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Online Dating Magazine > Columns > Date & Relate > Skeletons in the Closet

Date & Relate
by Sara Hodon

Letting Skeletons Out of the Closet

Everyone has those little secrets about ourselves that we hope will stay secret.  It could be something mild, like sneaking into the house after a wild high school party.  Or it could be something not so mild, like a prison record.  The question is—when is the appropriate time to let those skeletons out of the closet when it comes to a new relationship?

I talk about this a lot with a friend of mine.  Like most matters of the heart, it’s tricky business. It depends on what the deep dark secret is, and it depends on how serious you think this relationship might become.  For example, there’s a big difference between someone who has a history of depression and someone who is a recovering addict.  Even if the person’s been clean for years, would you still look at them a bit differently?


It’s hard to know when to share some things with a date.  On one hand, you want to be as up front and honest as possible so you can’t be accused of holding back important info.  But on the other hand, if you share, well, less than endearing things about yourself too early in the relationship, you run the risk of having your date look at you in a different (and maybe not so flattering) light.

Personally, I don’t like liars, so I’d rather know the things that could affect me as early as possible.  I’d rather make up my own mind than be in so deep that a breakup could be devastating for both of us. 

I wrestle with this topic quite a bit, actually.  I was in a long-term relationship with a guy who kept some pretty major things from me—things that definitely had an impact on me, not to mention our relationship. I got some of the details a little at a time, usually after something bad had happened (such as the cable being shut off because he hadn’t paid the bill in months).   How would I have known that he’d been horribly irresponsible with the credit card in the past, and was buried under a mountain of debt?   The secrets snowballed, and it eventually came between us.  It wasn’t until we were practically ready to break up anyway that more of the truth came out, but by then it was too late.   My feelings of trust had been totally destroyed, and to me if there’s no trust, there’s not much left to the relationship.  But I wish I would’ve known earlier.  Would I have pursued the relationship anyway, knowing it wasn’t going to go anywhere?  I feel that I sort of wasted nearly 2 years of my life (but have gotten endless material for columns out of it, so it wasn’t a total loss.)

A more recent guy was up front about the fact that he was divorced, so I knew that pretty early on.  The night before we were supposed to meet, he clarified that he was in the middle of the divorce.  Well, that’s a little different.  I cancelled the date because I didn’t want to get hurt—I’d just been through an experience with someone in a similar situation.  Things seemed great at first, but then the guy decided he wasn’t ready, and I wasn’t about to go through that again.  So I backed out.  This other guy took the risk of being honest, knowing that I might do exactly what I did.   I still stand by my decision (we eventually tried it again a few weeks later and it was great), but I was glad to know what I was possibly getting myself into, rather than finding out much later, when it may have been too late. 

What if you have the deep dark secret?  I’m pretty open with the guys I date—sure, I’ve had some relationships and done some things I’m not too proud of, but I’m lucky in that I’m not harboring any secret husbands, felonies, addictions, or things that might make a potential date think twice. 

Everyone has baggage of some kind, and I think that if a person is committed to getting themselves straightened out and righting any past wrongs, they deserve a second chance to do that.   But the reality is that a person’s baggage could very well cost them a great relationship, and they need to accept that.  I think that most people appreciate the honest approach, though.   I recommend coming clean fairly early on, but maybe not during the first phone call or the first date.  See if there are any sparks first—if not, then you just bared your soul for nothing.  If you truly care about the other person and want to get a serious relationship off on the right foot, I wouldn’t go any longer than a second date to be completely honest with them. 

And then be ready for a wide range of reactions.

Changing your life for the better and owning up to past mistakes isn’t easy, but it can be even more difficult if you’re also looking for true love.  Sometimes just admitting to past mistakes that could possibly affect your future is an important step in setting things right.



Date & Relate is published every Thursday by Online Dating Magazine columnist Sara Hodon. She can be reached at

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