Dear Em & Lo: I Cheated on My Boyfriend And Don’t Regret It

Dear Em & Lo,

So I am currently in a relationship with my boyfriend of 8 years, going on 9. We have been together since high school and are now in our mid twenties. I love him very much and used to see myself spending the rest of my life with him up until just a few weeks ago.

My girlfriends and I decided to take a little weekend getaway and on our first night there I met the most amazing guy. Instant attraction. We ended up spending the night together which turned into morning. He also ended up switching his flight so we could spend another day together. We met up for the last time and I could honestly say it will be one of the most memorable weekends of my life.

Now I’m scared to face what this means for my relationship. Am I not as happy as I thought I was? Am I settling because I’m comfortable with my situation? I know nothing could ever become of my weekend fling, but now I can’t help to wonder what else is out there for me.

I feel selfish for letting any of this happen, but the scary part is, I don’t regret it because of the amazing connection I encountered. My boyfriend is far from affectionate and does take me for granted at times, so I cant help but feel frustrated with where I am in life. Do I let him go? Do I stay and make things work? HELP!

— Dirty Weekender

Dear D.W.,

We could be like one of those annoying therapists who leans back in their chair and says, “Well, what do you think you should do?” Or, “But what do you really want to do?” But today, we’re feeling kinda prescriptive. Today, we’re going to tell you exactly what we think you should do.

Dump. Your. Boyfriend.

You cheated on him, and not just a drunken one-time thing, but repeatedly, over an entire weekend. Sober, in daylight. In fact, you two actually extended the weekend to make the cheating last longer. Worse, you don’t feel bad at all. In fact, you seem to think that the fact that the cheating experience felt so awesome — um, yeah, it does, but so does sex on meth — is what makes it more than okay. And then you attempt to justify the cheating by saying that your boyfriend takes you for granted.

Er, he takes you for granted?

We get it. You got together young, you never got to sow your wild oats, you’re an entirely different person than when you first met — hell, Miley Cyrus was still Hannah Montana when you first got together. It makes total sense that you’d want to see other people and fuck other people. We don’t fault you for that part at all. Whether or not you two are meant to spend the rest of your life together, this is an indisputable fact: It’s time to take a break, either mini or major.

So, start by breaking up with your boyfriend. If you think you’d like a future with this guy, then you need to be completely honest with him and tell him all about the weekend — because you can’t lie now and expect to get back together with him later. But if you want a clean break and you think this is it for good, then it’s fine to just break up with him and leave out the bit about your sordid weekend. (We hope it goes without saying that if you decide to disregard our advice and stay together with your boyfriend, then you absolutely need to tell him about your major indiscretion.)

You could tell your boyfriend that you just want to take a “mini break,” a la Ross and Jen, but if you go this route, then you have to tell him about the cheating — because in that case, you’re still sorta, kinda together. Personally, we’ve never put much stock in this approach, but we know it works for some people. Feel free to give it a try, but be prepared for a lot of misunderstanding. (We were on a break! It was a mini-break! And so on.)

Oh, and to answer your questions: Yes, we guess you weren’t as happy as you thought you were. Yes, you may well have been settling. Yes, nothing will ever come of this fling. As to what else is out there for you? Casual sex, hot sex, heartache, heartbreak, booty calls, unrequited love, more hot sex, more heartbreak, bad first dates, bad sex, bad dudes, nice dudes you’re not attracted to, hot dudes who don’t return your phone calls — and maybe, just maybe, the man of your dreams.

Now… Tell us what you think you should do.

Couch Potatoes,

Em & Lo


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14 Comments on "Dear Em & Lo: I Cheated on My Boyfriend And Don’t Regret It"

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i thought he was the one. I was fully prepared to marry him. he cheated and it hurts that he never told me, i had to see messages on his phone that were naughty, he made a lame excuse that made sense in the context of the messages and that they never actually met up like the conversation suggested and i believed him because im an idiot. I was always honest with him, always did things for him, and now i cant trust anymore. its hard, it hurts, but what can you do. someday i will find the one, but… Read more »
To Lisa
Lisa, i am deeply concerned. You need to tell your boyfriend. He is fully committed and ready to walk you down the isle. It will be tough but if you ever loved him enough to say yes when he got on one knee, you need to respect him as a human being and tell him your not ready AND what happened. If you do love your fiance like you say you do, you still need to tell him. If he loves you it will work out, but the betrayal might be too much. He deserves to know because he deserves… Read more »
Exactly same situation.. being with my fiancee 2 years now, cheated on him 8 months ago and then the other night went to the club the man who i cheated with works and now speaking to him again. I know its not fair on either of them but its really no fun for me either.. its one of the hardest decisions ever. I love my fiancee but i really like this guy. But what if i finish my boyfriend and this guy doesnt want to be with me and i end up alone.. which i probably deserve. I really love… Read more »
^guinevere This is a big problem with people today. “It’s all about me me me and nobody else” mindset. To clarify, I’m totally on board that young people should be having fun, and that your needs are important as a human being. After all, how can you make someone else happy if you aren’t? But when you can’t draw the line and realize that you aren’t the only person that has wants and needs in this world, especially when in something that involves two people (relationships), and that you can’t have everything you feel you deserve, and you can’t feel… Read more »

At the end of the day it’s your life, and it goes on. Why deprive your self of life when its so short. There’s opportunity in every direction either with a new interest, or some other sorts. It doesn’t matter as long at the end of the day your happy.

See girl, you are doing a mistake, by not letting your boy know, if you love him so much, you could had broken up with him, if he didnt take you granted, what made you lie if you can’t respect a relationship. If he is never yours, and you are never his, then you should not keep him, you should tell him and let him go, now his friends are laughing at him, at your friends too, at least he can keep his distance from the guy and your friends so he would not be embarassed from them knowing who… Read more »