How to Explain Your Dating History

Women's Dating

How to Explain Your Dating History

Bethany Heinesh Bethany Heinesh • 9/25/14

One of the most uncomfortable things to talk about with a new boyfriend is an old boyfriend. Unfortunately, the ex-factor is a topic of conversation that has to happen sooner or later. Even though we dread talking about previous relationships and sexual partners, we’re going to have to listen to stories about them at some point and share a few of our own.

Women are far more interested in getting details about her man’s ex than men will ever be. We are fascinated with finding out about his ex-girlfriends. Am I right, ladies? We will ask direct questions to the degree that a date might turn into an interrogation.

  • “What does she look like?”
  • “Why did you break up?”
  • “Do you miss her?”
  • “Do you think I’m prettier than she is?”

When he won’t indulge in our obsession, we’ll do some super sleuthing to fill in the blanks. Cyber stalker, party of one?! We want to know how skinny she was, if she was good in bed, how much he loved her, and where she is now. We have even been known to mercilessly torture ourselves by ceaselessly comparing ourselves to her.

Men, on the other hand, are far less inclined to learn about our romantic interludes. They’re just not wired that way. The thought of you with another man makes your new guy queasy, so he would rather not think of it at all. This means he doesn’t want to hear about that time so-and-so took you to Aspen on a ski trip or when the two of you spent a weekend in bed.

Eventually, you will have to delve into your background because to some degree. Here’s what you need to know when answering his questions:

1. Complete honesty is not always the best policy.

You do not have to tell your man every little sordid detail of your sexual history. I assure you, sharing intimate moments of the physical experiences you’ve had with other men will only create unnecessary problems. Just because he asks how many men you’ve been with doesn’t mean you have to answer. Unless yours is a number you feel comfortable sharing, be cute and say something like, “A good girl never kisses and tells.”


“The great thing about history, sexual or otherwise, is that it no

longer exists. It is in the past, and the past is behind us.”

2. The past is gone, so rock on.

We get to decide how much we want to share with our partner. This means it is OK to withhold information you do not yet feel comfortable sharing. There is no need to recall a time in your life where you executed bad judgment so you can feel bad about yourself, let alone share that with the man you’re dating. As long as it does not have any direct bearing on the present, protecting your past is completely reasonable. Show off the woman you have become, and don’t dwell on who you used to be.

3. Save it for the confessional booth.

If you’re a bad girl gone good, keep quiet about your transgressions. Allow the new man in your life plenty of time to get to know the “real” you before you share any memories with him you’d just as soon forget. When you’re getting to know someone, you are still extremely vulnerable to being rejected. It’s wise to move cautiously when discussing previous relationships and sexual partners. If you’ve slept with a lot of different people, had orgies, taped porno flicks, posed for centerfolds or danced for cash, you might want to seriously reconsider being completely forthcoming with this type of information.

4. If you’ve got a creepy ex, say so.

If you have a psycho ex-boyfriend, share that with your new partner. He needs to know if the two of you are in danger when you go out. Likewise, if you’ve got serious scars caused by some horrifying experience, be open about it. Men need to know why you’re so guarded, anxious and uncomfortable. If you’re freaked out by physical intimacy, say so. If he’s worth keeping, he’ll take the relationship at your pace.

5. Stay safe.

Remain current on your STD status and practice safe sex. Get regular HIV tests and be sure to get checked for all other sexually transmitted diseases. If you come up positive for anything, take care of it right away, and don’t have sex until the doctor gives the green light. Insist that your new partner gets tested and agree to share the results with each other. This will keep you both accountable and aware of the potential risks involved in sexual activity.

The great thing about history, sexual or otherwise, is that it no longer exists. It is in the past, and the past is behind us. If you have ever misbehaved or gone through a promiscuous period you’re not proud of, don’t give it another thought. Everyone is guilty of doing something they wish they wouldn’t have, and you are no exception. Besides, the person you want to be with will accept you for who are and recognize that you’re human.