The 14 Days After Q&A: Why Do Men Really Cheat?

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Why do men really cheat?

Dedan Tolbert: While this question is often an extremely complicated one, the first step is to identify what “stage” your man is in at that particular point in his life. When I say stage, I mean that all men go through 3 stages for what they are looking for from women. These 3 stages differ from man to man and are often based on the man’s maturity level.

One stage is the “dog stage”. This stage is where men just want to have sex with as many women as possible as fast as possible. They don’t really care about the woman’s feelings at all. Another stage is the “player stage”. This stage is when a man finds someone who he’s interested in settling down with but he still wants to have his fun on the side while dealing with multiple other women. The last stage is the “wifey stage”. This is when a man is truly interested in finding a wife or a girlfriend and really being committed to her. I’m not saying that men won’t cheat during this stage, but it’s not what he’s setting out to do mentally.

So overall, there’s no easy answer to this question.When it comes to the question of why a man is cheating on his woman, it depends on what stage he’s in when he cheats.

Cassandra Washington: That’s a great question. From what I hear from a lot of men, some do it just because they can. You know, to see if they still have it like that. Some do it because they feel constricted or neglected in their current relationship. What men are missing in their current situation, they’ll try to find it outside. It’s never a good idea, but hey, it happens because they are human. Humans make mistakes. I will say, however, with the way the world is today with disease, pregnancy rates, violence, etc, cheating is never a good idea. You can’t fix what’s inside, by going out, feel what I’m saying?

Big Boom: It’s fun and it’s easy to do. It makes some men feel like they own the world. If you don’t know any better, you feel like it’s part of manhood. Some guys learn from the best, which would be there father.

Tanya White: In my opinion, men cheat because they have not been honest with themselves or their companion about what they truly want and need not just physically but also emotionally and spiritually. Instead of patiently waiting to find the love they really want and deserve, they settle for what I call “Might As Well Hell” by staying in an unfulfilling relationship and pursuing another unfulfilling relationship on the side. (For complete explanation of what I mean by “Might As Well Hell”, read issue #158 of Tanya’s Tips newsletter via

The 14 Days After Q&A is a relationship mini-series. For the month of February, each day after Valentine’s Day will feature a new relationship question to be answered by two female and two male authors who have written books about relationships. Click here for more information about the authors Tanya White, Cassandra Washington, Dedan Tolbert and Big Boom.

Sun 02-15-09 Do you have to be a freak to enjoy great sex?

Mon 02-16-09 Is sex overrated?

Tue 02-17-09 When should men draw the line in role playing?

Wed 02-18-09 Why do men really cheat?

Thu 02-19-09 Why do I date the same people over and over?

Fri 02-20-09 Why are men challenged by their perineal G-spot?

Sat 02-21-09 Do I tell my friend she’s dating a married man?

Sun 02-22-09 How do I tell my husband I’m sexually frustrated without hurting his feelings?

Mon 02-23-09 Would more racial boundaries break if more people dated interacially?

Tue 02-24-09 How do I cope with not trusting my girfriend after catching her with another woman?

Wed 02-25-09 How do I get my boyfriend of 8 yrs to understand my desire to marry him with losing him?

Thu 02-26-09 How do I cope with my boyfriend sending me mixed messages?

Fri 02-27-09 I fell in love with my best friend’s wife. What should I do?

Sat 02-28-09 Each author gets a special question just for him or her.

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24 thoughts on “The 14 Days After Q&A: Why Do Men Really Cheat?”

  1. Love it! For the sake of a little debate, I find it very peculiar how when it comes to men and cheating, it’s dismissed as a pastime, or something that isn’t necessarily right, but it happens kind of situation. However, when the tables are turned, and you have women who do the same thing, stepping out of her relationship because she can, or because she’s not ready to settle down, or she’s in an unfufilling relationship,then all of a sudden, it’s terrible and she’s a terrible, and branded is the big scarlet A on her chest. There’s no understanding for her at any cost. That should most definitely be explored one day 🙂
    Okay I have to get back. Until next time! 🙂


  2. Ah… The Scarlet Letter A.

    The man’s a straight up player, a John Wayne where women are the frontier. Whether women wear it or not, it’s there where there’s promiscuity involved.

    I think one thing is the hidden sensitivity of men. We expect for women to understand our weakness. If we get cheated on, our world is crushed, and we won’t extend that same degree of understanding… I’ve seen it time and time again.

    Big Boom’s answer is so on point. His answer would be fitting for women also. I knew some girls back in the day that would brag about their exploits just as hard as my boys. We do it because it’s fun and it feels good.

  3. curiosity and a human’s inert nature to conquer – everything.

    Because its not just men that do this, but women as well. We always want things we can’t have.

  4. That’s so true Sylvia. Once we get it, we find out that we don’t want it. The problem are the men and women who know that they are just conquering uncharted territory with no plans of developing it. That makes it that much harder for a person with a true heart get a healthy relationship started.

  5. Some men cheat for the same reason a child sneaks a piece of candy. Cause it feels good! But most often it is to feed an underlying need. He may be insecure and need reassurance. He may be hurt and confused.

    Other men cheat to add another notch to their already notch-filled belt, like collecting stamps or something. These are the dangerous men. Whatever the REAL reason men cheat, it’s important to be able to understand WHY.

  6. The age old question.. Well my take is, many men cheat because of greed, low understanding of relationship worth and finally the lack of personal modeling from males they know or see.

    The idea we live in a sex charged society has made men’s greed increase. The availability of sexual charge entertainment feeds this behavior like a drug. Porn is a billion dollar business, TV is filled with the idea of get all you can and movies makes the same claims. The message is loud and clear that its OK to want all you can have because you simply can. As children young see the man with the most ladies is deemed cool. Why wouldn’t a young man want be that way when he grows older.

    Then we have the idea of a monogamy, the unicorn in many men’s minds. Men are not faced with or taught monogamy at younger ages so when they grow older they equate marriage or long term relations as “Traps” or “Institutions”. Today’s culture doesn’t promote the idea of staying in a relationship with one person it promotes stay with them until your bored and then get a new one..

    Too bad many brothers don’t catch on to leave the first woman alone before getting with the second. Hey just cheat and when caught use some lame excuse. We hear constantly the excuse of how the mistress understands me, she feeds my needs or she does things my wife, girlfriend or lady won’t do.. All weak excuses to cheat.. Where are the examples of strong relationships, strong values and God forbid the talk of “LOVING ON PERSON”.. Cheating seems to be so accepted that many don’t lose a night of sleep when its flaunted in out faces. We say mind your business or she’ll catch him..

    Finally, the role models for not cheating, where are these men? Where are the men who stand up and say strongly “Don’t Disrespect Your Woman by Cheating On Her!!””? They are few and far between. Many men are raised in homes of single parents, multiple loves or whatever. Who is there to set the example for the young men to come?? Too often we see the same behaviors passed from Father to son to grandson with no one stepping in and saying enough..

    I don’t have all the answers I can only offer what I think. I know why I gave up cheating and that came by changing my faith.. That is another blog all by itself.. Religion does work, I am proof, however nothing will stop you from cheating if you don’t see it as a negative..

    Just my thoughts on this,,

    My new book speaks on my change from cheater to man of God in poetry form.. My second book will discuss it in detail.. Its entitled “From Gigolo to Jesus”.

  7. @Barbara Grovner – Thank you for making your presence felt. I appreciate the fact you took the time to make your presence felt. And wow, you hit the nail on the head, no pun intended.

    Many times, we “think with the wrong head” and don’t take the time to understand the results of poor judgment and ignorant actions on our part. This stems from not putting a true value on the relationship that can be built with a little effort and a lot of time.

    Being married and committed is hard work. It’s definitely not all fun and games. Love runs things when pleasure just won’t get it. Cheating, whether done in marriage or courting, is an easy way out of the test that being committed poses on a daily basis.

    If you can’t marry the person that your are cheating with, then you shouldn’t be cheating… If you can marry this person, make it happen and be happy with what you are getting yourself into…

    @KL Belvin – What’s up, dude? It’s great to not only get the opinion of another male voice but even greater to get the opinion of a wise and experienced man.

    You bring up an interesting perspective. Men are indoctrinated that there is a “cool factor” in being a cheater. We see our fathers do it. We see our uncles and brothers do it. We are encouraged by our ignorant friends to do it.

    Let a young man commit to a young lady. “Uh, oh. You’re on lock down. You’re whipped. She got you in her back pocket.” He would rarely hear anyone say, “Stay true to her because he might be your wife. I’m proud of you. That’s so mature of you.” It’s just not a part of our culture as men and definitely not as Black men.

    I hope this is not the last we hear from you. Check out the other Q&A entries and shine your light.

  8. KL Bevin–thank you for sharing…that was well-spoken and received. I cannot wait to read your material in the near future, especially with a title, “From Gigalo to Jesus.” Amen!

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