I've been nice and seem to have got myself into a situation

[Oldromance]

Old school friend, haven't seen more than twice in 35 years, partly because he's been overseas for most of them.

He's back following a series of personal tragedies, a really awful time which I won't share here. If I was a cynic reading this, I'd be wondering how much is true it's, but I know most of it to be factual and have no reason to disbelieve the rest.

Anyway, we ran with the same crowd at school but were never particularly close friends. Have a couple of niche interests in common so occasionally comment on each other's SM. That's been the extent of it until recently.

As he's back and sad, I invited him out with a group of friends, some of whom he knows, and he's invited himself to come to something I go to regularly that's connected to one of the interests. That's fine, I take lots of different people.

However, he's messaging me multiple times a day and the messages are full of innuendo. I think he'd say that just the way he is (and tbf he's been in a country where PC hasn't really happened) but it's making me uncomfortable. So much so that I've invited another male friend to join us at the thing.

I know I need to not be a wimp and step away, but....

Just block him or mute notifications permanently and don't be readily available to socialise with him.

Block him, you don't owe him anything.

Tell him clearly that you are not interested and he must stop the innuendos immediately or you will block him permanently. And do that if necessary. This is not a time for 'niceness'.

He's taking advantage of the situation and he can't be that upset regarding his personal tragedies if he's angling to get his end away with you. Cheap behaviour. Bin him off.

Just message him in response "WTF are you talking about? Why are you talking to me like that?"

Reply with the gist of this, but using a better form of words that makes you sound like an adult rather than a 14 year old!

“You’ve either got the wrong idea or you just like using a lot of innuendos. Either way please stop using them with me.”

Or just ignore him completely. He’s being creepy, inappropriate and crossing boundaries with you - without a thought of you as a separate, sentient human who might not want those kinds of advances. He doesn’t care. So just drop the rope.

No more being nice to your own detriment.

@1SillySossij I am looking at your username and laughing at your advice now! To be honest I don't think he is worth the longer more complex reply. He has shown himself to be a dick and I wouldn't be interested in meeting up with him.

Tell him how the innuendo makes you uncomfortable, and assert your boundaries.

Oh I dunno, I think the directness of it is probably what he needs to hear.

He’s probably messaging you multiple times a day because he’s lonely, but it doesn’t make it OK, much less the fact that his messages are making you feel uncomfortable. Just delete and ignore his messages, and stop inviting him to things.

Ask him to stop as it makes you feel uncomfortable

just ignore him completely.

This.

He knows he's making you uncomfortable, that's why he's doing it. Calling him out on it will just give him a thrill because you'll confirm he's making you uncomfortable. Block him. Let him go to events on his own, don't invite him anywhere else.

Just back away.
Say nothing.
He will deny it and is doing it in such a way that he can deny it.
He is a creep and also a chicken.

Your instincts are right. Just back away.

If you want to give him a chance, do this

but what are we talking here, a man in his 50s? He's not doing it because he's not learned how decent humans behave. He's not a teen boy.

He's doing it because he finds it funny. Upsetting you amuses him. Why do you want to be friends with him? I know people act out after trauma but this would be an oddly soecific way of doing it

and i wonder if he is telling the truth about what he's been through

Good advice here, however if the OP is ‘too nice’, as she describes herself, she might find the direct approach to confronting. Whilst I agree she should have no difficulties in calling this out, practically, some suggestions of how to do this more ‘softly’, might help the OP more.

OP perhaps you could not attend the event you have planned. That seems to be your last planned contact with him, so after that, you could not respond to messages or respond after a few days with vague response, helping to create space and distance in the relationship.

Text 1:
Hey John, regrettably, some thing has come up and I can’t make the concert/bike convention/lego exhibition anymore. Apologies for putting you out, as I appreciate you can’t attend anymore either. [Or, Happy to send you your ticket and you can go yourself, if you like]. Hope all is well, Joan.

He then sends some replies, possibly with innuendo. You ignore for at least 24 hours, then respond with:

Hi John, Sorry, for the delay in getting back to you. Have a bit going on right now. Will respond properly later.

Then wait at least 2 days before another response (only if he texts back), and just keep it vague, busy and drop off

You haven’t seen this person in 35 years and you’re going to make him control you. Cmon, your a big girl, tell him to back off cause you don’t him anymore. 35 years is along time. Unless you want him to be interested then it’s a different situation but don’t let him make the rules. This is under your control and PC has nothing to do with anything. It’s your dignity and choice.

He’s a creep. Just block him.

If he's a real creep, and you think the innuendo is because he actually fancies you and thinks you are available, then you have nothing to lose by being blunt.

If you think that he might actually be OK but needs to be called out on the innuendo stuff if it has become a habit, you could frame it as 'a word to the wise, X, it's not the 1970s any more, and things have moved on a bit in the UK. The kind of comments you are making/language you are using just aren't acceptable over here these days. Maybe tone it down a bit if you don't want to upset people and get into trouble.'

Just be incredibly blunt. Eg.
"Re your last text. I'm assuming you are coming to the groups I go to to create a new social circle? So I thought I only fair to bring it to your attention that a lot of your communication by text etc are coming across as somewhere between creepy and sexually predatory.
I'm giving you the benefit of thinking that you haven't realised the language you have been used to using in "whatever" country is really not acceptable here and now. In fact It will probably hinder you getting to know new people quite a lot."

Oops I see i have x posted with solo sofa.