We all have baggage.  For some people it’s a small little carry-on.  For others, it’s a 200lb steamer trunk.

Maybe you got a quickie marriage and annulment in Vegas.  Perhaps you have a felony. It could be that you can’t have children.

As we all have a past and possible issues, struggling with when to bring it up in a relationship is always a stressful decision.  If it’s done too soon, the person may ghost. If it is brought up too late, the other person may feel deceived. Even if you know the right time to bring it up, you may struggle with how to bring it up.

Since it’s something we all have to wrestle with at some point, here are some tips to (hopefully) make it easier.

Relationship Baggage 1c

Don’t Overshare Too Soon

While you may be excited to being finally going out on a date again after your last horrible breakup, it is definitely not the time to use your date as a stand-in therapist.

The first date is supposed to be light and airy. You can talk about all of the other stuff in future dates.

“A guy I was on a first date with mentioned he went down on his best guy friend but it was beautiful and he didn’t regret it but he wasn’t gay of course.” – Amber G.

The sentiment is fine. Saying it on a first date is not.

The More Serious it is, the Sooner it Should Be Brought Up

If you once had a miscarriage with a former boyfriend, that is something that you can hold off talking about until you are deeper into your relationship.

But, if it’s something that is immediately obvious or that will impact the relationship strongly, it’s better to talk about it sooner. Telling him you have a child can wait until date 2 or 3.  But sometimes, if you can’t hide it, it’s better to confront it sooner.

“I had a girl tell me she had MS [multiple sclerosis]… but I appreciated her letting me know. It didn’t feel like an overshare the way she shared it. She said she had health issues, that she was open about them and wanted me to know that she was taking care of it.  She was confident when sharing the info.” – Sarah J.

Relationship Baggage 2c

Be Conscious of How Much Weight You Put On it

The “how” to tell can sometimes be the most difficult.  Just understand that the amount of weight you put on it is telling them how much of an issue it is for you.

I had a client that would, very seriously, sit a girl down that he just started dating and tell her that he had Crohn’s disease.  Now, Crohn’s disease is not nothing, but he was putting so much weight on it, that it would freak out the women.

If you are able to mention it, almost in passing, it helps to lessen the impact.  If she mentions going to a ball game say, “Sounds fun! I just have to make sure we get seats near the restroom so my Crohn’s disease won’t spoil the fun!”


Hunt Ethridge is a Hoboken-based dating consultant and a fashion writer. Currently, he is the Senior Dating Coach at New York Dating Coach (www.newyorkdatingcoach.com).