Will He Cheat On Me If He’s Done It Before? [Ask A Dude]

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Dear Dude,

There’s a guy (always is, right?), and he’s really cool and all, and we get along really great together. We’ve hung out a bunch of times, but here’s the thing: he’s got a reputation for cheating. I mean, I know from friends that he’s cheated on at least 2 girls before. And I asked him about it, and he got really upset. He said he wasn’t upset with me, but that he’s been mad at himself for doing it, and that he should never have been with those girls in the first place. But he also didn’t think he did the right thing regardless. He sounded sincere, and I kind of would like to see where this goes. Can I trust him? Will a guy that’s cheated before definitely cheat again, or does it depend on the relationship? I don’t want to give him my heart to have him smash it. What do I do, Dude?

Fighting With Herself

Dear Fighting With Herself,

You run, run, RUN! No, jk, you don’t have to run, yet. You’re treading on some tense territory, and you know it. That’s the good thing. It’s a good sign you’re on your guard about his past rather than oblivious to it. That means you’re taking care of yourself. You’re on a good path here and you seem to be at least somewhat emotionally equipped to deal with the situation. Problem is your situation’s a freaking mine field. Because when one’s got a reputation-a deserved one-for cheating, it’s tough not to expect the worst even if you’re hoping for the best. Even if you’re working for the best.

Cheating can be a specter looming over every interaction in your relationship. Every girl he glances at, every flirtation in a group, at a party-or perceived possible flirtation-it all becomes a small trigger of warning. And that kind of alertness in your future is either something you learn how to work through or it’s cancerous. There are a few questions to ask yourself:

Can I handle being cheated on?
Could you? You know the risk and thus you’ve got to do your best to prepare yourself for the result.

Do I think what we might have is worth the risk?
This is a question for your gut. Is the sex amazing? Are you two finishing each other’s sentences? Do you find yourself hoping against hope? Or are a bit more, “meh” about the chemistry?

How can I come up with some boundaries to ensure he’s behaving?
Practicality at work. What can you two do, together, to kind of acknowledge the fears you have but at the same time ease them? Trust building as it were. Is it a calling schedule? A promise about checking in? Is there a test where you can stick his dick in a tube of medical fluid and see which color it turns, like a pregnancy test?

And I’m going to help you out. Here are the answers to all of these questions and all of the others you have about what could happen: You won’t know until you try.

Oh, you can make all the rules you want, create as many boundaries to give yourself a sense of security, but you’re playing with getting hurt by someone else’s choices. Not yours. That means you will never get a 100% guarantee that he’ll always remain faithful to you. But then again, even if he didn’t have this history, you wouldn’t have that…so how long have we been in the TARDIS then?

People can change. They can adjust. It’s totally possible you can learn to trust him not to cheat on you. Right now though, it doesn’t sound like you have that trust yet. Unfortunately, you’re going to come to the point where you decide to trust him or you deal with the consequences that you can’t. Are you at that point? I don’t know. That has to be your call.

No one’s promising marriage. You’re not moving in together. Just take it one day at a time. Again, if you think he’s worth it. If you think what you’re feeling is something that you’ll regret NOT exploring. That part’s purely subjective though, and you’re the only subject that counts.

The voice of the voice of the voiceless,

The Dude

[Got a Dude itch you just can’t scratch? Sick of trying to come up with a not-totally-crazy-girl way to bring it up to your guy friends and get their take on things? Totally over over-analyzing the cryptic messages he leave on your Facebook Wall? We got your back, girlfriend. Send your question over to askthedude [at] collegecandy [dot] com. The Dude won’t sugarcoat it, beat around the bush, or any other weird cliche that means lie to you. Like a nice, juicy hot dog, he’ll be 100% real beef, 100% of the time. So bring. it. on.]

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