Dear John: Haunted By Hook-Up At His Kid’s School’s Drop-Off

Someone bound to remember a regrettable hook-up, a friend who can’t take criticism, and an ill friend who guilts people into getting what she wants.

This article originally appeared at GoLocalProv.com.

Dear John,

I have a young child who just started school this year. I noticed a particular woman at drop-off and pick-up time and scoured the school directory until my fears were confirmed: she is a woman I went to college with about twenty years ago. We had a drunken, regrettable one-night-stand that I know for a fact she felt really bad about later. (We had a couple of mutual friends.) We spent the rest of that school year trying to avoid each other, and we never spoke again. Never even saw each other again until now — and now we’ll obviously be seeing each other regularly. I have no idea if she recognizes me — I look a lot different now — and I have no idea what to do. Should I say something just so we can clear the air? Pretend that we’ve never met? She hasn’t given me any indication she knows who I am — what if I only serve to remind her? Every day I’m afraid my son will come home from school asking for a play date with her son. Talk about awkward. What would you do?

Signed,
Young and Stupid

Dear Young and Stupid,

Even if this woman hasn’t recognized you, there’s always a chance she will — your paths will continue to cross for years if you have young children at the same school. Though the incident happened decades ago, you never had a chance to resolve it. Now you do, and I think you should take advantage of it. The best way to prevent these types of things from hanging over your head forever is to cut them down yourself.

As difficult as it will be, when the opportunity to approach her presents itself, do so. She may remember you, or you may have to prepare yourself for an excruciating moment when realization dawns on her. You’re vague about what made this experience so unpleasant, but I get the impression that it was somehow worse than your run-of-the-mill ill-advised hookup. If you owe her an apology, it will be your chance to offer her one. It’s impossible to say how she will react, but it’s a safe bet that you will feel better once you don’t have to worry about this every time you see her.

Dear John,

How honest should you be when someone asks your opinion of something they’ve done? I have a good friend who asked me to read a play he wrote. He worked for a long time at it and he hopes to sell it, so I felt like I owed it to him to give him my honest opinion: it was terrible! I wasn’t that blunt when I gave him my feedback, but I did offer many specific suggestions on how to make it better. Long story short, he was defensive, said my judgment was “atrocious,” and has been extremely cool towards me since then. Now I’m mad at him for being such a baby about it. Does he think he can be a professional writer with such a thin skin?? How do you deal with someone like this?

Sincerely,
Critic

Dear Critic,

Sometimes people are looking for sincere and frank feedback. And sometimes, they just want to hear, “That was great! How’d you come up with that?” It’s up to the person being asked to determine which one it is.

In general, I have to be pretty sure someone really wants to know what I think before I offer much criticism. Specific circumstances can guide you, too: if the manuscript is already on its way to a prospective agent, publisher, etc., what’s the point in going over all its shortcomings? The writer will find out soon enough. When the rejection comes, you will have another chance to point out that maybe this dialogue could have been handled a bit more delicately, perhaps this plot point was a bit contrived, etc. (And let’s be honest — our own judgment is far from infallible, too, right? There’s always the chance the agent or publisher will love it.)

You’re absolutely right that anyone who aspires to be any kind of professional artist should expect to hear criticism. But if their work is inferior, inevitably, they will hear it. They don’t need to hear it from a friend unless you’re absolutely certain they want your honest opinion.

Dear John,

I have a problem that makes me feel wracked with guilt for even describing it as a problem. I have a dear friend who suffers from a serious, chronic illness and has had it for years. It will never get better, and frankly, it will probably take her life one day. It’s that serious. My problem is that I feel like she sometimes uses her illness to get what she wants. I try to help her as much as I can (her condition impairs her mobility), but I have a family of my own and sometimes I can’t drop everything to take her to the store, to Mass, etc. And then she goes into a long speech about how she understands, she wishes she didn’t have to inconvenience everybody, her condition is bad enough but to think of being a burden makes it so much worse … I usually just give in and do what I can just to end to the melodrama. But then I feel mad at myself AND her. When someone needs your help — REALLY needs it — how do you know where to draw the line?

Sincerely,
Mad, then Guilty

Dear Mad, then Guilty,

It’s a terrible shame your friend is in such poor health, and I would make every effort to give someone in her position the benefit of the doubt. But being seriously ill doesn’t give her the right to take advantage of you. And that’s what she’s doing.

She is very lucky to have you to help her cope with what is undoubtedly a tremendous burden. But your family needs you, too. You don’t have to feel guilty about that. You should explain to your friend that you truly want to help her, but if you say you can’t do something, it’s only because you really can’t. She will undoubtedly try to make you feel guilty — that’s what she does. At this point it’s up to you to say you simply can’t do whatever it is she’s asking. And be firm in the knowledge that you’re not unwilling to help, you’re just unwilling to be taken advantage of.

Since your friend is chronically ill, I am assuming she is under some kind of medical care or supervision. Perhaps her doctor’s office could help her find a social service agency or volunteer group that assists people with her condition. If she’s a churchgoer, she should reach out to her parish for help as well.

I have no doubt that she needs the assistance she is asking you to provide, but she will be better off if she has other options when you are unavailable. And go easy on yourself — you should be proud of what you can do for her. There’s no reason to feel guilty for what you can’t.

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Photo credit: Flickr / woodleywonderworks