Dear Michael:

My best friend, Dex, is a great guy, but one thing he does really bugs me: Everywhere we go, he hits on guys. We’re both single, so I used to think I was jealous, but not anymore. Recently, we were at the same party and he was hitting on a cute young guy (he always goes for the really young ones), and it was so obvious and sleazy that I was embarrassed to be his friend. After he walked away, this young guy said to his friend: “Can you believe how aggressive that guy is? He must be really desperate,” and then they laughed at Dex. Do I say something, and, if so, how? Or do I say nothing and drop him? He has so many other good qualities, but this one drives me nuts.

Almost Done with Dex

Dear Almost Done:

It’s hard being a friend sometimes, isn’t it? Everyone has qualities that we love and a few we can’t stand, so what do you do when the bad starts to outweigh the good? Below are some options to consider.

Is there a gracious way to bring this up? To discover how, I suggest you write down what you want to say to Dex and then put it away for three days, then get it out and reread it. As you read it, ask yourself: “What would it be like if someone was saying this to me? How would I handle hearing something like this?” If it would make you defensive or pissed off, then edit it until it doesn’t.

It’s hard to talk about uncomfortable emotions, but if we can’t practice with our best friend(s), who can we practice with? Do you think Dex is willing to hear what you have to say? If you’re really close, odds are he is. You could say some version of: “Dex, I’m uncomfortable with how often you hit on guys when we hang out together. Can we talk about this?” He may be unaware and welcome your input (or not), or he may be aware and open to talking about it (or not). You can’t predict his response, so focus on what you want to communicate. Be respectful, kind and honest. Put yourself in his shoes. If he’s close to you, as you say, he will care about your feelings. What he chooses to do about them is up to him.

Another option is to not say anything but to avoid situations where this behavior is likely to occur. But if he is really your best friend and he does this “everywhere we go,” that tactic probably won’t work.

A last option is to see him less and say nothing, but this is really the coward’s way out. Have faith in yourself and your friendship, and use this awkward situation to get better at talking about difficult emotions. It’s a good life skill and, sooner or later, we all have to learn it.

Dear Michael:

As the holiday party season is starting, I dread it. Why? Because I don’t have good social skills. For example, when I’m stuck with someone boring, I don’t have the ability to short-circuit their going on and on, so I just stand there and go, “uh-huh” or “hmmm,” hoping they’ll get the hint that I’m bored. They usually don’t, and so I get stuck with the duds and can never seem to get over to the fun people I want to get to know. Any advice?

Stuck with the Duds

Dear Stuck:

I have three words for you: assertiveness, politeness and a rehearsed exit line (OK, the third has four words, so sue me). Part of everyone’s repertoire of social skills is learning how to be politely assertive with people you want to minimize time with. This is where the rehearsed exit line comes in. Let’s say you’re with Mr. or Ms. Dull as Dirt. After a few (polite) minutes with them, it’s time to be assertive and bring out your exit line(s). It’s a good idea to have more than one in your bag of tricks. Here are some possibilities:

“It’s been nice talking with you, but I’m going to walk around a bit now” or “It’s great to see you, but I need to refresh my drink/get some more food/use the restroom.”

Note that each exit line is a two-parter: The first part is a gracious thank you/compliment and the second part is telling them that you need to leave them to do something else. Try these out, and I hope you’ll never be stuck with the “duds” again.