Cheat Week – Day 3

Would you date someone who cheated? What’s the reason for your answer?

Just A Jenn

Um…how do I know this person is a cheater?  Did I ask?  Oh, wait, I don’t do that.  So I guess the answer is really yes.  Because I wouldn’t know.  When you begin dating someone, you’re feeling them out bit by bit.  You learn more about them the more you spend time with them.  That’s the way it works.  Eventually, their personality begins to emerge, and you decide that you either like what you see, or you don’t.  It’s the dating game.  I don’t play 2500 questions with my dates.  And I certainly don’t discuss with them their past relationships during the initial dates.  I think it’s weird when people do that.  If you’re asking a bunch of questions like, “Have you ever cheated on a partner?”, you sound like a suspicious and untrustworthy person.  If a guy starts asking me questions like that, I take it as a sign it’s time to bow out, so naturally, I’m not going to inflict behavior I hate onto someone else.  The past is the past.  But important pieces of your partner’s past should begin to emerge naturally–in your day-to-day conversations.  And if my partner happened to mention in conversation that he had previously cheated on someone (What are we doing? Watching that show Cheaters?  Anyway…), I would, of course, ask questions to gain more information.  Like I said before, I cheated on a boyfriend once.  But I won’t do it again.  And I wouldn’t want someone to hold that against me.  So I’d want to hear the story.  Obviously, if the guy’s a total player, he’s not going to tell me–I’ll find out eventually.

Now, if the guy is someone I know…and he happens to be a serial cheater–and I know this because I know him, that’s a different story.  And no, I wouldn’t date a known habitual cheater because I don’t want to get my heartbroken.  But if it was someone I knew who had previously had one small indiscretion from which he learned?  Yeah, I’d give him a shot.  Because every situation is different.  And people do change.  Just because he cheated once, doesn’t mean he will again (but I’d be wary).


Can they articulate the reasons behind their behavior? [I just answered a question with a question. I now, officially, suck]

The non-question answer is…perhaps [just as bad]. To evaluate how much a person has changed and if they are safe enough to be dating, I need to ask specific questions about their past and pay close attention to how they answer:

  • #fail “I was unhappy” or “My needs were not being met”. Generally speaking, any deflecting the blame onto the relationship and/or his/her former partner is a clear red flag. This person is still a high-risk cheater because, in their own mind, they were absolutely justified for their behavior. According to their logic, they did nothing wrong. Cheating is NEVER justified under any circumstances [Men come up with some redonkulous logic arguments to justify their cheating1].
  • #fail “…Sorry Bro!”  [Watch it here with Spanish subtitles] Last week’s rerun of How I Met Your Mother featured an ex-girlfriend of Ted’s [Played by the always yummy Laura Prepon] who used cheating as an exit-strategy to a failing relationships. These people are almost always repeat offenders and will likely fuck your best friend before you finally break up. These people cannot be trusted:
    • Strategy #1: Securing a new potential relationship to safely exit and not be alone.
    • Strategy #2: Creating trust issues in current relationship so they can blame their soon to be ex-boyfriend/girlfriend for being a psychotic crazy person [They may be crazy, but exploiting that weakness to your own benefit is diabolically calculated2]
    • Strategy #3: Leaving clues and planning to get caught. Some people want the other person to find out so they do not have to do the dumping.

  • #fail “Things just happened. It was a mistake.” This person clearly has no clue how to keep their pants on. Nakedness doesn’t “just happen.” Next time they are alone with a member of the opposite sex, they will just happen to forget to keep their clothes on…again [Send her to me. I’m offering private therapy sessions…in low-lighting…with candles].
  • #epicfail If, at any time, you think to yourself, “That was her…he will never cheat on me. I’m different. He will never want to cheat!” you are not smart enough to be dating anyone. That’s right. It doesn’t matter whether he’s changed or not. You are too stupid to be dating. Please try again later when you’ve gotten a clue [But please, call me].
  • #win So, what defines a former cheater as a safe bet? They usually start with phrases like, “I was a complete asshole!” and follow it up with a clear, complete, and detailed analysis of the character flaws and identified behaviors that led to the cheating in the first place.
      • If they are aware of what those flaws are, they can then elaborate on steps they have taken to improve themselves over a lengthy period of time. Change does not happen overnight, in a week, in a month, or often even a year.
      • Remember, someone is rewriting how they address the fundamental flaws in their emotional/mental DNA. This takes a great deal of analysis and series of positive choices.
      • To undergo this amount of change requires so much self-reflection, that they will be able to detail it for you. They have to know themselves that well. If they don’t, they haven’t changed.


  1. My wife no longer gives me BJs. I want a BJ. My intern can suck a golf ball through a garden hose. Therefore, I can bet a BJ from her. [In Bill Clinton’s defense, this does qualify as a logic argument…albeit an extremely shitty one].
  2. Both Guido and Cindy used this tactic to try and convince other people that I was paranoid and they were not fucking…Thankfully, no one actually believed them.

Mr. GuyDudeBro

I would never ask someone if they cheated, so I might never know.  My focus is on my relationship with them, not their past relationships.  I might ask why past relationships didn’t succeed and I would expect an objective insightful answer and not just, “he cheated on me,” or God forbid, “I cheated on him.” In short, yes I would date someone who has cheated, but I’d rather not know about it.


Update coming soon…

Thanks to all my contributors!! – TJ

Stay Tuned, Tomorrows Question – If you’re friends with a cheater at what point do you step in and say something regardless of the possibility of dividing up a group of friends? If you don’t say anything are you condoning cheating by being silent?

5 responses to “Cheat Week – Day 3

  1. I know personally I have trust issues seeings how I’ve been cheated on before… I think I’d sabotage my relationship by dreaming up scenarios that weren’t there.

    So if I had prior knowledge of someone cheating, I’d have to strongly exam if I could date them… even if it was a one time thing.

    The fact that it happened once strongly increase the chance that it can happen again.

  2. Pingback: Cheating: A Different Kind of Shark Week « Clue-by-Four: Ramblings of a Jock Dork

  3. thank you this post is very good and nice blog

  4. Pingback: This week… « Life @ Twenty-Something

  5. Hmmmm… these are some loaded questions. As for this one- I’ve been on both sides of the gun so I’d have some understanding if someone brought this to the relationship. It completely depends on the circumstances and the person’s history. I really like what ClueXFour has to say but “I wasn’t having my needs met” isn’t just a cop out. Sometimes cheating is a symptom of an illness that already existed. Not excusing the behavior 100% but I understand the sentiment. All in all this subject matter is definitely making for good discussion points and a wide range of opinions.

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