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(Editor's Note, this letter was written before Doc's death in August, 2020 but still relevant as Doc's principles are timeless).

Hey Doc,

HELP! I’ve messed up a great relationship and I don’t know if I want to or should try to repair it. Here’s the story.

I started dating Sharon six months ago. She’s 50, I’m 43. She has always shown a high level (90%) of interest in me and treated me well. In fact, she asked me out first. After five great months I discovered her romantic past was much more on the slutty side than I first assumed. When I asked about her past she’d always say “I don’t like to share my history,” but at the same time she said she hadn’t dated much. Well, Doc, I hate to admit this, but three weeks ago I developed a socially communicable disease, to put it as discreetly as I can. I asked Sharon to get tested for it, and the test came back positive. At that point I asked her to be less elusive about her romantic history and came to find out she’s had 25 partners. (My own history is only three partners, since I was married for a long time, until 1998.)

It came out that most of Sharon’s liaisons were one-night stands while she was on various vacations. Her last serious relationship started in 1989 and ended in 1995. She cheated on that guy with a one-nighter in Tahiti two months into their relationship. She claims it wasn’t cheating because they didn’t have an exclusivity agreement. (To me, being intimate with someone means you are exclusive.) For the rest of the time, she says, she was faithful. She also cheated three months into her only marriage back in 1974. This revelation of her promiscuity has had a devastating effect on my interest in her. She claims everyone was playing around “since it was the 80s” and doesn’t understand why this knowledge makes me feel like crap inside. I know this sounds like how a woman would think, but I just don’t feel special anymore.

We had a big talk about how this new information makes me feel, as well as my changed perception of her. (After peeking at her vacation diary, I realized Sharon was hitting on every French guy she had any interest in during a jaunt she took before meeting me.) But I don’t know what to do.

My question is, am I being too hard on Sharon’s history? Any ideas on why this knowledge is making me feel like crapola? Is there some way of changing my perception of her back to where it was? I haven’t dated since my divorce in ’98, not that I wasn’t looking, but I just didn’t seem to elicit any interest from anyone. My looks are on the weak side (I resemble David Letterman or Tom Hanks on his bad days), but I keep myself fit and have heard more than once that I look like the guys on the Calvin Klein underwear box. The problem is that most women are interested in a cute face!

Woodsie - who hates being one of 25

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Hi Woodsie,

Of course you messed up this relationship. And the reason you did is because you haven’t memorized my rules. Otherwise you wouldn’t be in the predicament you’re in. And I haven’t even read your story yet!

So, Sharon asked you out first? I just got a nasty letter from a female saying how horrible it was that a guy waited to call her. But that girl is structured – your girl has high Interest Level. Sharon saw what she wanted and went after it. Isn’t it great, guys?

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But let’s move on to your problem. You don’t really want to know about Sharon’s past, Woodsie. Because if she tells you she’s had any partners aside from you, she’s going to be a tramp, right? On the other hand, I’ve got to wonder what section of the Australian outback you’ve been living in all your life. You’re looking for a virgin who’s a half-century old? Good luck with that! But here’s the most important point: I always tell you guys that it doesn’t raise Interest Level to talk about her past.

Now you’ve gone and contracted a socially communicable disease. You messed around and you paid. Then you went back and tried to talk about Sharon’s past again. Talk about beating a dead horse. I mean, what’s the point? You already got the disease, pal. If Sharon had only one partner or she went to bed with the entire Southern Cal football team, what’s the difference? So she’s had 25 partners -- that’s not so bad. That means she only dated a guy for an average of two years before she dropped him.

You say you’ve only had three partners, Woodsie? The real problem is that you never figured out why your wife dumped you before you moved on to a new set of complications. Like my cousin General Love would say, “Soldier, you were unprepared for the battlefield of dating!”

Who cares if Sharon’s liaisons were one-night stands? She’s 50 years young -- what did you expect? This is what you’re going to get if you date in your own age range. To you Psych majors, college girls don’t want to be adopted by old geezers like us.

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How do you know when your girl’s relationships began and ended? Would you bet your life on what Sharon’s been feeding you? All you have to know is that you got an infection from her, and I don’t care if she got it one night from one guy or from the U.S. Navy. Thank God she doesn’t leave out any of the gory details of her past!

You never asked Sharon if you two had an exclusive relationship when you jumped between the sheets with her. You can’t assume anything when it comes to women, buddy, and that’s the first thing you have to realize. And by the way, when you’re going to bed with someone, what does it mean? This lovely lady of yours could be sleeping with two guys at the same time. So you have to try and find out this stuff sooner. Remember what I’ve told you again and again: you guys have to be love cops on Love And Order.

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Sharon’s promiscuity should have a devastating effect on your Interest Level in her, Woodsie, but not because she’s been out partying with the backfield. You should only be worried about the fact that you got a disease from her. And by the way, why isn’t she visiting the doctor regularly since she’s into dating entire battalions? When she told you about her adventures in the ’80s, you should have looked at her with sad eyes and said: “But honey, you’re the love of my life and you’re only 50. I thought you were new!”

Just because your girl gave you a social disease and you found out that she likes entertaining the rugby team, you don’t feel special anymore? It really bugs you? Why is that? I don’t understand it, myself. If you wrote to an advice columnist do you know what they’d tell you? “Typical selfish, insensitive man. You’re not giving enough of yourself to your poor woman! You’ve got to be more open and show your feelings!” To you Psych majors, beg her to take more jewelry.

Why are you shocked that Sharon is interested in every Frenchman who’s ever lived? She asked you out first, remember. So when she’s in France, she’s going to be chasing after half the male population. I guess you’re not so special after all.

But in the end, no matter what, you can’t change the past. Get off it. Look forward.

You’re not being too hard on Sharon’s past, dude. You’re just stupid. You should have inquired about a blood test and a marriage certificate before you went and got yourself all diseased. So forget about her – you have a bigger problem to worry about now.

You won’t be able to erase your new perception of Sharon as a trollop. Once it’s in your memory bank, it’s there forever, and what she told you about herself was way too big – it’s like an elephant standing in the kitchen. In her defense, you kept nagging her. And like my cousin Fast Eddie Love says, “Only women are supposed to nag, didn’t you know that? It’s their divine right!”

So, Woodsie, go and memorize the Dating Dictionary, and once you’re clean and cured we’ll go out and get you someone who’s alive and breathing. And hopefully the next one hasn’t been out with a couple regiments of marines!

Next time, don’t mess with a community project.

Remember, guys: there’s an old Cheyenne proverb that says “Leave the past in the past.”