Wordplay Advises the Lovelorn

“Oh, so you want to know what I think?”

Dear Wordplay,

I can’t seem to meet any eligible men where I live. I’ve tried taking classes, going to cultural events, going on blind dates, and using dating apps. People tell me I’m too picky, but when I finally like someone (which happens occasionally), they say I’m not picky enough. (Those usually don’t work out either, BTW.) Do you have any advice? —Pining

Dear Pining,

Yes. From what you’ve described, you’ve taken sensible actions that have yielded no results. You suggest that perhaps it’s the place you live in, and there could be some truth in this. My suggestion is to follow your interests a little further, to travel to places that interest you and see what happens. If you’re not ready to move yet, consider an extended vacation or sabbatical in a place where you think you might meet interesting men. Wherever you think that might be, you’re probably right.

Dear Wordplay,

I don’t know what to do. I heard some gossip about a girl I’ve liked for a long time, and it concerns her boyfriend. I heard that when she moved away from their hometown to take a job in another city, he tried to have her offed. No, seriously. That’s how pissed he was. She doesn’t seem ever to have heard this, because she moved back home, and they got back together. I’m not exactly a disinterested party, because her boyfriend knows I had a big crush on her for a long time, and I’m afraid that if I say something and it turns out not to be true, I’ll look like a jealous turd. The problem is, I heard this from more than one source, and it seems like it could be true. For years, I’ve been heartsick over it and just hoping it never happened. Should I say something to her?—Caring but Rational

Dear Caring but Rational,

I have just made the decision for you. By publishing your concern on the Internet, I’ve ensured that it will catch someone’s eye and get back to whoever needs to know. If no truth, you remain anonymous, and little (probably) harm done, but if the shoe fits—well, your conscience is at ease. What people do with the information is up to them, but I think a real friend would want someone he cared about to know. Like you, I’m hoping it isn’t true, but neither your hope or mine has any bearing on what may or may not have happened.

Dear Wordplay,

I’m a gay man who has been in a long-term relationship. My partner has a close female friend that I have lately discovered I have romantic feelings for. Neither she or my partner has any suspicion that I am bisexual. I’m having trouble disguising my feelings and really think this woman may be my soul mate. Is there any hope that if I let her know how I feel, she might reciprocate the feelings? We all get along well and have a great time when we’re together.—All But Married

Dear All But Married,

I suspect that if you make your feelings known, the situation you described in your last statement will immediately cease to exist. Since both the woman and your partner think you are gay, any suggestion otherwise on your part is likely to be unwelcome to both of them. If you really think you want to be with a woman instead of your partner, it’s time to think about whether a separation might be in order, but before you do that, try to figure out what’s really going on. Is this woman just a safe object for your feelings because you know she’ll never reciprocate them? Are you investing emotional energy in this crush to avoid facing things in your current relationship? If you really want to be with her, how likely do you think it is that she’ll throw her close friend over for someone she’s always thought of as gay? Would that perhaps be a little awkward? Lots of questions for you to consider.

Dear Wordplay,

I’m an FBI agent and have been married to my current spouse for 25 years. The spark has gone out of our marriage entirely as far as I’m concerned, though I think I’ve mostly kept my feelings concealed from my wife. She seems content with the house and kids, but I feel sometimes that I’m suffocating and don’t know how to break it to her. There are opportunities professionally for me to go undercover; for instance, I could develop a rare form of cancer, “die,” and be placed in another city with a new identity. I’m good at my job (cyber crime), and my superiors would jump at the chance to place me in another setting. I’m wondering what you think about the ethics of changing my life in this way. I’d be serving my country and getting out of a painful situation at the same time.—Public Servant

Dear Public Servant,

Wow, how selfless you are. Glad to know there are people like you out there. I suggest, though, that using your job to end your marriage is going about it in the wrong way. If you really want to get out of your marriage, consider a trial separation, and then if you still feel the same way after, say, a year, ask your wife for a divorce. You will both feel better for the honesty. A spouse of 25 years deserves more than a fake funeral.

Dear Wordplay,

I fell in love with a woman after I spied on her while she was skinny-dipping in a hotel pool. I don’t really want to go into the whys and wherefores of how I happened to be there, but seriously, I was caught off guard. What I mean is, I was watching her from my window, and I didn’t know she was going to take her robe off, but she did, and I haven’t been the same man since. I have reason to think that she might one day return my feelings, and I just want to know—am I obligated to tell her what happened? I mean, actually, I was following her, and it’s kind of a long story, but . . . The problem is, she’s a big privacy advocate, has given lectures on it for the local university, has made it known in no uncertain terms what she thinks of spying (in a general way, not as it relates to skinny dipping). She’s practically a Fourth Amendment scholar.—Trying to Do What’s Right

Dear Trying to Do What’s Right,

1. Do you, by any chance, have any connection to the public servant in the previous question? There just seems to be an awful lot of spying going on.

2. Ha, ha, ha, ha, ha!

Dear Wordplay,

I feel like this fellow I don’t know well is trying to let me know that he likes me. A story got back to me that he happened to be looking out the window when I took a 2 a.m. skinny dip in a hotel pool while on vacation years ago. It’s kind of an odd story, but I have no reason not to like him. The funny thing is, I know what he looks like without his clothes on, too, though I’d rather not go into that part of it. Do you think there’s any possibility that something that started out like this could have a future? Technically, he was spying on me.—This Will Sound Strange, But . . .

Dear This Will Sound Strange, But,

I may have to erect an ethical barrier here. I’m starting to feel like the Wall in Pyramus and Thisbe. To answer your question, I don’t really see a problem based on what you’ve told me so far. How many people get a chance to check out the goods, not to put too fine a point on it, before they’ve even had dinner-and-a-movie? And technically, you waived your right to privacy by taking your clothes off in public, although I’ll grant you, most people would expect to go unobserved at that hour of the night. For the future, I suggest that you try to meet sometime when both of you have your clothes on. I am kind of curious as to your side of the story, but I’m too much of a professional to take a prurient interest in something that’s none of my business.