. It’s a good idea to wait until you’re pretty sure they’re ready for that as well. Having the conversation is rough, but it can lead to a much stronger and better relationship.

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