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Over 40, never had a boyfriend or any sexual experience

217 replies

ForPoliteRaven · 07/06/2025 12:43

Exactly like the title says. It’s not for lack of trying. Online dating didn’t work for me despite having good photos and a professional writing my profile. I had a few first dates as a result, but they weren’t interested in another after meeting me. I’ve had friends try to set me up, but they weren’t interested. I was nice, their words, but apparently I wasn’t worth getting to know. My mother even handed out my phone number to a few guys over the years. I went out with them too, but the looks on their faces told me I wasn’t what they expected. So, less than ten first dates ever, and never a second.

I chalk it up to my appearance. I was diagnosed with a skin condition when I was little and I was relentlessly bullied throughout middle school and portions of high school. I had very few friends and really no family support to deal with it. I was just told to ignore them. That advice doesn’t work. I was always compared to my younger sister throughout childhood. All I heard was how pretty/beautiful she was. No one ever said that about me. I didn’t have dates for dances or the prom. I didn’t get invited to parties either. My self-esteem was destroyed before it could even appear.

Seeing my friends find boyfriends, getting married, and hearing about their sex lives hurts. I have nothing to say in conversations about these topics because I haven’t had these experiences. One of my friends even made fun of me for reaching the age of 38 a virgin and never having a boyfriend. I dropped her like a hot potato. A mutual friend has said she hopes I can forgive her one day, but she made me feel so small and like less of a woman.

I’ve been to counseling and it hasn’t helped. I was told to write down the qualities I like about myself and carry it with me so I can look at it when I’m feeling down. Another told me that I should try meeting people at church. When I told her I’m an atheist, she tried to convince me I wasn’t, and that I should go to church. I started seeing a new counselor, but I can’t afford my copays at the moment. I’m off for summer break, so my finances are carefully budgeted until I get my first check in August. I really liked her too.

What else can I do? I’m educated, kind, funny, and have a lot of interests and hobbies. I’ve changed my hair, my clothing, got my teeth fixed, and I take care of myself. I think I have a lot to offer a man. But they don’t seem to want me. Is there any hope for me? I’m so touch starved and am craving that kind of romantic touch I’ve never had before. Even a hug from a man would be nice.

OP posts:
ForPoliteRaven · 07/06/2025 14:12

hjhjhjhjhj · 07/06/2025 14:04

I really think you have to give online dating another go. I saw that there was a new dating app that skips the chat and goes straight to a date if you match. I can't remember what it was called, but you could google it and get stuck in! Just go on lots and lots of dates. You will click with someone at some point if you go on 5 dates a week!

And think of it as you being in control. You are interviewing for a partner! And also accept that there will always be people who don't like you - just as you won't like everybody. It's just life.

Finally, like others have said, I am sure you are lovely and attractive and that it's just your self-esteem that is holding you back.

Good luck!

I prefer to chat with people for a bit before arranging a date. Jumping right into it makes me uncomfortable because of my situation. I’ve considered giving online dating another go, but I’ve been so unlucky with it that five dates a week probably won’t happen.

OP posts:
Lovemyassistancedog · 07/06/2025 14:21

I'm going to approach this from a completely different angle.

Do you like dogs? Could you get one? If it's right for you, you'd potentially (with the right one) have lots of cuddles and they are a people magnet! You'd get talking to people when you're out walking in your neighbourhood and they bring so much happiness. I think you'd be more likely to attract a partner if you radiate happiness (my dog has this impact on me).

Rainytoday · 07/06/2025 14:26

You say you have had less than ten dates. That’s not very many. Keep going!

Also good idea re the dog.

CoffeeFroth · 07/06/2025 14:27

It sounds like a mixture of low self esteem and others being put off by your skin condition. Online dating is brutal and often very looks based.
Are there specialist groups or dating sites for people with the same condition or stigmatising conditions in general?

ForPoliteRaven · 07/06/2025 14:29

Lovemyassistancedog · 07/06/2025 14:21

I'm going to approach this from a completely different angle.

Do you like dogs? Could you get one? If it's right for you, you'd potentially (with the right one) have lots of cuddles and they are a people magnet! You'd get talking to people when you're out walking in your neighbourhood and they bring so much happiness. I think you'd be more likely to attract a partner if you radiate happiness (my dog has this impact on me).

I love dogs and animals in general. I have two cats and love them dearly. I get lots of cuddles and head buts from them. I’ve always had pets, and while they’re wonderful, I still feel a void. Like something is missing.

OP posts:
ForPoliteRaven · 07/06/2025 14:30

CoffeeFroth · 07/06/2025 14:27

It sounds like a mixture of low self esteem and others being put off by your skin condition. Online dating is brutal and often very looks based.
Are there specialist groups or dating sites for people with the same condition or stigmatising conditions in general?

I’ve looked online and haven’t found any. My condition isn’t too bad these days, a spot here and there. But you’re right, my self-esteem is very low. I’ve never had any really because of the way I was treated growing up.

OP posts:
Lovemyassistancedog · 07/06/2025 14:31

I understand and I'm glad you've got your cats, at any rate.

ForPoliteRaven · 07/06/2025 14:32

Lovemyassistancedog · 07/06/2025 14:31

I understand and I'm glad you've got your cats, at any rate.

Me too. They certainly keep me on my toes.

OP posts:
Justwrong68 · 07/06/2025 14:39

Love of music is the best way to meet people. Especially something specialised like jazz, try to find a community with a similar passion. Not salsa or other fads, a real passion.

CoffeeFroth · 07/06/2025 14:41

ForPoliteRaven · 07/06/2025 14:30

I’ve looked online and haven’t found any. My condition isn’t too bad these days, a spot here and there. But you’re right, my self-esteem is very low. I’ve never had any really because of the way I was treated growing up.

Edited

I'm not surprised that you have low self esteem considering the way you have been treated.
What about concentrating on improving your social circle and getting to know men without the pressure of dating.
Have you ever asked any of the men for feedback after your dates?

ForPoliteRaven · 07/06/2025 14:43

Justwrong68 · 07/06/2025 14:39

Love of music is the best way to meet people. Especially something specialised like jazz, try to find a community with a similar passion. Not salsa or other fads, a real passion.

I’m into rock music and artists like Lindsey Stirling. We used to have a bar/nightclub that catered to rock music, but it didn’t last long. My area has slowly been trying to cater to families. I’m in a conservative state, so that has an influence here. I’ve been looking everywhere for similar places/events, but there aren’t any.

OP posts:
MoominMai · 07/06/2025 15:02

@ForPoliteRaven have you tried any activity groups like walking/hiking or if you’re into history any local history societies. I understand you as I was in a similar boat not so long ago. I found someone from one of these groups and I too was v inexperienced. Tbf I had had 2 mini relationships but they didn’t involve sex. I’m single agin now and an introvert also but once I’m up to it this is probably what I’ll do. I feel you on the OLD aspect, it’s just awful in y experience like ruins your confidence more so so I vowed to never ever use it again and been over 15 years and I haven’t. All the best in your search ♥️

ForPoliteRaven · 07/06/2025 15:03

PerkyGreenCat · 07/06/2025 13:49

There is something about you that is putting men off - do you have a trusted friend who you can rely on to be completely honest with you?

Could you perhaps get a friend to arrange a double date? They could see what you're like on a date and give you some feedback afterwards.

I’ve only told three friends about my situation. One of them was the one who made fun of me a few years ago. They say nothing is wrong with my appearance and that they don’t know why men aren’t interested in me. They try to tell me sex and relationships are overrated and I’m not missing much. They don’t have any single friends. I have another friend, who I’ve never told about this, who tried setting me up once. He seemed like a good guy and we chatted. I didn’t overshare and kept it casual. But all he told my friend was that I was nice. He wasn’t interested in dating me. I’ve asked this same friend if she had any other single friends once. She said she had one guy she knew and then said she’d ask him. Weeks later I asked her about him and she said she was evasive. That told me he wasn’t interested. Most of my friends are married, or getting married, so double dates aren’t something they’re interested in.

OP posts:
ForPoliteRaven · 07/06/2025 15:05

MoominMai · 07/06/2025 15:02

@ForPoliteRaven have you tried any activity groups like walking/hiking or if you’re into history any local history societies. I understand you as I was in a similar boat not so long ago. I found someone from one of these groups and I too was v inexperienced. Tbf I had had 2 mini relationships but they didn’t involve sex. I’m single agin now and an introvert also but once I’m up to it this is probably what I’ll do. I feel you on the OLD aspect, it’s just awful in y experience like ruins your confidence more so so I vowed to never ever use it again and been over 15 years and I haven’t. All the best in your search ♥️

Edited

I love history. The local historical societies are filled with retirees, so there aren’t opportunities to meet single men. If I had the money, I’d move to another state lol.

OP posts:
ForPoliteRaven · 07/06/2025 15:09

CoffeeFroth · 07/06/2025 14:41

I'm not surprised that you have low self esteem considering the way you have been treated.
What about concentrating on improving your social circle and getting to know men without the pressure of dating.
Have you ever asked any of the men for feedback after your dates?

I’ve been ghosted and/or blocked on dating apps so there hasn’t been an opportunity to ask. One was the result of a blind date because my mother handed out my number to a random guy. I’m an oversharer, so that could’ve been the issue with the blind date. I’ve worked hard on changing that, so I don’t do it much anymore. I changed careers four years ago, so my social circle has expanded, but most of them are already paired off. I have one friend who isn’t interested in dating or marriage. She’s had her fill of men and is content with being single. And here I am the only one with no dating and sexual experience.

OP posts:
pimplebum · 07/06/2025 15:10

It all about expectations , I did on line dating to get out eat nice meal and meet people and romance was a possible side effect

I’ve known people go on 3 dates and give it up as a failure

I think there are underlying esteem issues ? Is there a support group for people with same condition?

sex parties are for uber confident sex experts not virgins with esteem issues
there are professionals who deal with sex problems sex surrogates?

MoominMai · 07/06/2025 15:11

ForPoliteRaven · 07/06/2025 15:05

I love history. The local historical societies are filled with retirees, so there aren’t opportunities to meet single men. If I had the money, I’d move to another state lol.

Do you know what? Even if the history groups are filled with elders, just join anyway if you enjoy history. Who knows, someone there might know of another suitable single. That’s what I’ll be doing. Even if I meet no one there it’s okay because I love history so at least my happiness was boosted! If I were you, just attend anything you think you will enjoy. They do say, sometimes it can happen when you least expect or aren’t even looking!

ForPoliteRaven · 07/06/2025 15:11

Rainytoday · 07/06/2025 14:26

You say you have had less than ten dates. That’s not very many. Keep going!

Also good idea re the dog.

Sometimes I consider myself lucky to even have those. Most of my messages go unanswered. My attempts to engage men in public are unsuccessful too.

OP posts:
ForPoliteRaven · 07/06/2025 15:13

MoominMai · 07/06/2025 15:11

Do you know what? Even if the history groups are filled with elders, just join anyway if you enjoy history. Who knows, someone there might know of another suitable single. That’s what I’ll be doing. Even if I meet no one there it’s okay because I love history so at least my happiness was boosted! If I were you, just attend anything you think you will enjoy. They do say, sometimes it can happen when you least expect or aren’t even looking!

I’ve heard that advice too. There are times when I’ve given up and stopped looking. But it still hasn’t happened even while I’m focusing on myself.

OP posts:
IfIDid · 07/06/2025 15:16

In your shoes, OP, I’d try to separate the issues out. I think improving your self-esteem is key to all of it. I have an old university friend with a very disfiguring facial birthmark on most of her face— the raised kind that can’t just be masked with cosmetics. From the first moment I met her, her copper-fastened confidence struck me. She had to develop it, because of the way people respond to her appearance — kids asking questions, people double-taking, some people being cruel. She dated and is married with children. Someone else I know, though more of a friend of a friend, has achondroplasia and is only about 3 ft 6 tall. Likewise has had to develop rock-solid self-esteem, because blending in isn’t a possibility. Currently single, but has had longterm relationships.

Doing OLD needs good self-esteem anyway, but doing so with a physical difference even more so. I would work on that first.

ForPoliteRaven · 07/06/2025 15:18

pimplebum · 07/06/2025 15:10

It all about expectations , I did on line dating to get out eat nice meal and meet people and romance was a possible side effect

I’ve known people go on 3 dates and give it up as a failure

I think there are underlying esteem issues ? Is there a support group for people with same condition?

sex parties are for uber confident sex experts not virgins with esteem issues
there are professionals who deal with sex problems sex surrogates?

Sex surrogates would be illegal in my state. I live in a really conservative state, so it would be considered prostitution. I joined an online support group for my condition but most of the people I’ve chatted with are already married. They tell me to stop actively looking for a relationship because it happens when you least expect it, or I get spammed with “cures” for my condition. There are only treatments and no cures. I agree that my self-esteem is low, or non-existent, because of the constant bullying and jabs about my appearance throughout my life.

OP posts:
Secretsquirels · 07/06/2025 15:18

I have a friend in a similar position. She’s not so stunningly attractive that she can get by on looks alone, but she’s definitely not unattractive either.

I suspect that for her it’s a bit of a vicious circle. She’s not flirty/playful/provocative because she hasn’t had a lot of experience. But then when she dates guys aren’t interested because she’s giving across professional/sisterly vibes.

Im wondering whether you are the same and some more fun/flirty behaviour might help.

I’m also wondering whether you are overweight? I know that’s a hard question but it does make a huge difference for dating.

If your friends can’t pinpoint what is causing it, then I would say try some approaches where you’re meeting people in the same sorts of vibes as your friends. Something like group solos holidays could be good because there is no dating focus but you’re with people for long enough to get to know them properly.

Finally, I’d ask you to consider whether you’re sure that you should be dating men rather than women? Sometimes people who haven’t realised yet give off a vibe that other people recognise on a subconscious level before they realise consciously.

ForPoliteRaven · 07/06/2025 15:19

IfIDid · 07/06/2025 15:16

In your shoes, OP, I’d try to separate the issues out. I think improving your self-esteem is key to all of it. I have an old university friend with a very disfiguring facial birthmark on most of her face— the raised kind that can’t just be masked with cosmetics. From the first moment I met her, her copper-fastened confidence struck me. She had to develop it, because of the way people respond to her appearance — kids asking questions, people double-taking, some people being cruel. She dated and is married with children. Someone else I know, though more of a friend of a friend, has achondroplasia and is only about 3 ft 6 tall. Likewise has had to develop rock-solid self-esteem, because blending in isn’t a possibility. Currently single, but has had longterm relationships.

Doing OLD needs good self-esteem anyway, but doing so with a physical difference even more so. I would work on that first.

How can I do that? Therapy isn’t in my budget right now even with insurance.

OP posts:
Velmy · 07/06/2025 15:24

Are you open about your skin condition on your dating profile OP?

I have a friend with limb difference, which wasn't obvious on dating apps (not on purpose, he just didn't mention it). He has a bunch of bad experiences where people turned up and were shocked/freaked out by it.

After a few of these he changed his photo so it was obvious, mentioned it in his bio etc. He had much more success that way and is now married to someone he met on an app!

TryForSpring · 07/06/2025 15:24

I would recommend these two books, OP. Available on Amazon.

Over 40, never had a boyfriend or any sexual experience
Over 40, never had a boyfriend or any sexual experience
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