We’ve all been there. A good friend is dating someone inexplicably awful and you’re not sure how to handle it. Do you tell them? Ignore it? Leave subtle clues like creating a new JDate profile for them? Or do you write a column exploring the issue, hoping they happen to read it?

When I was in college, I dated a girl for a few weeks. She was sweet and pretty, but not all that bright, and I finally got tired of explaining things to her. The day I realized it was over was when we watched a movie that had a surprise twist at the end. I was blown away, and she had no idea what had even happened. Oops.

When I told my friends I’d ended things with her, there was a unanimous sigh of relief, and a collective “we were all wondering why you were with her in the first place.”

At first I was frustrated that they didn’t tell me and save me the trouble. Then I realized I probably wouldn’t have listened to them anyway.

When you’re dating someone, it is hard to believe your friends’ poor opinion of them comes from anything other than being misinformed. A common refrain is “you just don’t know her like I know her.” Sure – biblically.

Your friends don’t ALWAYS know what you’re looking for in a partner, and many people are much better one-on-one than they are in groups. But most often your friends are right when it comes to who you date, because your friends can judge your boyfriend or girlfriend without potential nudity distracting them.

Her pretty face was why I dated that sweet-yet-dim girl in college. I’ve made that mistake more than once (I’m sure we all have). We let physically attractive people get away with WAY more than we would allow from someone who looks a bit more Plain Jane. It’s evolutionary – big bosoms and broad shoulders make for a good gene pool. Not in the same person though; that could be creepy.

In my case, I was with someone boring and not that bright – which is a waste of time, but not detrimental to my well-being. In a much worse situation, I currently have a friend who is dating a guy who is awful in every way and yet she’s still with him, and I’m not sure what to do.

Some people look for a nice guy, but he says things like “I wish you looked more like Eva Longoria,” and “It’s a good thing you found me because you’re not getting any younger.” Some people look for a trophy mate, but she’s beautiful and he’s 20 years older and out of shape (unless you count the shape of a pudgy bald man). Some people look for financial security or ambition, but she is a well-educated business woman who makes more money than him – mainly because he lives off his parents…at 46 years old! Real winner, huh?

I introduced my wife to the crappy couple without prepping her, to see if I was just being too harsh. Maybe my standards were too high for anyone who dated my friend? Nope! Despite just a few minutes of conversation between them, the words my wife later used to describe him are not repeatable in this column.

I tried subtle methods. I tried showing her pictures of my wonderful single friends and talking about how wonderfully single they are. I tried having my wife talk to her about how great it is to find a guy you truly connect with, while clearing her throat. I even tried commenting on his most obnoxious Facebook posts so that they’d reappear in her news feed and remind her about what a creep he is. Maybe I’ll just set up a Google Alerts™ for her with the phrase “inexplicably awful” so she gets this column.

She’s begun talking engagement, and that terrifies me. How do you celebrate the union of someone wonderful and someone awful? Should I congratulate him, and give her my condolences? I guess I can ask anyone who went to Sandra Bullock’s wedding how they handled it?

I am close to done hoping they break up on their own. It can take a long time before someone realizes that their boyfriend, girlfriend, or even spouse was a terrible choice. How long did Tina Turner stay with Ike?

If my friend does get engaged, I’m going to have to tell her how I feel. Could it end our friendship? Yes. But I care more about my friend than I do about our friendship. If she has to get mad at me and cut me out for a few years, that’s a risk I have to take. The other risk is them getting married and having children that turn out to be half wonderful human and half evil robot. And as cool as cyborg babies sound, it’s not happening on my watch.

If my next column is about how I was wrong and you should shut up and let your friends make their own mistakes, you’ll know what happened. But hopefully it will be all about how I have this awesome friend who really cares what I think about people she dates – and how she is recently single.

Steve Hofstetter is an internationally touring comedian who has been seen on VH1, ESPN, and Comedy Central®, but you’re more likely to have seen him on the last Barbara Walters Special.

*Comedy Central is a registered trademark of Comedy Partners, a wholly-owned division of Viacom Inc.’s MTV Networks.

  1. Steve,
    I can’t believe you don’t know this but it is very hard for a decent woman to find a man that is her age and knows how to make her happy in bed. Your friend is not with this guy because he has money – you already said, she can support herself. She isn’t with him for his intellect – she has you and other friends for that. She can always have a nice dinner with good conversation with her friends. But the most important thing that you can’t give her, I am sure this guy you don’t like, is giving her lots of, before she gets out of bed in the morning, to go to work. Men need a pretty face, women need more than the face. What you need to do, Steve, is give a lesson to the single men who don’t understand why they can’t buy love. they need instructions in the bedroom. I’m serious. Women learn all this from Cosmopolitan magazine before they walk out the door. The magazines for men don’t teach them anything! they give them the pretty faces. Your next article should be asking all your single women friends how many men really know what they are doing in bed! I know what the answer will be. I’m looking forward to reading your research. thanks

  2. Thank you for writing this. You did a great job of expressing what so many of us are thinking.

  3. From experience, I can tell you that telling the person how you really feel about her partner is not the way to go. I have been in the same situation twice. The first time I told my friend how I felt just before she was planning to get engaged, and I lost a friend. The couple is divorced now, but no amount of reaching out on my part has been able to mend what was broken. I suppose she doesn’t want the evidence that she had a choice and made the wrong one to be around her all the time, and I can’t blame her. I miss her, but if our situations were reversed I believe I would have acted much the same as she.

    So when the same scenario arose with another friend, I took the other route. I smiled and congratulated her and was in her wedding party. We drifted apart, mostly because I didn’t like spending time with her husband. But two years later when she got divorced (because yes, you’re right, a person’s friends are usually better judges, and so these marriages will generally end in divorce) we rekindled our friendship and it is as strong as ever. Once she asked me if I knew it would end badly and I told her of course. She thought for a minute and then said that it was a good thing I never said anything, because she would never have spoken to me again, no matter what a jerk her husband turned out to be.

    I strongly urge you to keep silent and let things turn out as they will.

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