Infidelity / Long Term Relationships

Sorry Snooper

This classic column originally appeared at the barbershop notebooks where Sex with Timaree runs every Monday.

Question to the Sexpert:

“I have been dating my bf for about a year now and I had just recently gotten comfortable. He’s been divorced, has a hard time opening up etc…. For some reason, I went to his email and guessed his password. He had stuff in there from AdultFriendFinder, but it was only in Nov/Dec. [Note from Timaree: it’s like a MySpace for people seeking no-strings-attached sex.] I went to the profile and there were two pics of his penis, and a handful of messages. I’ve been feeling weird because I can’t mention it to him because I don’t want him to know I went in his email and I feel totally guilty about it. A couple months ago I was on his work laptop and in the history there were things from that site and he was like, “oh other people have had this computer before me.” How do I get over the feelings I’m having? Thinking of him looking at and messaging other girls makes me super sad. Our sex life is great and I feel like I must not be good enough.”

A horrible but true reality about snooping into other people’s private things is: you get what you deserve.

That’s not to say you’re an intrinsically bad person who has earned this awful unhappiness you feel now. It just means violations of trust result in revelations of more violations of trust in an equal and opposite direction. What you do now, to alleviate this awful gunk coating your heart, depends a great deal on your motivations to have looked into his email in the first place and whether or not you want to be in this relationship.

You must first look at what random instinct prompted you to guess his password and scroll back through the last several months. Did you have reasons to suspect he was cheating/lying/stealing/kidnapping the children of heads of state? What did you expect/hope/dread/want to find in there? Validation? Relief? Birthday present ideas?

At the core of your relationship there are big missing chunks. Both of you have shit, cause everybody got shit. He doesn’t want to talk about his shit and you don’t feel right because of that, and because of your own shit. He has a life before you about which he is reticent to talk. It may stay that way forever. Are you ok with that? If not, a year is as good of a time investment as this relationship warrants. Yes, you may love each other, but unless you are both interested in taking all that aforementioned shit and showing it the glaring light of day, it’s just going to be an awful cycle of you chasing and him retreating into his shell.

If, though, you think, “goddamnit, let’s make this work,” there’s hope that you can do just that.

First and foremost: Separate the guilt you feel and the stuff you found. They are independent entities, discrete episodes and unconnected crimes. If you come at him like, “I was snooping and I know it was wrong but what the gee golly goodness is this? Your penis?” then there will be an immediate  dichotomy of “you did this,” “but you did THIS,” “but yours was worse” and no one will get anywhere.

You’ve got to fess up and apologize sincerely, swearing honestly it won’t happen again (and mean it). That alone will take care of a lot of your craptastic feelings right now. Deal with the fallout like the strong woman you are, facing the consequences with your dignity intact. That is integral to the relationship ever moving forward.

Then, after he’s had time to really contemplate this situation (and I mean days, not minutes), then you can think about asking about the email from last year. Bring it up from the place where it now rests: your vulnerability. Explain that when you went in there you saw something you’d like to ask about because it brought up some unpleasant feelings.

Remember earlier when I asked what motivated you to snoop in the first place? Ask him whatever it was you really wanted to know when you went in there. Now you’ll have the moment of truth. What happens from there is scary right now, I know. But if this thing is going to be salvaged, then that moment will have to happen.

Good luck and hopefully you’ll both have learned a lesson.


Do you have a question or comment? Please email Timaree directly at

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