ALW’s Five Guys Q.3: Feeling Undateable and Unfaithfulness

ALW’s Five Guys answer readers’ questions about the sometimes frustrating, sometimes confusing, always engrossing subject of modern relationships. Your questions will be kept anonymous, unless you wish them not to be. Ask your question here!

Hey 5G, I’m feeling a little bit down. The guy I’ve been casually hooking up with for the past year just told me he could never date me because of my history of having been unfaithful to both of my previous partners. Am I undateable? This question has been running through my mind on a loop since I received this text from him: “I like you, but I’m not going to date someone who has cheated on both of her past boyfriends.” That’s a fair assertion, is it not?

I’m a cheater, and it’s safe to say cheaters are pretty frowned upon. I completely do and admit to my fault, but I don’t really feel like a cheater. I was in both relationships for multiple years; the first for two (we were never actually “dating” but we were serious with each other and seeing each other on a consistent basis), the second nearly three. During the entirety of those two and three years, I was faithful to my partner up until the very end (so I guess I’m not completely incapable of committing to someone for an extended time). Both of my relationships definitively concluded when I made the conscious decision to be unfaithful and then used that event as a means for escape from the person I was dating instead of just breaking up with them.

Even though I was the one doing the cheating, I was the one who broke up with the partner I cheated on. I guess I sort of felt like the people I was with were too much of “nice guys” to break up with even if I was unhappy (I mean, my first boyfriend forgave me for cheating and still wanted to be with me). They loved me endlessly, and maybe that makes what I did more horrible but it also made it more difficult for me to express how I was really feeling and the fact that I didn’t want to be with them any longer.

The cheating in both relationships wasn’t spur of the moment, it was a long time coming. I was unhappy in my relationships for a number of reasons (my last and most serious boyfriend was super emotionally abusive and would never let me go out with my friends unless he was there, controlled all of my plans, pressured me into sex to boost his ego), but my partners weren’t on the same page. The longer I dated them, the more they loved me. The longer I dated them, the less I loved them.

See, many people tend to think that “once a cheater always a cheater,” but I sort of see it as relative to the person I’m with. I don’t think the people I was with were the people I was meant to be with long term, and I think that I was afraid to admit and unsure how to communicate that with them. I genuinely did not want to hurt their feelings, but in trying to do so I ended up hurting them even more than I would have had I just been honest.

But does this mean I’ll never be able to have a healthy relationship? That I’ll continue to use cheating as an excuse to leave? I was wondering if you guys had any thoughts.

Hey there! I think this is a very important question to be asked. As a reformed cheater myself, I certainly feel your existential pain. You have caused heartbreak and feel the residual aftershock of the chasm you’ve caused in someone else’s life. In short, it doesn’t feel good to make other people feel bad. You view your cheating as a way of balancing an unfair or undesirable partnership. I see it as chickening out of having a hard and uncomfortable conversation. I don’t think you stayed with those guys because they were “nice guys” – I think you are the one who is too nice, and that the larger question is can you learn to be assertive and develop the self worth it takes to control who and what is in your life?

But, let’s pretend this is a year and a half ago when I believed having multiple guys in your life was a genuine, tried-and-tested, holistic approach to dating. If I were writing this in 2016, I’d argue that because men are innately inferior social creatures, maintaining a healthy, happy relationship requires an emotional overexertion on the part of the woman. And because this outpouring of energy is seldom returned or replenished, we are owed the mental relief of having multiple guys in our lives. Because one will surely drive you crazy, you add a second (or third) to take your mind off things.

It’s sort of sad to admit that this approach worked for me for a while, and I’d recommend it to friends when they were at their wits’ end as to why things weren’t working out with a guy they liked. But there’s some fine print to this approach – it only works when you’re in a relationship you really, really shouldn’t be in in the first place.

The first situation you mentioned can’t even be classified as a relationship because you were never actually “dating,” just seeing each other “on a consistent basis.” So, this guy either didn’t want to commit to you in a serious way in the first place, or you had reservations off the bat about hubby-ing him up.

This second boyfriend is problematic. Emotionally abusive? Pressured you into sex?! You mention this so casually (within a set of parentheses) as though you’re describing an argument you two had on where to get takeout. For three years, you were with a guy who wouldn’t even let you see your friends unless he was with you. That is not normal, not okay, and not someone you deserve to deal with.

And this is when we get to the really important part: If you don’t – quickly – learn how to say “NO”, how to say “I DON’T WANT THIS”, how to say “THIS IS NOT GOOD FOR ME”, you may find yourself in a physically dangerous situation with someone who won’t be such a “nice guy” the next time you try to leave.

You say you cheated as a “means of escape” – that is powerful language to describe a breakup, something that is otherwise a commonplace occurrence. Cheating was perhaps the only tool you felt you had in your arsenal to end unhealthy relationships. You’ve got to develop a wider set of tools.

There is strength and power in knowing what you want, what is good for you, and then politely demanding it from the world around you. Being assertive means being the gatekeeper of who and what enters your life, and then having the self worth to close the doors on people who suck your energy or threaten your glow. It is harder to say “no” than to say “yes.” It takes practice. Listen to this episode of Dear Sugars featuring Oprah (God’s gift to the podcast world) titled The Power of No. It’s a good place to start.

You will absolutely be able to have healthy relationships, but you’ve got to develop a healthy sense of self first. My cheating days ended when I no longer had a reason to cheat; when I dated someone I respected and who respected me. You may have to go through a few boyfriends to get there, but if and when you know it’s time to walk away, just be a big girl and break-up with them *gasp* using words and eye contact.

And you can start with the douchebag who said he couldn’t date you because of your past. – L

L is an almost 24-year-old (#scorpioseason) California girl. “If I was on a deserted island, I would bring kale, quinoa and a camera.” 

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