Being a 'late starter' in life/inexperienced

[ILostMy20s]

Hello MN. Firstly, full disclosure: I'm a male, but I'm posting as I'd like to (hopefully) receive some friendly female advice. Please be kind, as this is something that is fairly sensitive...

So, I'm in a bit of a predicament. I recently turned 30, but it's fair to say I'm much more inexperienced in love than pretty much anyone else this age.

At school, I was always very shy around the opposite sex. Literally, I was the sort of guy to turn down girls who asked me for hugs! I'm not joking, I'd sometimes cross the road to avoid talking to some girls.

This kind of continued when I started uni. Still very shy/socially awkward, and I really felt like I didn't fit in. I suppose it didn't help that I lived at home and commuted, so I was socially isolated through that as well. But uni really wasn't a good time for me. Because of how I felt, I developed anxiety and struggled with my eating for a while. So I never experienced the typical 'student lifestyle'.

It took me a while after graduating to get better, but unfortunately only a couple of years later, I went through a very traumatic family event. To avoid the full details, essentially I ended up becoming a part-time carer for my mum unexpectedly. Because of this, for quite a few years, dating/relationships were really the last thing on my mind.

Anyway, eventually I got through that, and a couple of years ago, I got to know a friend of a friend very well, and I developed strong feelings for her. Unfortunately it wasn't mutual; she made it clear that she only considered me a friend. I was devastated, as I really felt to begin with that there was the possibility for more. But in a way I was relieved, because I was aware that she had much more life experience than me. She'd had a couple of long-term relationships (including living with a previous partner), as well as a few flings. I never admitted my inexperience to her, but she knew I'd never had a relationship before, and it made me realise that if she had been interested in me, I might have been quite 'disappointing' to her compared to other people she'd been with.

I've spent time working on myself since then, and have recently started OLD. Things have been going fairly well - I've had quite a few matches, and several good conversations. I feel comfortable chatting to people - I'm not totally socially inept! But, obviously, my concern is that if things continue to progress, things might become more difficult.

To be clear: I've never so much as even had a kiss, and yes, clearly I'm still a virgin too...

I know some people will probably read this and laugh, and wonder how it's possible, whether I've been living under a rock all this time or whatever. But I hope the context makes sense. As per my name, I feel like my 20s were a lost decade in my life compared to most other people.

I'm acutely aware that for many women, this is probably a huge turn off. At this age in life, you want a "man" and don't want to have to teach somebody everything...so in some ways, I guess it's better to not admit anything?

But equally I'm scared it'll then become an issue. And obviously, the longer I go without experiencing these sorts of things, the more left behind in life I become. It's not something I can really talk to anyone about, because there's quite a bit of stigma associated with it. I keep it to myself. My friends know I've never been in a relationship, but they don't know the full extent of it.

So, from a female's perspective, what would you say is my best course of action? Be upfront and honest with dates about my inexperience (at the appropriate time, obviously!), and hope it doesn't scare everyone off, or keep it to myself and just hope that things come to me naturally when they happen?

Thanks to anyone who has got this far.

Yes, I certainly don't envy what women have to put up with, when reading about a lot of people's experiences on here. And I know that I'm very fortunate in that I don't have to worry about the same sort of thing - my personal safety, being sent unsolicited photos, etc. Or at least, it's significantly less likely.

So I'll fully take onboard what you've said. It does surprise me that so many people fail at the basics - being a decent person shouldn't be difficult, should it?

That's a very good point, and great advice. Obviously when you're inexperienced, you feel like you do need to search online to find out how 'things are done' so to speak, but I am mindful that a lot of it is designed more for a male audience, and as such might not always be 100% the best advice possible.

I fully intend that whenever my time does come to be thoughtful and respectful of my partner's needs, not just my own.

You sound lovely, which is ultimately the most important thing. Sex is a work in progress, it can be improved whereas it’s much more difficult to improve a personality. Echoing others that I wouldn’t launch straight into it, just broach it when the timing feels right. I can imagine it could be a nice experience for a woman, actually, getting to share that with someone.

And for what it’s worth I’ve been with some rubbish lovers who’ve had plenty of experience. The best sex comes from being respectful, in tune with your partner and being attentive to their body, which it sounds like you won’t struggle with.

Bear in mind that when you make a move on someone you really fancy, you can still show signs of being nervous however experienced you are. Most people aren't smooth - there will be a stutter, a catch in the throat, unsteady hands, nervous giggles, moments when you're not in control, it's all normal. So if you stumble a bit in the throes of passion, she won't automatically think it's because you must be inexperienced, and therefore you don't need to be worried that she'll somehow guess and lose all attraction for you (not that she would even if she were fully aware that it was your first time!).

Also, this is just a hurdle you have to get over. So it's five potentially awkward minutes of uncertainty in exchange for a loving & fulfilling relationship - not a bad deal. Plus bear in mind that even if someone has had more relationship experience than you, they will have been winging it the whole time, and they will be winging it with you. You can't generally extract reliable blueprints from past experiences because life and people will always surprise you. It's not like they are halfway up the hill, waiting for you to catch up - because you will both be new to each other, you'll be climbing the hill together at the same pace.

As long as you're good company (cheerful, open minded, fair, generous, silly, playful, independent) and you have a good heart, you're golden. And you sound very nice & intelligent. I bet that once you meet someone, she'll be wondering how she got so lucky and how it's possible you haven't been snapped up yet. Good luck OP, I've no doubt you'll find someone lovely.

Practice with the OLD. You may not meet a long term relationship but can rack up dating experience and kissing experience and maybe even more. Then you won't be inexperienced anymore. I wouldn't mention the fact you're not experienced. Just ask lots of questions. What do they like, how do they like it? Every new relationship is pretty much starting from scratch to an extent because you are learning all about a new person who will like different things. Good luck.

I think you need to go on a few dates with a selection of women (on a dating site) on a very casual basis. with no real intention of getting involved so no need to worry too much about what they think if you are a bit awkward you don't need to see them ever again! If appropriate have a goodnight kiss, get some experience of being with a 'girl friend' putting your arm round her, holding hands, so that when you meet someone you really like you can cope with the basics without getting flustered, but can truthfully say you haven't had a serious relationship, when things get to that stage. Of course while practising you may meet the one...

Edit: Crossed with post above, similar idea.