I’m fit and intelligent but can’t get a date. Should I give up?

The question I’ve had some short relationships, been on many dates, and had one long-term relationship (a while ago now) where I was dumped on the day before we planned to get married. I put a lot of effort into online dating, but the final straw was sending quality personal messages to 47 different women over six months and receiving nil positive replies. I’m in my late 50s, slim, fit, tall, of average and conventional appearance, articulate, humorous and intelligent.

From hard work and living modestly, I have been able to retire and now volunteer for a charity – the task is mainly helping the sick and disabled. I also co-run a local social group for get-togethers and outings to help not only me, but others, to meet people. I discount those who are too old, those who I wouldn’t go on a see-saw with, and women who say, “Done that and got the T-shirt” about relationships – and there’s rarely anyone left.

I’ve recently dated someone who talked long-term only to end it abruptly without giving a reason. This has been devastating. We only ever hugged, but this reminded me what is absent from my cold life.

I have thoroughly disproved the saying “There’s someone for everyone.” There obviously isn’t. Should I resign myself to being alone for the rest of my days? Or should I keep trying and hoping to meet someone special, knowing that repeatedly failing is damaging to my self-esteem and my mental health?

Philippa’s answer I probably get more emails on this topic than any other. Like you they are well-meaning and proactive about meeting people. And, like you, they’ve had bad luck. I’ve been saying: make yourself vulnerable; dare to share your feelings first; be who you really are rather than who you think you ought to be; and if someone doesn’t like you, that’s about them, don’t take it too personally. But your email has alerted me to something I may have been missing. And that is, lack of success can cause bitterness and resentment to build up. You’ve noticed it in some of the women in your social group – the ones who say, “Done that and got the T-shirt” – which got me wondering whether you are wearing one of those metaphorical T-shirts, too. Could a resigned pessimism, with a side order of bitterness, be leaking out of you? When we’ve been hurt, we build up defences; but if we do that, no one can get in.

The “see-saw” comment is problematic. It sounds like you are referring to weight. This attitude may make you appear as though you are searching for a commodity to use rather than a person to relate to. People will pick up on that. Who wants to be chosen just because they’re slim? Don’t think of online dating like shopping: the perfect person is not out there. Settle for someone in the ballpark instead and when you each allow the other’s influence and dare to be flexible you just might become each other’s number one. Don’t think of yourself as just the chooser either; allow yourself to be found, too.

I expect you are a nice person. And I believe most other people in your situation are also lovely, but it’s understandable that you may be wary after having been left at the altar, ghosted and rejected – but too much wariness is no help when you’re looking for intimacy.

If the women who replied sounded negative, maybe, like you, they have been worn down by using dating apps. Perhaps that’s something you could ask the next time you use one of these apps. The counting of the messages made me laugh, but remember this is dating, not writing an academic paper – you have nothing to prove.

There’s a hint of something else that might be putting people off – and that is how certain you seem about some things. Try to keep more of an open mind, embrace more of “don’t know” and less of being sure of what people are like and whether you’d get on with them. Put judgment to one side (people can smell “judgy” from a mile off). The way you judge your appearance and character also gives me a hint that this is how you might be judging potential dates, too. No more putting people in boxes and, anyway, your type might not be your type.

Your “too old” also rang alarm bells for me. If you are only going for people younger than you, it could explain the lack of replies to your messages.

You don’t have to write off ever meeting anyone and you can still get on with the rest of your life and aim to relish it as much as possible, with or without a long-term relationship. You don’t know whether you will find a partner or not and you’ll need to get comfortable with that uncertainty. Put in less effort, go on dates and outings to have fun, and don’t treat dating like an interview or a task. Be open, be you and prioritise enjoying yourself. You really don’t know what may develop.

If you have a question, send a brief email to askphilippa@observer.co.uk

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