butt out.

Those kind of guys are annoying. They'll practically throw themselves at you, but if you make one move, they'll be like "whoa, buddy I'm not gay" unless they are completely wasted. If you enjoy being felt up by a coworker (which may not be so bad) fine, but don't expect him to really come out. His wife probably knows (and knew). These kind of guys tend to marry women who are very controlling, it's like some kind of punishment they give themselves for being gay. It's a mess.

Excessive alcohol many times makes for insufficient erections.

@3 your profile picture is both amusing and terrifying. Like the two men it represents, I guess - one of whom is an over-the-top cartoonish buffoon with odd skin coloring and who's exceedingly more dangerous than he appears, and the other is the Joker.

@3 that sounds like a mnemonic, but I can't for the life of me work out what EAMTMFIE stands for.

He’s probably bi and not out.

Coworker + "I really appreciate your body" = not cool.

Back when I was a young and winsome Catalina, working in hotels, I was constantly hit on by married men who appreciated my boyish charms. I was always ready for a romp on the Beauty Rest. La, the memories.....

As @6 coffeepunk notes, he doesn't have to be gay. Maybe he's bi.
The one time I can recall a coworker massaging my back, it's because we were either already fucking or definitely planning on it.

Gay, bi, whatever. Either way, this guy is a closet case. Five minutes of sub-par sex, followed by god only knows how much emotional babysitting. Avoid.

"He gets blacked out messy drunk frequently at the bars. He’s in his 40s. Part of me wants to pull him aside and tell him he’s gay."

I'd consider pulling him aside and letting him know I won't drink with people who have an obvious drinking problem.

Wonder who picked the acronym.

Oh Catalina. How special to see you.
Memories, yes.
I’m a little nervous reading letters from gay men.

Someone needs to take a short film/video recording of Randy/Andy when they are blackout drunk and email it to them with the message "you have a problem, get help". Then don't go out drinking with them anymore.

It seems like DILL is not asking what, if anything, he should say, but whether he can be a sexual initiators in two different situations with (probably) closeted men who are behaving coyly or ambiguously. DILL obviously is not worried about the fact that Randy is drinking to excess or the fact that he is out partying when his unhappy wife and child are at home, because the obvious response would have been to avoid telling Randy about those evenings he is hitting gay bars. We can also presume that DILL finds Randy sexually attractive, because it is unlikely he would be tolerating Randy's touches or contemplating sex with Randy otherwise. Unless Randy is gorgeous, it is hard to imagine why DILL would be at all enticed to have sex with a 40-something, married, alcoholic man deeply-conflicted about his sexuality. If it is all about Randy's looks, DILL should contemplate how willing he is to complicate his working environment, but if it were me, I would avoid such problems. As for Andy, if he otherwise seems mature and well-adjusted, I see no problem during one of these gay bar excursion to direct the conversation to his possible interest in men, but I wouldn't press the issue, Andy doesn't open up.

What kind of office do you work in where you go out getting drunk with co-workers and getting massages from them?!

Did Dan find this letter in a bottle his last trip to NYC, that washed up on the corporate shore of Hudson Years, 50 years after the Chelsea Piers were the place closeted types went to get off before they drove home to Jersey?

Anyway, DILF, if he's a supervisor, let him give you that HJ / BJ he is so desperately wanting to. Discretely take a pic + ask for a promotion.

Delta, that’s unethical.
Why not take married guy aside and have a word to him, tell him his wife looks distressed, is there a problem? Or not. Nobody can get inside marriages and fix them up, unless those involved want to do the work.

Stop inviting him out with you to gay bars. Or any other bars. If he still manages to get blackout drunk in your presence, call his wife to see if she will pick him up or wants you to call him an Uber. Then briefly express the next time you see him that it makes you uncomfortable when he gets blackout drunk, that you’re concerned for him and don’t want to be around that, and maybe he should get a Chemical dependency eval just to be on the safe side.

Shut down the flirting and the touching. Tell him that he’s your friend, and you don’t care if he’s gay, straight, bi, or heteroflexible, but he’s married and that is disrespectful to his family unless he and his wife have an open marriage and you don’t date coworkers and if he’s struggling with liking the male body but seeing himself as straight, maybe he should see a counselor to explore that rather than putting you in this awkward position.

That seems to me to be the most ethical and adult way to handle this.

Also, stop with the bi erasure. He could be closeted gay. But he could be elsewhere on the spectrum.

Or, if LW wants to be unethical (and he does come across as a bit conflicted about the attention he is receiving), the next time guy is super drunk and handsy, he should touch his body back, tell him he thinks he has a great body too, put his hand on the side and back of his neck and pull him in close til their eyes are locked and their lips an inch or two apart and tell him that it’s a shame he’s straight because he desperately wants to kiss him right now, and see what happens.

Or, if LW wants to be Machiavellian, he and his best friend should introduce their respective curious/closeted coworkers and hang out with them together a few times, then make plans to meet them at a gay bar, text them at the time they are supposed to meet them that they are running late so the guys don’t bail right away, and then ghost them or show up really late and see what happens between them, if anything.

But really, with a marriage and jobs at stake, being an ethical friend is the better choice regardless of what this guy’s orientation turns out to be.

If you’re really concerned about Randy and his family, LW.. then piss him off.
Once children are involved, the game changes. And we need men to front other men when they see neglect occurring. The personal is political.
The other guy, none of your business.
Married guy, don’t out him to himself either. Say his double messages are too confusing, and anyway it looks like his partner is not feeling it.
Not your place to out other people. No.
Be his friend, and sort of guide him in the direction of finding out whatever or whoever he is.
His child, he has responsibilities no matter what his orientation.

I hadn’t read your comment Alanmt, so though our thoughts were opposite, our words were similar.

LW clearly enjoys the back rubs, so while he probably feels bad for the wife and kids, he clearly does not feel bad enough to stop indulging himself by letting his married coworker rub him and compliment his body.

@19 Nice of you to take a break from twisting your thin black mustache and tying damsels to train tracks to provide those suggestions :)

@15 myself "corporate shores of Hudson Yards" not Hudson Years
@17 was being sarcastic, not serious, about blackmail - which is not just unethical and immoral, but also illegal

I would say butt out, aside from shutting down the physical contact. I am wondering who is inviting Randy to these gay bars. Does he just show up? I wonder if it would be worth talking to the wife, if they are close. Regardless of Randy's orientation (gay or bi) he would appear to have a serious drinking problem and if DILF really cares about Randy as a friend, that may be the thing to address. As for Andy, I'm not sure what the problem is there. He's young, he may even consider himself to be "out" (by virtue of going to the gay bars). DILF sounds like he enjoys the drama these two provide.

Just a point of clarification: "blackout drunk" means that the person has no consciousness of what s/he is doing and doesn't remember it the next day. It isn't possible for an observer to know while the drinker is drunk whether or not s/he is in a blackout state.

So saying, "I won't drink with you when you're blackout drunk" is difficult because you don't know the person is blacked out and they are unable to tell you or to realize it themselves.
Best not to go out drinking at all with someone who has routinely gotten that drunk.

Let's go back to the original LW, who signed off "DILF." Presumably DILF is seeking permission and is DTF his sloppy mess of a closet case boss who already loves giving DILF massages. So, while the general rule is don't stick your dick in crazy... maybe the final advice should be, just make sure he ain't too drunk to give consent?

If the guys are actually getting blackout drunk, definitely video them in that state and show it to them when they sober up. That will do more than hours of discussion or lectures or threats.

Followup to 28 - getting blackout drunk hides their behavior from themselves, but of course doesn't hide it from everyone else. That is a piece of information guys like this frequently haven't figured out on their own.

I can't imagine wanting to have anything to do with this.

There are, once again, like the last letter about tools inserted in cocks, boundary issues going on here.
If this man is encroaching on the LW’s space, for whatever reason, throw him off. If the LW is getting off on it, then he’s in the game as well.
Good he’s noticed a distressed partner and child in the story.
Now what?

Great great great gay men write in.
We all do share something in common, straight and bi women and gay men, we all have to deal with men.

Ms Lava @32 - Dealing with OS men and dealing with SS men doesn't strike me as all that comparable, but I don't think we should replicate the Captain Harville/Anne Elliot debate here. I don't know that Ms Fan would say dealing with women is all that much better.

Mr Alan @18 is correct, though I do think some monosexuals are occasionally reluctant to mention that someone acting badly could be bisexual due to a thought that such a mention might appear biphobic.

Ms Lava @20 - If I had a genuine friend acting so badly, I'd presumably advise him of his accepted duties. But I do not accept a concept of there being a Gay Duty to Act as Gynocentric Police of OS Men.

I thank all those among the general company who would like to see Randy fired over this (don't tell me the headline didn't give anyone an idea before reading the letter that the answer should be GTMFF) but have not suggested LW take that route because Randy would just claim that LW made a pass at him and we all know who wins that particular battle.

This situation is about fifteen years old, if memory serves. I remember reading magazine stories about it. I'm sure most of those in the assembled company have on occasion encountered straight men who think All Gay Men Are After Them (and, for the benefit of Ms Lava, I'll allow that they are generally about as unappealing as those who think All Women Are After Them). They were usually the ones with very few if any genuine friends from Column G. The conduct mentioned in this letter exemplifies a nasty little game some straight men with "close" gay "friends" used to enjoy. They'd act as subtly available as they could while making their claiming to be straight sound like a fabrication. The goal was to extract a declaration or, even better, an outright pass, which would set off game over, a withdrawal into offended straightness, and the virtuous proclamation that gays just can't respect any man's heterosexuality.

I'll agree with Mr Savage's P.S. on this one, especially that LW's friends do not deserve to have these straight-presenting men inflicted upon them.

Re @32. And bi men.
Gay Duty Venn. SS and OS men are different Venn.
We all have a duty to call out friends, and men are men.

I suspect Randy is bi. I'm gay and I think in some ways it was easier to come out because I felt I didn't really have a choice if I wanted to find love and affection. For someone who's bi and has found that love and affection with a woman, but may want to try other things too, it can be more confusing about how to handle that. But as others have said, not your responsibility, LW.

Poor DILF, how did he get so far so fast, to the point of receiving an erotic massage from his inebriated friend/coworker, whilst carrying all of that homewrecker guilt?
I suspect DILF is most concerned with his own happy ending.
Odds are his friend and Andy have a better chances of getting one.

Delta @27, why do you presume that? I don't see any hint in DILF's letter that indicates he's interested in this hot mess of a co-worker (not boss). It's kind of insulting to suggest DILF is that desperate just because he is gay. His question is what to do about him, and the only concrete idea he's suggested is outing Randy to himself. Presumably he's wondering what the fallout from meddling in this man's personal life would be.

Venn @33: I agree with Lava. Gay men aren't not-men because they're gay. But I also agree with you that many of these issues aren't "men" issues but "dating" issues that lesbians would not be immune from experiencing. Sure, there are some relationship issues that are caused/worsened by society's attitudes toward same-sex relationships, but most relationship issues just happen because people are flawed and complex. Also, IMO, it is far less biphobic to acknowledge that bisexuals are capable of bad behaviour than to ignore the fact that we exist, so yes, the observation that Randy is potentially bisexual is appreciated.

Venn @35: "This situation is about fifteen years old, if memory serves." This letter is not a reprint. Was there a similar letter 15 years ago? Probably, because repression, alcohol and sexual harassment have been around for centuries. I don't see Randy as playing this game you describe; that is, I don't think he is a straight man making a conscious effort to see himself as irresistible to gay men by teasing them. I think he is closeted and uses alcohol as an excuse to let his queer side out. Dysfunctional and sad.

As for the massages, that seems a grey area. I call sexual harassment, but the facts that it is not happening at the workplace/official work events and that Randy is not DILF's boss may cause the "but lots of couples meet at work!" crowd to deem it acceptable flirtation. DILF seems amused, not threatened. But I'd still advise telling Randy to knock it off because he is married and closeted and nothing good could come of any returned interest.

@39 BiDanFan Huh? I am not suggesting DILF is "desperate just because he's gay." DILF is short for "Daddy I'd Like to Fuck" and is the sign-off that LW came up with himself (I assume Dan doesn't make these up). That is, to be clear, LW saying "I'd like to fuck" [the older co-worker], as in agency and not just that LW is considering the two co-workers to hook up. So I'd say it's a fair assumption LW likes the dude, likes the massages LW is getting, and also wants to hookup himself w/ the guy, don't you?

Delta @40: I do not share your assumptions. Dan has stated on more than one occasion that not all LWs make up their own acronyms, so you can neither assume that LW made his own up, nor that whoever signed the letter Do I Lecture Friends knew or intended it to have a double meaning. There is nothing in the letter itself that suggests DILF wants to fuck Randy, and I think he would have said so if he did.

Dan, if you're reading this, it might be a good idea to tell readers whether LWs or you/your editorial staff picked acronyms, because this is far from the first time readers have drawn their conclusion entirely from the signoff, even when said signoff bears no relation to the facts outlined in the letter itself, or points to a biased conclusion the LW may not share (WANTSOUT springs to mind).

Ms Fan @39 - I was not calling this letter fifteen years old, but its being fashionable for straight-presenting men to pretend to flirt with gays. This letter could have come right from magazine articles I read at the time, in which interviewed gays would describe the behaviour of a straight friend who finally tempted them into making a move.

I have never, ever, massaged the back of a co-worker

. . . that I wasn't interested in sexually.

Is it me, or does every group of gay friends filter through non-gay coworkers / college friends / new neighbors who basically take advantage of being out with "the boys" to get black out drunk and behave horrendously? I don't know if this guy is gay, but he's clearly working a lot of issues, including alcoholism. We need a blanket term for these crazy alcoholics.

Dude (and other dude on whom we don't get specifics, by extension) sounds more heteroflexible or closeted bi/pan than gay to me. And then he wouldn't necessarily be closeted, since he directly told DILF what's up, DILF just refused to accept his statement. He's in a position where he could come out, according to DILF, so perhaps it's best to take his statement at face value: he's not gay - he's primarily or mostly attracted to/interested in a relationship with a woman (a specific woman, his wife), but he also finds male bodies sexy ("appreciates") sometimes, and it sounds like this heavy flirtation does it for him. This is only confusing or suspicious if you're locked into a binary, monosexual view of sexuality. If LW came up with the signoff rather than Dan or an intern - "DILF" - I suspect LW is projecting based on wanting to fuck this guy.

@BiDanFan: From what's in the letter, you're consistently under-reading DILF's active role in the situation. First, he's SURE two of his friends/acquaintences are gay, despite saying they're not gay (or at least one of them said; apparently bi people don't exist in DILF's world?); DILF's the common factor, and the pattern is his interpretation. Second, he's all up in a situation he could easily ignore, and if he didn't want to be involved, that's a conclusion he could have reached without writing to Dan (in fact, he DID realize that possibility, since he suggests it in the letter). Third, this is one guy in each case hanging out with DILF and DILF's friends: DILF is the only connection there, so logically, DILF is the one who must be orchestrating these outings. Fourth, there's the signoff, which DILF may not have made himself, but also which he may have made himself.

This is either a stroke letter (apparently referencing an old gay trope as ven suggests) or DILF is very much looking for the advice that he should do what he wants and try to fuck one/both of these men.