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 She is incredibly lonely and gets sadder and more withdrawn with every passing year.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

Dating would be disastrous.

A man doesn't solve problems. I would encourage her to work on herself, join groups she is interested in, build friendships, make a happy life.

She already has had a bad relationship, starting one when she isn't happy in her own skin will only lead to heartbreak.

As someone who has used dating apps for a few years in my 40s I would have to suggest that expanding real life social circles is a far better way to meet someone. Having a wall up already then being dashed on the rocks a few times by online dating in 40s is not going to make her feel any better

I think the other posters are right here. Dating if you aren’t savvy and ‘street wise’ would be a disaster so much could go wrong. She should join groups and improve her social circle and try and widen her net that way

I agree with everyone else. A partner is the icing on the cake. She needs the cake first - some social life, some friends, some outside interests and confidence.

Being so isolated and sad makes your DSis very vulnerable and some abusive men can sense that vulnerability in women and are attracted to it. Dating is the last thing she needs to be trying right now.

Dating would be an absolute disaster for someone in her position. There’s but a single chance she wouldn’t be spotted a mile off by someone who can take advantage.
why is she lonely? Can you pinpoint why, and then address that. I say that because I’m not lonely at all, and I’m single, I have friends, hobbies, and at home I’m at peace and don’t want anyone there.
so pinpoint when she’s lonely - at night? Then take up a hobby at night. Or have a friend over.

Okay, you're all saying what I feared, which is that online dating is a shark's feeding tank and will just crush her even more. That would be an utter disaster, as she suffers from poor MH anyway.

In a way though, that makes my job a bit easier, because I do know about joining things and making friends and getting out there. However, this is advice I've been giving for her for years and she hasn't taken it. She can be very brave - she travels alone several times a year - but when it comes to social situations or going out alone to something local she doesn't do it. She has friends, so she goes out, but it's 'meeting one friend for dinner' type socialising, not the type where she is expanding her social circle and the only parties and events she goes to are family ones sigh

A walking club? Volunteer at local garden or stately home? Local history group, restoration society? What does she like doing?
Agree expanding your world and meeting new people is a good thing, but it doesn’t have to be nights out in town if that’s not her thing.

Age with others that until she is happy in her own life it would be disastrous to try to do online dating.
She needs to make an effort to find something she is really passionate about that genuinely absorbs her and it is just the icing on the cake if she meets someone, but until she is comfortable in her own skin she is too vulnerable.

It sounds as if she's a proper introvert. Introverts do like to socialise but only one person at a time. But even an introvert needs to step a little way outside their comfort zone now and again to avoid isoltaion. Usually introverts do better in groups that are based round a regular shared activity, like a walking group, or a craft group, where you are all doing something with time to talk if you want to. It's kind of up to her though, you can't do it for her.

Stay clear of OLD! Get a cat for company!

Seriously though, encourage her to go to some group social events, Meetup is a good starting point as are local walking groups. OLD is not the place for someone feeling insecure or sad.

why is she lonely?

This is a bit hard for me to answer, so I'm just going to have to take a best guess. At the beginning of her one and only relationship she was the happiest I've ever known her. She felt loved, cherished, she had someone to do something or do nothing with, she didn't have to always go home alone, she didn't have to turn up to things alone, she had someone to go on holiday with, make plans with, a future and things to look forward to. He was very outdoorsy and she loved doing the things they did together, but now she has no one to do those things with. Her friends are nice, but they don't have much time for her, because they're all in relationships themselves. So she often spends her weekends alone. She is also an introvert, so she needs a certain amount of time alone to recharge her batteries, but she is always alone and I think it just weighs heavy on her now, after nearly 50 years.

I could see anywhere where it mentions the OPs sister wants to date. When I was in a similar situation, the last thing I wanted or needed was a relationship.

Get a cat for company!

She has one. He's her world.

It sounds more like you want your sister in a relationship. What has she actually said? Just because you’re married and do things together doesn’t mean she necessarily does???

No, she does. I wouldn't be hoping to help her meet someone if I didn't think that was what she really wants, above all else. I know she would LOVE to meet someone, but she wants Mr Perfect wrapped with a ribbon and delivered to her front door.

I would recommend she build female friendships and community over dating. That will not only be safer and more fulfilling but more stable too and it will help with her self esteem too.

That's unrealistic, and I wouldn't encourage it. She might have been relying on her partner as a kind of social buffer.

I'm not sure what you can do to help. Maybe you could ask her to chum you along to an activity that you both enjoy and might be good for her? "DH doesn't like walking/is too busy but I'd like to give this group a go, could you come with me?" then hopefully once she's used to it she'll start to go by herself when you can't make it.

What happened in her previous relationship and how long were they together? She needs to get to therapy to work through things herself and why she is unable to form and sustain a relationship - there's nothing you can do to help her. If you read back your thread title it makes your sister sound like she has some disability or is very young or needs to be wrapped in cotton wool -or has something 'wrong' with her - why is that do you think? Is it the way you and your parents treated/treat her? She is a fully grown adult and doesn't need molly coddling.

Yes, she has a FT job.

Unfortunately, I don't live near her or I would.

Wise words @Owly11 I can see you read between the lines of my OP very well! And I know I can't really help her, I just want to encourage from the sidelines really, because it breaks my heart to see her so lonely and unhappy, but I've been doing that for years already and it makes no difference.

Even if I didn't have a job and a family and not a lot of time, that's not going to solve her day-to-day issue. She has a sister, but that doesn't mean she isn't lonely.