Sex, Lies & a Very Drunk Co-Worker

Dear Dating Mom:

I’ve been with my boyfriend for close to two years. About eight months ago, I had a one-night stand with my co-worker. We were at an office party and both of us got pretty drunk. Never before nor since then have I ever been with another man, but a friend said I owe it to my boyfriend to tell him. I disagree, because I would never do it again.


One Night Only

Dear One Night Only:

My first question would be, what good does it do? Well, for you, it releases the burden of your guilt, to be sure, but that would be like carrying a 1,000-pound weight and asking him to hang on to it, you know, just for like, forever. Sure, your load would be a lot lighter, but what about his? 


If you know yourself well enough to know you will never do it again, then perhaps you should keep it to yourself. Trust is a big thing between people and remember you can’t “unsay" things just like you can’t "uneat” that bag of chocolate chips cookies, although I would donate a kidney to anyone who could figure out how to do exactly that.

Oh, and for the record, to anyone reading this, please note that if you could also figure out a way to “unsleep” with somebody, that kidney will come with a brand new car and a driver that can only be described as hot and yours for the taking.

Then again, we must ask ourselves, what would be the good of telling him? For many, honesty is the most important thing in a relationship. I don’t disagree, but for me, I confess, it falls below hot, hip, handy, and hooray, he cleaned the house, night everyone!

Now, it might be because six years of being single has made me into a very different kind of person, clearly one that has reorganized her values by what is important to her, beginning with the happiness of her vagina, followed very closely by her inherent laziness, and then her need for 10 hours of sleep, in a row, daily, I might add.

Back to that whole, honesty is the best policy “thingy.” Many have built the foundation of their relationship on this policy, and if that is the case with you, then tell him. However, you must be prepared for him to thank you for your honesty but for f**king another guy? Not so much and then of course, what he does in the aftermath of this revelation.

If it were me, truth be told, I’d be outta there and fast. Sorry. I’ve got the memory of an elephant and the knees to match, and I know that every time my partner was late, ordered the chicken parm instead of the meatball sub, or asked me to pass him the milk, I’d be suspicious and I just couldn’t live that way. But again, that is just me. I know many others who have forgiven their partner and moved on to have a very happy, monogamous relationship.

Actually, I don't, but I've HEARD, so that counts for something no?

Are you a single mom with a question about dating/sex/love? Leave Jessica a question in the comments or you can write to her directly at and she'll answer you in her new column, "Single Woman Walking," at beginning February 1.


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