Somethin’ somethin’ on the side

A recent conversation with a guy pal was startling.

He’s a smart, goal-oriented, ethical, solid-morals, middle-class guy. So I assume he hangs out with other like-minded folks. But apparently not so much.

He shared that every one of his friends has “something on the side.” Meaning whether married or in a relationship, all of them have either a go-to booty call provider or a regular mistress/lover on the side.

I was so dumfounded I didn’t have the presence of mind to probe for more details. So I don’t know if it is true for both men and women, married and those in relationship but not married, only true for long-time relationships, or what.

So we have to make some assumptions until I get more data. We have to assume that, based on his blanket comment, that this is true for both genders, across socio-economic strata for all races in his circle of friends.


If his social circle is an indication of much of America, it is depressing. If so, politicians and celebrities aren’t the only ones who take license with the concepts of commitment and fidelity. What is commonly believed to be an affliction of those with power has now filtered down to those with the inclination to cheat, no matter what their social status.

It is not news that people from all parts of society cheat. What was shocking to me is this man’s observation that so many do so. He said all of his friends, not just a few.

What are the implications for us midlife daters?

If we are constantly suspicious, it kills the relationship. But if we’re naive, we can get taken advantage of, as well as possibly be inflicted with deadly diseases.

Does this mean that if you’re becoming serious with someone you should hire an investigator? Some do. Seems a bit overkill unless you have some evidence.

Generally, I suggest people proceed slowly. It helps you note the person’s modus operandi. If after a few weeks, you notice he only pays in cash, only wants to come to your house, whenever you call in the evening, he says he has to call you back, these are some indications there’s another woman involved.

In fact, I suggest you don’t get serious until you’ve been to his house at least a few times. Get a little snoopy. Look in the bathroom cabinets. Are there lady products and he doesn’t share the bath with a daughter? He may shrug them off as leftovers from his last sweetheart. But just notice quantities and if some have been used when you come back.

Am I encouraging you to automatically be suspicious? A little. I’ve been taken in by cheaters and in retrospect, I could have been more astute, thus protecting my heart and my health.

The key, I believe, is to be open but cautious. Don’t accuse him of anything you don’t have solid evidence of. But also don’t believe lame explanations because you are smitten. Protect your heart.


Want more of what to look for? Get your copy of Check Him Out Before Going Out: Head Off Dud Dates


8 responses to “Somethin’ somethin’ on the side”

  1. Wayne Avatar

    You have suggested how a woman catches a man cheating but not the other way round. Men rarely leave products in a womans bathroom and women are a whole lot more sneakier than men.

    So I think you should even the advise out a little! lol

    To tell you the truth for me the sure fire way to know you are the only one is to meet the persons close family. If they have the balls to introduce their permanent partner and their bit on the side to their close family (obviously if you are introduced as a “friend” then just locate your nearest exit) then that is a creature I haven’t seen before…

  2. Dating Goddess Avatar

    Hi Wayne:

    I always appreciate your and the other guys’ comments. But this site was originally designed for women sharing with women, although many of the lessons apply to both. So since I don’t date women, I don’t know the signs one might be cheating! Perhaps you could share with us what you’ve learned.

  3. Liz Avatar

    I am not real surprised at this, although I should be. Technology has made it so much easier to cheat for both men and women (texting, internet dating sites, sex sites, etc.). Eyes wide open, for sure, but there are still no guarantees. I always trust someone until they have proven themselves untrustworthy. Very good points you made, DG, about proceeding slowly and keeping your eyes open. Trusting your gut (instincts) never fails. Somehow it seems to me that if we are going through a man or woman’s things in the first place, our gut is telling us something is not right, and then we are trying to “prove” that our instinct is correct.

    This is the replacement mentality many people now have. They look at the internet dating sites and are blown away at what is out there (compared to their perhaps mundane lives). There are oodles and oodles of very attractive and accomplished men and women looking for dates. There is always a cuter, smarter, thinner, wealthier, nicer, more fit, more hair, less hair, . . . . . . (fill in the blank) person just a click away. That is the reality of life as we now know it.

  4. Richard Avatar

    “He said all of his friends, not just a few.” It is one thing to say that all men are cads, it is quite a different thing when all your buddies share their exploits. The character of your friends say a lot about the character of yourself. There is a more than insignificant risk that someone will cheat in a relationship at some time. It is entirely different for someone to make that their norm. If his friends are enabling him, then he is more likely do it. Best to stay away.

    I like what Wayne says. The more you are integrated into the other person’s life, the less likely you are being played. Have you met his friends? Family? Co-workers? Can you call his home or office? Do you spend every weekend together?

    What is more likely: 1) The lady doesn’t know the guy is using her to cheat; or 2) The lady knows she is the mistress? I would think that #1 can’t last too long (there are always exceptions, or he goes from one short-term fling to the next), and #2 is more likely.

    “I’ve been taken in by cheaters and in retrospect, I could have been more astute, thus protecting my heart and my health.”

    Seems like there might be a lot of #1’s out there. Does the relationship persist that long?

  5. lafemmeroar Avatar

    It’s a dating jungle out there. Are we all suspicious animals? Do people over 40 have too much baggage? About the “smart, goal-oriented, ethical, solid-morals, middle-class guy” with friends who cheat: do birds of the same feather flock together?

    Also, it takes two (or 3 or 4) to tango between the sheets.

    These are cliches, but there’s truth to them. Shall we investigate?

  6. lynn Avatar

    Best rule of thumb to avoid cheaters: keep a strict rule of no physical intimacy until *after* you’ve met his entire family (including kids, parents, siblings, goldfish, the whole nine yards). In this, I agree with Wayne.

    Don’t even kiss the guy until after he has introduced you to some of the people in his circle, and never ever sleep with a guy whose family you’ve never met.

    As far as cheating, yes, women are as likely to cheat as men. Especially if they are in an environment where there is plenty of opportunity. Look at the success of Ashley Madison! (Full disclosure: I live in the city noted for the highest per capita female membership on Ashley Madison, so I guess it colors my perspective that I come from the #1 hotbed of female infidelity! LOL)

    As long as you’ve met your date’s family, you shouldn’t be too concerned. If you haven’t met his or her family, you shouldn’t make any kind of commitment, and you should not get physically involved.

    @lafemmeroar – I dated a guy whose ex-wife cheated. He was EXCESSIVELY suspicious to the point of even tapping my phone as soon as we started seeing each other! I found out, because he would drop hints through references to things I had told other people on the phone, in conversations he was not a part of and I hadn’t revealed to him. It was very creepy. I can’t date someone who does that. Also, he never introduced me to his family, and didn’t seem to want to meet mine, so I let the whole thing just die off.

    BTW – infidelity is extremely common with military wives as well as deployed servicemen and women. The stereotype of the woman standing by her man must only come from the political class of society – governors’ wives finding out about love children conceived with the housekeeper aren’t the norm for the rest of society. I’ve heard that pretty much all the married women cheat on their husbands on one nearby Army base I won’t mention by name. There’s a lot of broken marriages and heartbreak, and it’s not just the guys who are straying these days.

  7. J Avatar

    Richard: I couldn’t agree with you more. The quality of a man’s friends is a reflection of the quality of a man. Sure, I think most guys still have that one friend that they’ve known forever who never outgrew his adolescence; but the people he’s closest to now will be a better indicator of what he believes. If all of his friends are still acting like they’re 20-year-old frat boys, what makes you think he’ll be any different? I think there is some anecdotal evidence that suggests that when someone in a social group gets a divorce, many more follow; seeing someone else doing it seems to give one license to proceed themselves.

    So, I would like to believe that, in this case, the prevalence of “something on the side” has more to do with his social circle being willing to condone the behaviour than an accurate reflection of society at large.

    Otherwise, I’ll have to admit that it is a problem, and won’t bother dating ever again.

  8. Darren Miller Avatar

    In my opinion it’s not everyone that cheats but if your in a social group and a couple of them start to cheat, the others, if they are weak minded and succumb to peer pressure will try it out. It totally depends what kind of group your friends are.

    And if they are cheating then I don’t believe they are with the right person. If you are with ‘the one’ then you shouldn’t want or need to be with anyone else.