How to help my sister safely start dating in her late 40s

[zurigo]

My DSis is late 40s, no DC, lives alone and has only ever had one (pretty disastrous) relationship. She is incredibly lonely and gets sadder and more withdrawn with every passing year. I want to try and help her to meet someone, or at the very least take down the wall she has built around herself and be open to the possibility of meeting someone. I'd like to encourage her to create spaces in her life where she might meet men and get to know them, or even try dating apps. She is so inexperienced though that I know I will need to guide and support and encourage and somehow give her a crash course in using dating sites so she doesn't fall for every married man, abuser and romance scammer out there.

The problem is that I met my DH the old-fashioned way and we've been married for 20 years. I've never used dating sites myself and I know very little about the late 40s dating scene. So how do I support and encourage her? I suppose I'm looking for resources (websites, books, podcasts, whatever) that educate about safely navigating the midlife dating scene, but also encourage someone who has knowledge of the pitfalls to just get out there and dip their toe in the water. Can anyone help?

Also it depends on your DSis's narrative, OP.

Is she 'sad sacking' - saying 'oh, poor me, I WISH I could find/meet someone/people' as though she's expecting people to come knocking on her door?

Or is she shrugging and saying 'I'm lonely but that's the way it is, I could get out there, but I don't really want to.'?

Because if it's the first then that needs tough love, but if it's the second then she needs empathy but not sympathy - she's made her decision.

Are you certain that you want your Dsis to start dating for her sake?

There a difference between being alone and being lonely.

I’d be very offended if anyone tried to help me with my love life
one of my friends has been single his whole life and I know he isn’t happy about it but has just accepted that’s how it is and I know he’d be very tetchy if someone tried to offer any help or advice on the subject

So she does want to date, is capable person, just lost her confidence it sounds like. How was the last relationship a disaster, it sounds positive, was it the ending.

She is only 50, of course the ship hasn’t sailed, has she her own thoughts on online dating etc she has shared with you?

She hasn't said she wants to date, though. She's said she'd like to 'meet someone' and for 'Mr Perfect' to arrive at her door, giftwrapped. That's the equivalent of saying that you'd like to arrive at the finishing line of a marathon, having done the training and the slogging. She's not saying she wants to run a marathon, which is a different thing.

Wouldn’t everyone, that’s why programmes such as MAFS and Love Island are so popular, doesn’t mean she not willing to put the work in.

She sounds like she'd be very easy pickings for a love scammer or other type of abuser. I really don't think OLD is at all safe for someone like that.

I think it strongly implies she doesn't. If DH were somehow deleted from my life in the morning, ideally I would like to have someone else in my life. Do I want to subject myself to the vagaries of OLD in my 50s? Absolutely not.

People who are lonely make hopeless daters. She needs to forget about getting a partner and work on getting a social life first. Take up some new and varied hobbies or activities that bring her into contact with as many men and women from as broad a background as possible. That'll create confidence and opportunities for her.

This!
Instead of thinking about what she’d like to turn up gift-wrapped -what does she offer a man?

@zurigo reading this thread with interest

I was particularly struck by your line that at 50 it seems like a collective weight of being alone or something.

I don't particularly want a relationship but turning 50 has made me wonder if I do, or something - I suspect it's a temporary thing. For some reason turning 50 has freaked me out a bit.

However, I do think it's very easy to want a relationship in theory

And the amount of sacrifices I would have to make to have a relationship... I last had one three years ago and it kind of did my head in tbh

But.... I don't really understand why you're so involved. Also, why do you think that she is so unhappy? Has she ever explicitly said it? I'm sure people are making this assumption about me.

there are other things making me unhappy at the moment and I'm probably giving off an unhappy vibe but I think it will pass.

and you don't even live nearby, so you can't help in a practical way. I don't know. I just get the feeling she should be left to get on with things.

I have never done Internet dating and I think it sounds pretty awful - but also I wonder if the way you see her is actually accurate.

Why is it 'your job' OP?

OK, I'm just going to put this out there, but are you sure it's men she wants to date? Because frankly, in a heterosexual person of that age who has been in a relationship, to never have been in any others after that is unusual. Could she be struggling with her sexuality and unwilling to tell you that?

There's is absolutely no point in giving unsolicited advice to your sister. She obviously isn't ready to work on herself and get the help she needs.
And I'm saying this as someone who was on a good path to turn out like your sister. I sought help myself when I was ready. I'm still just as introverted as before ;) but I have several good friends now, interesting hobbies and I regularly meet new people at various different events. I'm in my mid forties now and I have never been happier with my life. I'm currently single, date ocasionally but I'm in no rush to get in a relationship.

My two former best friends had similar issues as me and for a while after I got into therapy and my life started to finally change I desperately wanted to help them. I gave up years ago. I'm still ocassionally in touch with both of them but nothing much changed in their life...

@IamtheElephant you're talking as if OP sister doesn't have a life

OP has said that she has friends

And she travels and she goes out.

Apparently, she's not doing anything in a way that OP approves of though!

I find it interesting that you said you desperately wanted to help your friends. Did they want your help? And also you say nothing much has changed in their lives.... but they may be happy! I hope so.

Fair enough, but I'm going to assume OP knows her sister better than any of us do and she wouldn't start this thread if her sister lived a rich and fullfilling life. People can be lonely even if they have friends or have a romantic partner.

And I also think I know my friends enough to know if they are happy with their lives. One often said she was probably depressed and complained all the time about various aspects of her life and still does. Sadly never did anything to help herself.
The other one actually claimed to be happy but lived more and more isolated and her life was ruled more and more by fears and obsessive thoughts.

I would advise her to type into Chat gpt really specifically what she is looking for and what she wants out of life. That will help her far more than anything else as she can build up her confidence and then spread her wings when she’s ready.

Friendship meets would be better at first, we have a few in our town, all super welcoming and friendly, they are not for dating specifically though you never know. Once she has confidence then paid for sites are better than the free ones.

@IamtheElephant fair enough
I apologise for making assumptions 💐

It's just you get a lot of people on here who say they're friends with someone when they actually send a message at Christmas and barely communicate with them otherwise

I know there are people who would be very surprised by what my life is like now. Even me! If you told me three years ago that I would turn down a New Year's Eve invitation, for example, I wouldn't believe you.

A question for everyone here making the suggestion of "joining a walking club", has anyone here actually done that?

I really feel at times like it's an auto-generated response, with the assumption that walking clubs are some sort of singles clubs only existing for hookups etc, when I imagine that the reality is very different.

No, it's not about hookups at all (though I do know a couple who met at one and married) They are a good potential social group for an introverted person who like to travel (like the OP's DSis) or outdoors and they usually suit singles as well as couples. In fact Ramblers Association do good walking holidays in this country and abroad that are good (socially) for singles.

Well, a friend of mine is in one that had so many people joining for that purpose, essentially treating it as an outdoor dating hub, in the last days of Covid, that they put in something to restrict it, like you needing to be nominated by another member and doing two ‘trial’ walks before becoming a member, because it was annoying people.

I haven't RTFT but my 2 suggestions would be:

• volunteering if she has some spare time. Gives a sense of purpose, usefulness and satisfaction. There are lots of opportunities in nearly every town. Locally we have food bank, gardening for elderly/ sick people, visiting elderly, helping people with technology on Sat mornings, helping at a cafe in a church for people to have a chat/ meet others, toddler groups etc etc.

• going on an 'adventure' holiday with others. They may or may not be single people but looks great fun. (I've thought of doing it for fun and I'm married with kids). The company is always coming up on my Facebook but I've forgotten its name.