Male friend making stupid comments

[helpidontknowwhatimdoing]

I recently moved to a small community and have made friends with a neighbour and her husband. He is a kind and helpful man who has supported me practically and been very kind to my family.
However he has a tendency to make quite inappropriate and sometimes slightly offensive comments which are verging on homophobic. To give examples he commented recently on what a man was wearing and saying he was a bit “sissy” he also had an issue with a local gay pride event and made comments about men being effeminate.
I try to politely suggest I don’t agree with his outdated comments and views but I’m looking for suggestions as how best to phrase this without being rude.
it’s a small community and I don’t want to offend him but I also want him to stop making comments like that around me. He is in his 30s so I can’t even blame him being old and set in his ways.
Any ideas?

He is homophobic in the literal sense - scared/intimidated by gay people.
I would just state my own view when is arose and not agree.

Next time he says someone looks like a sissy or whatever just say 'well I think he looks good. Maybe you could do with a bit of a wardrobe revamp yourself?' Obviously trying to make a joke out of it. But somewhat at his expense. He clearly is very threatened by the mere concept of homosexuality.

The lady doth protest to much.

I personally would distance myself. I don't want homophobic friends

Your neighbour has some very outdated views to say the least.

what is that supposed to mean?

OP - i would just say, every time, "oh that's homophobic"

if it keeps up? don't interact with him any more. Awkward, but i find it more awkward to have to keep interacting with homophobic people. They usually subscribe to other -isms IME and i CBA with all that

It means men who go on about hating gays etc maybe doing that to cloak their own sexual insecurities.

The moment he knows you're not homophobic like him he will zone you out. you have to decide what's more important, your values or the practical help of your neighbour? I don't think you can successfully make someone not be homophobic part time or just around some people. Bigotry just oozes from them without trying.

Very cleverly put 👌

ok thanks, your "lady" reference made it look like you were having a go at OP...

ETA: before anyone jumps in, i am fully aware what the quote is and where it's from

That's ok definitely wasn't having a dig at op 👍

Depends on your relationship but I have found in the past trying to shock them a bit will make them pause.
'I didn't know that buying a pink shirt made you hungry for cock, must remember that for next time' sort of thing.

Alternatively a 'ooh you old dinosaur, must remember that if my colleague ever pops round with his husband'

As a bisexual person i do understand that you want to keep good relations and it's not as easy as saying 'fuck off' but then I'm at am advantage, I usually say something that makes it clear I'm bi and they get very quiet... they might start avoiding you but at least they'll be polite if you do bump into them (in my experience)

I thought you were going to say he was elderly...in which case I might have cut him a bit of slack...as decades ago, certain terms weren't seen as offensive...but in his thirties?! Just distance yourself a little...I don't think you should get too pally with neighbours anyway

You can't have your cake and eat it. You can either keep your mouth shut or you can offend him, up to you which you do.

Although why you're concerned with offending him I don't know, he doesn't seem particularly bothered about offending people.

I would say something like “oh you need to be careful of who you say that sort of thing in front of these days, you never know who you might offend with that kind of comment”

Depending on my mood and whether I felt safe or unsure about the reaction I might get I would use different tones of voice and eye contact to make the point