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 She is incredibly lonely and gets sadder and more withdrawn with every passing year.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?

What about researching and encouraging her to go on solo walking/ exploring holidays? Lots of groups do this.

I found local Meetup groups great for building friendships after I was widowed. But turning up at the first event is really really hard. So take PP's advice and find the most suitable sounding group near your sister, and then turn up with her, even if the time/date is not the best for you. Its a one-off you won't need to go with her to subsequent events for that group.

There are still proper marriage agencies.
I think there's one called the country register. They do all the security checks. Sarah Beeny owned another, my best friend?

I find there's lots of people looking in church groups (if she's a church goer). Widowed people of faith tend to get re married. My husband calls it recycling!

I've been married nearly forty years but still have a twinkle and find men chat me up. I'm not interested but I do love to match make.
Others have said try a new hobby and I agree.
Cities tend to have more mixed groups.

I'm going to buck the trend here, and say she should date. Which is funny, because I'm pretty much the poster girl for the friend filled, independent man free life PPs are suggesting you help her achieve.

But. It sounds like she knows her own mind, and what she wants. And when I was OLD I met many, many men just like her: wanting a relationship to provide everything- a companionship, social life etc- because they had no friends. Now I didn't like that at all, but it strikes me that they might be a good match for your SIL.

But as a grown, independent adult, surely if she wanted to do OLD surely she'd just go out and do it? (And how do you know she's not doing it already, but not saying anything until she's had a "success" or two?)

No, she WOH.

Thanks, this is interesting (if only because it contradicts what everyone else is saying!). She is very secretive, so this is possible, but I doubt it. She tried OLD about 10 years ago via My Single Friend (or whatever it was called), but there were very lean pickings in her part of the country and the two men who contacted her didn't interest her. She also saw someone she used to go to school with on there, which put her off.

The walking group idea is a good one and one I've encouraged her to do in the past. She nearly did go and join a walk at one point, but then she got invited to a family thing and cancelled, but I'll suggest it again, good idea! Perfect time of year for it too. I'll also have a browse of Meet Up groups in her area. She has interests and maybe there's one that will appeal. Another good idea! Thanks

The thing that most opened up my social circle five years ago after feeling very lonely during the pandemic was volunteering at a local community arts centre. I started off behind the bar, perhaps two nights a month and then started getting involved with poetry nights and later acting. That might seem like a leap right now, but then it did for me at the time. I met some lovely friends and when my OH turned up three years ago, I had the confidence to go for it. Baby steps are what are needed here. She is lucky to have a sister like you though.

I found that the best app was Bumble.

The thing is that she has to WANT to do it. You can put all the ideas and clubs and groups under her nose that you want, but unless she's really motivated to join them, she will nod and smile and do nothing.

Is it that doing nothing feels safe for her? She needs to push her comfort zone if she wants to meet people (not just men), but you can give her all the encouragement in the world and she won't do it if she doesn't really want to.

I agree that walking groups would be the perfect thing, but they are VERY easy to talk yourself out of attending (it's too wet, too windy, too cold, don't like the route they're doing, haven't got the gear...) so if you want to get her out there then the steps are going to have to be SO tiny that she almost doesn't notice them. Could she foster kittens or do some fund raising for CPL?

She's pushing 50, has only had one relationship in her life, has poor mental health and is sad and withdrawn. I think it could be argued that this particular ship has sailed. As things stand, she's unlikely to be able to attract a good quality partner, and is exposing herself to the risk of further heartbreak, or much, much worse.

Walking groups, birdwatching, cycling, photography, groups where there are likely to be men.
Volunteering - charity shops that sell furniture, gardening groups

Yes, this is my big worry. I think she feels that the ship has sailed too and has given up. It's so sad, because she's attractive and kind and would be a great partner for the right bloke. But getting from here to there feels impossible - there is just this huge chasm that she has to bridge to get there.

My niece is similar she's 37 never had a boyfriend or friends. She's lovely, kind, compassionate but cannot connect. I holiday with her as she wouldn't go otherwise she has zero connection with other people. She loved our ski holiday but couldn't engage with her ski group. It's hard knowing what to do. I suspect ND as it is rife in my family. She has been wrapped in cotton wool her whole life parents facilitated every aspect from job, car buying home it's like a part of her hasn't developed. I sympathise its hard seeing a person you love struggle, but equally we can't fix it for them.

My DSis is quite similar @fiwishicouldbehappier, although I don't think she's ND and she's braver and more able to do things for herself than your niece. She's always found employment for herself, travels alone, has friends, manages her life very well day to day, but when it comes to relationships she's just sort of failed to launch somehow.

Does your sister want any of this?

Would she interested in going to the gym or a walking group?

I find it a bit dismal that having ‘a man’ is the essential jigsaw piece/ the societal validation a women seems to need despite the fact she has clearly mastered everything else in life. I am concerned such societal expectations reduce her self esteem and almost create the loneliness.m and sense of failure. Please
don’t reinforce this with your well
meaning ‘help’ to find a man.

I love that she is choosy and protecting her nice life.

All lifestyles have pros and cons. Be gladshe isn’t tying herself in knots
over being left alone on Saturdays while he goes
to the pub, suspicions of work affairs, trying to balance the books with a gambling spouse.

However I would suggest you don’t feel sorry for her too much, she can be better supported by being celebrated for creating a good life for herself and accepting she is capable of finding what she needs.

OP, people mostly do what they want to do. If she wanted to date, she'd be dating. If she wanted to join a walking group, she'd be in one.

Bluntly, as you present her, she's a lonely, unhappy, withdrawn middle-aged woman who has poor MH, has had one relationship in her life, and whose 'entire world' is her cat. Does she have good qualities other than being kind -- what would she be bringing to a relationship?

This post really chimed with me, as I could almost have written it myself. My sister is mid50s and has had a few pretty OK relationships, but has been on her own now for more than 2 decades and would really like to meet someone with whom to share her life. She's attractive and sporty, and I think she'd be a great catch, and I've spent so much time angsting over how I might be able to help her.

The things mentioned in this thread (meetups, walking groups etc) are all things that we've encouraged my sister to do. However, I came to the conclusion long ago that this kind of "helping" just doesn't work, and in fact, it can be positively unhelpful because it puts the "helpee" in a more powerless position.

They somehow how to be able to grasp things for themselves and take the necessary action....which, for some reason, they find impossible to do. And we, of course, want to step in and "solve" the problem, but I don't think this is necessarily helpful, especially with things like online dating (which is something that I've no experience of).

I really feel my sister would benefit from therapy to work through all the feelings she has about her life...but if somoene said that about me, I'd feel so belittled and patronised (fyi I do think that therapy would really help me too).

So I just try and spend as much quality time as possible with my sister, and try not to "help", unless specifically asked. It's heartbreaking to see someone so unhappy though.

So many thoughtful and challenging replies - thank you! Those of you who say that if she wanted to change things, she would, are of course absolutely right. Clearly, she knows what she COULD do and she's choosing not to. I suspect she doesn't want to open herself up again to the possibility of being hurt like she was hurt before, because she wouldn't survive it. And that is entirely understandable.

They somehow how to be able to grasp things for themselves and take the necessary action....which, for some reason, they find impossible to do. And we, of course, want to step in and "solve" the problem, but I don't think this is necessarily helpful

This perfectly sums up my dilemma and also helps me to see that it's not MY dilemma at all. I love her so I want to help her, but the kind of help I'm considering wouldn't be helpful at all, it would quite possibly just make her feel worse. So I need to sit in my discomfort with that and accept that I can't help.

I know she would LOVE to meet someone, but she wants Mr Perfect wrapped with a ribbon and delivered to her front door.

I have long thought exactly this about a lovely friend who expresses how sad and lonely she is while most of us are settled down. She feels life has been very unkind to her and says it's unfair but at the same time she won't take any steps to change anything.

It's such a difficult situation to watch someone who wants something but can't take the steps towards making changes. Having said all that I did (above) about how I feel that "helping" is not helpful, I've remembered a situation where the opposite was the case. My friend had got divorced after a dreadful marriage, and had narrowly escaped getting married again to a bloke who wasn't suitable. She had decided that she was better off never being in a relationship, but another friend suggested that she give Bumble/Hinge a go (I can't remember which). And she's met the most brilliant bloke and is very happy.

However, this friend is psychologically resilient, outgoing and can take the knocks. And was willing to take the risk of taking action. I don't think this is the case for my sister, who is too vulnerable.