Should I start an affair?

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Dating as a single mother in my 20s by Sabrina

Some recent questions for THE GUYS:

My boyfriend is on dating sites; is he cheating?

Why does he have a secret Facebook page?

From a guy’s perspective; is my marriage over?

He won’t bring me out with his friends

Friends with benefits: why me? 

Kissing Cousins: Should we date? 

Casual Encounter on Craigslist: Is my relationship over? 

Dumped by text

Does future career always trump future relationship?


I am in a long term relationship but have a very serious attraction to a guy in my office. He is also in a long term relationship.  I think he has some interest in me as well, but he is the smart/shy type, so it is difficult to tell how far he is willing to take it.  I don’t want to end my relationship or his, but a short lived fling sounds kind of fun.

How do I get him to move on this or is it just a bad idea all together?


Dear Lauren,

Thanks for your question.

If you’re asking for our “permission” to cheat then the answer is a definitive NO. And maybe that’s exactly what you were hoping we’d say, otherwise there’d be no reason to consult our opinion.

Your interest in this other guy more likely stems from something missing in your current relationship, rather than how amazing he is. So before you move ahead with something you’ll regret, why don’t you take a hard look at what’s going on between you and your boyfriend? Is there a lack of communication between the two of you? A lack of affection? Are you not on the same page with some important issues? Are you putting in more time than he is? Is the distance too much? Maybe you’ve fallen out of love with him? What is it? It’s critical you get to the bottom of what is really going on for you.

On the flip side, we understand that a short fling SOUNDS fun. But it’s fantasy. And honestly, that’s where it needs to stay. Keep your attraction in your mind. (There’s a lot you can do with it right there.) Once you move the fantasy to the real world only trouble will ensue. That’s when people’s lives are altered forever.

If you find that you can’t stop yourself from pursuing this other man, at least deal with your current situation first, and then proceed forward. You’ll be glad you did; and your boyfriend will appreciate your honesty, even though he’ll be sad, and possibly angry about the breakup. (It’s much better than you cheating on him.)

And finally we’re wondering what kind of guy this co-worker is who might consider cheating on his partner? (Of course you don’t know if that’s true or not, so we’re speculating.) Maybe in the fantasy world that doesn’t matter, but it very much does in this one.

Good luck,


ps. Let your friends know about us. Thanks!

4 Comments on Should I start an affair?

  1. Are you kidding me?! First don’t let those guys brainwash you! Sometimes you have to follow the “rules of the nature” instead of those of society. I know what you mean, you have probably found the man that you want to spend your life with, but there is this physical attraction…which its really ok! We all are animals! Dont forget! And you sound like an alpha girl (hot!), so dont feel ashame about it. I have no answer “how to start an affair”…But if you want something go get it and the best way its to catch opportunities! Hope for you that the guys gonna wake up!

  2. @John……Really?….What we’re saying is, if she wants to follow the “rules of nature” as you say, she shouldn’t drag her boyfriend through the mud. Why not just be single? Then she can be free to pursue whomever she pleases.

  3. Hey guys,

    I’ve been married for 11 years and unhappy for most of it. We have two children together. I’ve been thinking about getting out for awhile now. A guy friend whom I went to school with and was best friends that I was madly in love with recently moved back to town. We always had a way with each other that it seemed like we were the only people in the room together. We’ve always had a flirtatious thing between us. We’ve talked over the years and kept in touch. I hadn’t heard from him for the last 4 years though and all of a sudden moves back to town and contacts me. He knows I’m not happy in my marriage. We met for lunch to catch up then he kept texting me. We have been talking and he asked me about having sex with him. I told him I didn’t want “friends with benefits” and I was married, unhappy yes but still married.  He apologized for complicating things. But then we met to talk and ended up making out for two hours, then I told him no to sex. We talked a few times after that about wanting to need some time to figure things out. One week later, we met again and was talking and then one thing led to another and we had sex. He told me its what we’ve both always wanted and couldn’t believe we are here. What do I do now. He’s the one I’ve always been in love with and wanted. I just don’t want to be played. I need to know what he’s thinking so I can figure out what to do in my marriage. I’ve never cheated before or had anyone else. My husband and I were both virgins when we got married. I’m so confused. Could you please help me understand what’s going on????

    Thank you,

  4. @Tammy……We strongly advise you to figure out what’s going on in your marriage BEFORE you go any further with this man. What’s happening with this guy is a symptom of what’s going on—or what’s not going on—in your marriage. Meaning, you shouldn’t leave your marriage for this guy, specifically. First, you should figure out if there’s a way to fix what’s broken in your marriage, or if not, you should make the decision to leave your marriage and start a new life. (And you have lots to consider with your children, etc.) All of these actions should be independent of what’s going on with this guy. All this affair is telling you is that something is wrong in your marriage, otherwise you wouldn’t be open to any sort of affair no matter how attracted you were to the guy. Does this make sense? We advise you to stop the contact with this other guy for now—it’s only going to confuse you—and focus on what to do about your marriage. Fix it if it can be fixed, or move on if it can’t.(Might want to see a couples counselor.) If you end up deciding to move on, then it’s okay to try to rekindle something with this other man. Per your other question: We have no idea if he’s playing you or not, but we do know he’s got much less to lose than you do either way. So think hard about this before you continue. Does this help clarify anything? Please feel free to ask as many follow up questions as you’d like.

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