To have had enough of irritating guy

[Timetable99]

I feel partly responsible for this situation but now I'm wondering how best to deal with it.

A few years ago DP and I got involved in a group hobby where we met a guy who was socially awkward and really quiet. I took him under my wing somewhat as I know from personal previous experience what it's like to be socially awkward, I knew a lot of people in the group and love making new people feel involved, and over time he became a bit more outgoing and loud, which was lovely, and I was glad he was coming out of his shell. However we were never really what I'd call 'friends' - we'd just see each other at this hobby and have a bit of a laugh, and that was that.

However, in recent months (since lockdown has lifted especially, and since we're meeting up more regularly again) he's particularly latched onto DP and me as we tend to organise a lot of the other social events for our closer friends in the group and he isn't seemingly taking the hint to back off a bit. I've had a girlfriend complain to me that he's been "creepy" towards her (over-familiar and flirting basically), and several of our friends are fed up of him because he tries too hard, wants to involve himself in absolutely every social opportunity he hears about even if he's not been invited, and is a bit much both over text and in person. He tends to message DP and me several times a week (and sometimes several times a day, like today) asking about what we are doing and can we meet up at the weekend etc. - he seems to be pinning a lot of his hopes for entertainment on us, which is becoming uncomfortable and smothering.

How do I best manage this? I find him irritating at the moment but I don't want to upset him by being too blunt, especially if he is still finding his feet socially. DP feels sorry for him and says he seems depressed, and wants to help, but he also gets a bit fed up at times. We both work hard so our free time and energy are quite limited and sometimes we are just too tired to put in the effort with his need for entertainment! AIBU and what can I do to resolve this? I've tried backing off by not being as responsive as usual but it just seems to be making him try even harder to become close, and it's making me feel really awkward.

Bumping this for you.
It sounds like your lives are quite intertwined so all you can do is not reply unless it’s essential I would say.

Step back a bit from the organising of events, and get other people to do it. When he asks what you are doing, then you can say you have been invited out by other friends, and he can't come with you, sorry.
He'll get the message in the end.

YANBU, particularly as it seems he’s creepy when with a woman alone and you and DP aren’t there to witness it.

I think you should tell him that is being intense and you just don’t have the time to be available that much and then stop responding to majority of his texts and only reply when it suits you (e.g. once a week).

Is your friend that he creeped on ok?

I’ve had to have ‘the conversation’ a few times in life, with overly-needy acquaintances.

I usually do it by phone (meeting up gets their hopes up too much).

I say that the level of contact they prefer (x texts per week, x catch-ups, etc) is just not what I prefer. That I have many responsibilities in life (I slightly exaggerate some, like the amount of contact my mum needs, or how onerous tending my garden is). I say that their preferences are valid, and I’m sure they’ll be able to find people who match, but I don’t.
Once I had to really spell it out- that I wasn’t able to answer more than one text per fortnight, and that things were getting a bit lopsided in terms of them waiting for me to organise their social interactions for them.

If you say it gently and check for understanding, I find it generally works. Usually there’s a period of them testing the boundaries you’ve set, or sulking a bit. That is actually useful because you can reiterate the boundary, and show a bit more annoyance at that point. If they don’t settle into a more two-way routine after that I’d feel no guilt in going very low contact or phasing them out.

Helping people become more socially adept includes introducing them to boundaries. It’s not you cutting off your help, if anything it increases your kindness. And you get the bonus of some assertiveness practice for yourself, which is always important.

I’d be pulling him up on the creepiness thing too, it’s another pothole beginners often fall into. He may be oblivious, and it’ll quickly lose him invitations. You need him to get better at this stuff so he gets on with his own social life?

I agree with PPs that you need to pull him up on the creepy thing if you haven't already. It may just be a misunderstanding of social cues on his part, or he could be so bad at socialising he's trying so hard to be friendly that he's creepy. Either way, it's not your role to fix or teach him but you can use it as a good reason to step back from him. He could still be involved in the group hobby with you both but really he needs to make new friends to get more experience socialising.

You could suggest that he joins a new group, or makes friends a different way- maybe with online hobbyists? Or you can phase him out by being less and less available, answering messages less frequently and allowing him to get the hint by himself. His mental health and lack of social skills is not your responsibility, you're allowed to not be friends with someone you don't like!

Thanks everyone, really appreciate the bump and @madamemonk your points about setting and reinforcing boundaries, and practical examples, are great.

DP is annoyed with me for refusing to go out with this guy today and "help him with his depression and fix his social skills" (he suggested to the guy we could meet as a three without checking with me first!). We actually argued about it last night. He says I shouldn't be so swayed by my friend's opinion (the one who felt creeped out) as I could tolerate him better before. It's true, I could before he latched on, and what I see as freedom to decide who I'm friends with my DP sees as me being too easily influenced! Grrrrr.
Thanks for asking about my friend. She doesn't suffer fools gladly and is very disparaging of people who she doesn't approve of. She also doesn't appreciate having her personal space invaded which this guy does to everyone constantly!

The guy set up a messenger group with just DP, me, and him at the beginning of summer and posts in it regularly asking when we can meet up. I've stopped texting in there pretty much and am not sure how to exit gracefully...