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No dating experience at 30


Tinydance
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Hey it's Tiny! 36-year-old woman.  Live alone in an apartment owned by my parents and renting from them the past seven 7.5 years. Working as a disability and mental health support worker for eight years. Have a Bachelor of Psychology and two community college diplomas in mental health and disability.

I'm looking for marriage and to have kids. I've had a number of serious relationships but they were all only two years or just over two years. I lived with one partner and was engaged to him. Now have been single for 1.5 years or so.

This guy messaged me on a paid dating website which is meant to be for serious relationships. He's 30 years old and he works full-time for a big computer company where he assembles computers from scratch. Before that he worked as an IT technician support person in schools for eight years. He's renting a house by himself. He's a nerdy guy that's really into video games, Star Wars, Marvel movies, things like that.

We video called for two hours because a COVID lockdown started. He seemed nice in the video call and we continued messaging each other online. He was messaging me every day but he didn't bombard me or anything. Like, if I stopped replying that day he didn't message more either. Unfortunately we were confined to only talking online for two weeks due to lockdown.

When lockdown eased off we went out for dinner and saw a movie at the cinema. Afterwards we went for a drink and then just talked in the carpark for a long time because everything closed. He seemed nice but I found the conversation a little awkward but wasn't sure if he was just shy and nervous. I was actually nervous myself because it all got kind of built up by talking every day for two weeks and I was anxious that it might not go well in person.

He'd been telling me a fair bit about his family online and on the night as well. I just asked jokingly if he'd told his family that he was coming out with me. He said he did and that his Mum was happy and excited. I was like, oh why? And he actually admitted that he had never dated anyone before! He said he sort of had a thing with a girl he knew from school but she messed him around or something. I didn't know if he'd had sex before or anything because I didn't ask.

I asked him if he hadn't dated anyone because he was shy. He said yes due to that and also that he always worked full-time in male dominated environments and he wasn't into going out clubbing and partying. I mean, he didn't seem weird or looked bad or anything so I found all this very surprising.

Then we continued talking online and he had caught up with his Dad and his sister. And he said that his Dad said hi to me. Then he also said his sister said that when COVID restrictions ease further that we should go to her place for dinner. I said thank you for the invitation but I want to get to know him more first before I meet his family. He actually seemed embarrassed and kind of back tracked and was like: "Oh, my sister just meant in general in the future that we could come for dinner eventually. I think she was just trying to be nice."

It was definitely coming through though that he has no dating experience because of how full-on he was acting. Also I'm not sure what exactly he told his family about me. Like, did he say we are actually dating or are in a relationship? We met in person only once. 

I'd like to give him a chance but I'm worried that his lack of relationship experience could be a problem. I mean, I had my first relationship when I was 16 years old and now I'm 36. I've dated a lot and hooked up a lot and done all that stuff. Now I'm ready to really settle down and start a family. I'm just not sure if someone who's never been with anyone is a good candidate for that. 

For one thing if someone wanted to be with me or marry me, I'd want to be sure they actually want ME as a person. Not because they're 30 and I'm the first person they ever had. Don't get me wrong, I'm pretty, I'm nice and bubbly and smart. I'm a bit overweight but it hasn't really been a problem because I'm more so chubby, I'm not huge. So I know I'm likeable but I also feel a bit like there would be that niggling feeling that the person is only choosing me because they've never had anyone else.

Any thoughts on this? Do you think I should give him a chance? I like him and do want to know him more but I'm just worried...

 

 

Edited by Tinydance
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1 hour ago, Tinydance said:

Do you think I should give him a chance? I like him and do want to know him more but I'm just worried..

Go with it. You barely know him but so far you like him. See what happens.

Maybe he's a bit nerdy but one of those Clark Kent guys who are Superman in bed.🦸‍♂️

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My first thought is that you are creating the "I wouldn't want to be in a club that will have me as a member" dilemma. What makes you think he can't get dates other than you?

He sounds pretty decent as well as intuitive and sensible, even if late to the game. So I'd keep an open mind and get to know him and see how it goes. Just don't over invest, which goes for anyone you meet. Just take your time getting to know him and keep your options open. Pace yourself and see what's what.

 

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For me it would be a dealbreaker including because of his reasons why.  He didn't date because he didn't want to.  Didn't want to put in the effort.  And seems unconcerned.  When I was looking for marriage and family I wanted to be with someone who also wanted that enthusiastically and part of wanting that is putting in effort to date and form relationships.  Even if the person didn't date as a teenager then certainly as an adult.  And certainly by 30 years old.  The fact that he doesn't seem concerned either way and attributes it to external factors would be a reason I would not want to meet him.  As an aside I'm tired of the "nerd" label unless it's meant positively I guess - it's such a knee jerk reaction sometimes.  All a guy has to do is say he's into math and/or technology, is very intelligent and bingo he's a "nerd".  Especially if you're meeting people to date treat them as individuals. 

And no it's not inconsistent for me to also say if a man hasn't dated by age 30 he's likely not a good candidate for a serious relationship leading to marriage -because of this person's individual reasons. I can see reasons why it might be fine.  In this case, I'd pass particularly since you're very focused on getting married (as was I).

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3 hours ago, Tinydance said:

I've dated a lot and hooked up a lot and done all that stuff. Now I'm ready to really settle down and start a family. I'm just not sure if someone who's never been with anyone is a good candidate for that. 

Like you said, you two have only met up once.  I don't think either of you should be seeing each other as anything like 'my future', just yet, lol.

Not sure IF he's seeing you as just someone 'available & giving him attention', but you are right, sounds like he's lacking there 😕 .

Also, you know HIS interests.. are you into any of that at all?  he's a computer nerd.. ( much like my ex and boys, lol)... If he is like that, can you handle it?  Gaming is often!

 

IF you feel is just not for you.. is best to put an end to 'any expectations' soon.

 

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The only thing I would worry about is how he is with commitment. Seeing as how he’s never dated before or had a relationship. My concern will be if he’s really ready to settle down.  You will be his first everything. On the flip side you should see where it goes but go slow keeping that in mind. 
 

However, I did date a wonderful guy and he was in his thirties still a virgin and never dated anyone because he felt being overweight at the time hindered him. He was very engaging and direct with what he wanted and his intentions. Unfortunately it didn’t work out as there wasn’t much chemistry.   So this guy may be more settled then you think.

 

The only way to know is to date him. I say give him a chance! We all have to start somewhere and who knows he may have been waiting for someone perfect for him to come along! 

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Hey, Tinydance. It seems like there is initial interest and that things have been going well so far. You may be overthinking. When something is new like this, that's probably natural.

I think your initial concerns are valid, though, so let's ~explore

Re: Experience and Your Type. Personally, I do not think that inexperience in and of itself is a deal-breaker. As long as the person and I are otherwise compatible, emotionally mature, and open-minded, I am not likely to be deterred by inexperience. I understand, though, that it likely depends on the person. If your type is someone already experienced in romance or in the bedroom, and you know you would not be willing to help someone out (even if he was willing to adapt to you) in those departments, then that is worth acknowledging and accepting.

I will say - the inexperience at 30 may make a reasonable person wonder why the person has no experience - i.e., are any red flags the cause of that? If there are no red flags underneath that, and he is not filtered out because he is not your type (re: above), then all is well, no? 

Re: Awkward Moment Regarding Sister's Place. Less that inviting you for dinner at his sister's was maybe a bit awkward or forward at this point (chalk it up to inexperience on pacing?), no harm done. I think you rightly asserted a boundary and he seemed to be willing to go instead at the pace you wanted. I'd say you did a nice job communicating in this situation.

Re: First Date/Love. You said you want him to want you for you, and not just love you because you are his first. It happens all the time that someone marries and stays with their "first." If it works, it works. If you know you are lovable, and he seems to love you, then he probably does love you. This is getting a little ahead of ourselves, though. As a wise ENA poster once put it, "I want to get to know him more first." 🙂 Once you do, you'll have a better feel for if he is loves you in the emotionally mature way you seem to want. 

Hope this helps.

Edited by Pleasedonot5
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Sure give it a shot and you'll see if there are any more niggling feelings! :D (Sorry, that word just sounds funny so had to use it :p ). He's prob just shy and works a lot, so no red flags here....

no experience can be a good thing right? like no smoking, gambling, hmm lol

If I dated someone who never really dated anyone, I'd feel pretty special...wait, now i don't feel soo special 😞 :D

 

Edited by mical
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And if he had TOO MUCH dating experience one might get intimidated. 

1. It sounds like he is work oriented. I'm not sure why you're giving him a hard time or insinuating something is wrong with him because he's not dating. Ever think that's why he's on the dating sites? He's actively looking to date and I'm sure you're not the only woman he's chatted with online. Dating is hard when you're older. Just because none of his past experiences led to a relationship doesn't mean theres something wrong with him. 

2. He most likely DID NOT tell his family he was official with you, he probably told them he was "seeing" someone or hanging out with someone special. It's exciting when you first meet people, he probably wants to share that with his family. 

3. He is the marrying type. He doesn't have messy exs. He doesn't have children from abother relationship. Sounds like he's successful. Clearly, even during his bachelor years he clearly wasn't into hooking up with just anyone and anything. Idk, if i met a guy like that I would think he was made specifically for me. You could have a man that has loved only one woman: you

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On 6/14/2021 at 8:45 PM, Tinydance said:

Any thoughts on this? Do you think I should give him a chance? I like him and do want to know him more but I'm just worried...

 

One of my best friends never had a relationship until he was 31. Had sex but no luck finding girl for relationship even though he tried here and then. Then he met a girl. Just a bit younger, kinda similar experience(had a few relationships here and then). She didnt like him at first, even got drunk and got mad at him(because they have gone out in the same company of friends) but he slipped her his number and she apologized later. They started talking, started going out as friends and started dating later down the line. They figured it out quite nicely, got serious, he takes her to dinner dates, families met and got along, even started job together, started living with each other and engaged later. What I am trying to say is, it doesnt matter as long as you can figure it out and get along. He seems OK(steady job in IT, lives alone etc.), he likes you and wants to settle, so at least try. You would have to probably take initiative for few stuff at first though, even maybe teaching him few stuff. Especially if we are talking physically. 

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On 6/15/2021 at 6:12 AM, Wiseman2 said:

Go with it. You barely know him but so far you like him. See what happens.

Maybe he's a bit nerdy but one of those Clark Kent guys who are Superman in bed.🦸‍♂️

Ha ha ha Thanks Wiseman! Let's hope so 😉

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On 6/15/2021 at 6:33 AM, DancingFool said:

My first thought is that you are creating the "I wouldn't want to be in a club that will have me as a member" dilemma. What makes you think he can't get dates other than you?

He sounds pretty decent as well as intuitive and sensible, even if late to the game. So I'd keep an open mind and get to know him and see how it goes. Just don't over invest, which goes for anyone you meet. Just take your time getting to know him and keep your options open. Pace yourself and see what's what.

 

Thanks DancingFool! Well yeah I am actually doing that and just giving him a chance and getting to know him. So far we've met in person once but we're meeting again for a walk in the park and to have something to eat this weekend. We just message each other in an online chat a bit basically every day. I must admit he did say something weird again. I was telling him how much I don't like being an only child and that for that reason I can't be an Aunty and have nieces and nephews. His sister is pregnant and he said: "I'm sure my sister would love for you to be an Aunty". So I'm definitely keeping an eye on these kinds of comments. I said to him that maybe he shouldn't say those things because we don't know yet if we'll end up together. He said not to worry and that he's on the same page and just wants to get to know me more.

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On 6/15/2021 at 7:58 AM, Tonight.majestic said:

Are you afraid that you'll like him enough to enter into a relationship with the thought of marrying him?

But that him never having had a relationship, he might want to explore other options before settling down?

Because that's what I see it as.

Well, it's a combination of reasons actually why I'm a bit worried. I'm not sure if he would want to explore other options but I guess I would be more so worried that the inexperience can affect the relationship. 

I feel like because I'm in my mid 30's maybe I'm not that patient anymore with someone that has no experience. I had a couple of dating experiences with guys who are pretty inexperienced in relationships and sexually in the last 1.5 years. I tried with them but I think I lost my patience eventually. I mean, I didn't lose it straight away. One of them I dated like six weeks and the other one a few months. I suppose in the end I realised I wasn't really into them enough to have that level of patience. And those guys were even younger and I think I was worried about the age gap.

One guy I dated was 25 and I was 34. He was originally from India and only living in Australia about 3-4 years. He seemed to had led a very conservative life where he was from the only state in India where drinking alcohol is illegal. He never went to parties and I basically knew as time went on that he had never been with any girl ever. Then there was another guy who was 28 and I was 36. He was kinda awkward but had been with one girl for four years in his late teens and early 20's. I dated him for a few months but I guess I wasn't feeling it that much and when we finally had sex it was pretty awkward. I do realise though that there was a pretty significant age gap between these guys and myself too. So even if they had experience with women it may not have been likely they wanted kids and marriage and it was probably a bit of a dead end in that sense.

 

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On 6/15/2021 at 8:06 AM, shellyf62 said:

He sounds lovely, not a player wanting to hit & quit.

Give him a chance, you might be pleasantly surprised.

Thank you. Well I am giving him a chance so far but I'm keeping my eyes and ears open, you know lol

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On 6/15/2021 at 8:43 AM, Batya33 said:

For me it would be a dealbreaker including because of his reasons why.  He didn't date because he didn't want to.  Didn't want to put in the effort.  And seems unconcerned.  When I was looking for marriage and family I wanted to be with someone who also wanted that enthusiastically and part of wanting that is putting in effort to date and form relationships.  Even if the person didn't date as a teenager then certainly as an adult.  And certainly by 30 years old.  The fact that he doesn't seem concerned either way and attributes it to external factors would be a reason I would not want to meet him.  As an aside I'm tired of the "nerd" label unless it's meant positively I guess - it's such a knee jerk reaction sometimes.  All a guy has to do is say he's into math and/or technology, is very intelligent and bingo he's a "nerd".  Especially if you're meeting people to date treat them as individuals. 

And no it's not inconsistent for me to also say if a man hasn't dated by age 30 he's likely not a good candidate for a serious relationship leading to marriage -because of this person's individual reasons. I can see reasons why it might be fine.  In this case, I'd pass particularly since you're very focused on getting married (as was I).

Well actually I agree with what you wrote. I also realise my life has been shaped by firstly being a woman, secondly a cute woman (not trying to be up myself) and thirdly having a very outgoing, chatty and bubbly personality. I've usually actually had the confidence to even ask out guys (and some women) myself. I had my first boyfriend at sixteen and I asked him out. He was my friend and he said he wanted to ask me but he was too shy. When I was 18 I asked out another guy and I dated him for nearly two years. To be really honest I asked out most of my partners myself because I wasn't scared to do it. 

I know this may come across as judgemental but when I came across guys who were in their mid to later 20's or 30's and they haven't been with basically any women, I did find that off putting. And maybe in the past more so had that gender biased mindset of "Well you're a man so why are you wimping out and not going after women?" 

When I was twenty five I met this Indian man on online dating who was twenty seven. On the outset he was actually a good catch. He was cute and had a Master's Degree in engineering and worked as an engineer. He was nice and sweet but it was coming across that he was very inexperienced. We went on about five long dates and he'd never kissed me or did anything at all. I thought, what is going on here. But he kept contacting me and asking out on a date so I thought the problem must be shyness. So on our fifth or sixth date I was seeing him off at the train station and as his train pulled up I kissed him. 

He lived with some room mates and I'm not sure if maybe they were egging him on to make a move. He was house sitting someone else's place and he asked if I wanted to come over there. Apparently his friend was fine with it. I basically was getting the jist he wanted to fool around or hook up or whatever but I thought it was OK because we'd been on six dates. 

Anyway I came over and I guess he was really nervous and I was a bit as well. We were drinking alcohol and I think we forgot to get any soft drink and we were just drinking straight bourbon or something. So it was very strong and we were kind of overfilling it. When we were both drunk I guess I was being really forward and I asked him if he'd been with many women. He said that he had slept with only one woman once in his life ever and it was a prostitute.

Anyway the whole thing was an absolute disaster! We had too much to drink and I don't think we even really did anything. I passed out and I'd taken off some of my clothes. But I didn't take off my underwear so that's why I had a feeling we didn't even have sex. I woke up to him having vomited (he admitted it) all over all my clothes which were on the floor! It was his male friend's place and I had nothing else to change into and it was winter. So I didn't wash the clothes because it was so cold and I didn't want to wear wet clothes. So I put all the vomit clothes and I went home!

Keep in mind this was like 11-12 years ago and I had a different mindset and I thought it was really bad to sleep with prostitutes. I was extremely put off by what that guy told me and also very put off that he made no effort to be with women and just went straight for a prostitute. I was also very put off by the vomit incident but as you can imagine I was dressed entirely in clothes covered in vomit! 

The guy apologised profusely and begged me to change my mind. He said he was really sorry he'd slept with a prostitute and he only did it because he was so shy and nervous with women and he'd never been with any women by the age of 25. He said his friends were making fun of him for it so he wanted to just get it over with and went to a prostitute.

Anyway after that I actually felt guilty about ending it because I thought I was too harsh on him and he was actually a lovely guy. I wanted to at least contact him and apologise but I'd changed phones and I lost his number.

As the years went on I began to not really think about gender roles and in fact be against gender roles or stereotypes. I began to see that it's probably hard as a guy if you're actually shy and you don't have that alpha male or Casanova/player thing going on. Not that many women hit on guys or ask out guys themselves and they just wait for guys to come to them. That's actually also Howard women have been brought up or conditioned by society. I always got told I need to wait for guys to come to me first and to play hard to get and not seem "desperate". But I thought, OK I won't act desperate but if I like a guy I'm just going to let him know.

I have shy male friends and one of them is really attractive but he's quiet. He's been with women but not that many and not as many as you think he should have because he's really hot and he has a good job. 

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On 6/15/2021 at 8:45 AM, SooSad33 said:

Like you said, you two have only met up once.  I don't think either of you should be seeing each other as anything like 'my future', just yet, lol.

Not sure IF he's seeing you as just someone 'available & giving him attention', but you are right, sounds like he's lacking there 😕 .

Also, you know HIS interests.. are you into any of that at all?  he's a computer nerd.. ( much like my ex and boys, lol)... If he is like that, can you handle it?  Gaming is often!

 

IF you feel is just not for you.. is best to put an end to 'any expectations' soon.

 

No I don't feel that he's not for me. I actually love more nerdy guys. I live in Australia and not that it's bad in and of itself but there are many of these "Aussie bloke" kind of guys. Like, guys who are tradies (labour work) and love to go to the pub and "have beers with their mates", watch footy (Australian football), cricket, eat meat pies and sausage rolls. I know it sounds like I'm hugely stereotyping but there are actually a lot of guys I meet or have met who are within that stereotype. 

I was with a guy for two years who was the manly Aussie bloke type and in the end I think I really began to think that we don't actually have anything in common. I'm not that good with computers but just personally I would prefer to date a guy who has a more intellectual job and more intelligent interests. I'm not saying people who do trade work are dumb but what I mean is I really don't relate to a lot of those types of guys. I hate sport, I hate the gym. My ex from way back was a very alpha manly kind of guy who loved sport, camping, had a ute car, eating sausage rolls. Like for real lol

Regarding video games, it's true I am not a gamer myself. But I like some video games and I'm happy to play them. I have and do play video games with my friends sometimes. But I don't have any gaming consoles myself so I guess yes you can say video games are not an actual hobby for me. 

My ex fiance had an astrophysics degree but he actually worked as a software developer with a successful software company. He was really into video games, You Tube and coding. I wasn't really into it myself but I watched You Tube with him and played some video games and always asked him about his work. I asked him what phone apps he was working on. Granted I kinda felt like he was speaking a foreign language when he explained it but I loved him and his interests were important to me because he was important to me.

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On 6/15/2021 at 9:00 AM, limichelle said:

The only thing I would worry about is how he is with commitment. Seeing as how he’s never dated before or had a relationship. My concern will be if he’s really ready to settle down.  You will be his first everything. On the flip side you should see where it goes but go slow keeping that in mind. 
 

However, I did date a wonderful guy and he was in his thirties still a virgin and never dated anyone because he felt being overweight at the time hindered him. He was very engaging and direct with what he wanted and his intentions. Unfortunately it didn’t work out as there wasn’t much chemistry.   So this guy may be more settled then you think.

 

The only way to know is to date him. I say give him a chance! We all have to start somewhere and who knows he may have been waiting for someone perfect for him to come along! 

Yes my concern also is mainly that this guy may not want to settle down and have a family or at least not in the time frame I need it to be. I'm 36 so biologically I really need to have kids maybe in the next year or two tops. Also I haven't actually asked him yet whether he wants those things because I didn't want to scare him off. I know he's excited to be an Uncle because his sister is expecting a baby. He loves dogs and I also love dogs but I guess that's not necessarily correlation that he wants kids lol

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On 6/15/2021 at 9:17 AM, Pleasedonot5 said:

Hey, Tinydance. It seems like there is initial interest and that things have been going well so far. You may be overthinking. When something is new like this, that's probably natural.

I think your initial concerns are valid, though, so let's ~explore

Re: Experience and Your Type. Personally, I do not think that inexperience in and of itself is a deal-breaker. As long as the person and I are otherwise compatible, emotionally mature, and open-minded, I am not likely to be deterred by inexperience. I understand, though, that it likely depends on the person. If your type is someone already experienced in romance or in the bedroom, and you know you would not be willing to help someone out (even if he was willing to adapt to you) in those departments, then that is worth acknowledging and accepting.

I will say - the inexperience at 30 may make a reasonable person wonder why the person has no experience - i.e., are any red flags the cause of that? If there are no red flags underneath that, and he is not filtered out because he is not your type (re: above), then all is well, no? 

Re: Awkward Moment Regarding Sister's Place. Less that inviting you for dinner at his sister's was maybe a bit awkward or forward at this point (chalk it up to inexperience on pacing?), no harm done. I think you rightly asserted a boundary and he seemed to be willing to go instead at the pace you wanted. I'd say you did a nice job communicating in this situation.

Re: First Date/Love. You said you want him to want you for you, and not just love you because you are his first. It happens all the time that someone marries and stays with their "first." If it works, it works. If you know you are lovable, and he seems to love you, then he probably does love you. This is getting a little ahead of ourselves, though. As a wise ENA poster once put it, "I want to get to know him more first." 🙂 Once you do, you'll have a better feel for if he is loves you in the emotionally mature way you seem to want. 

Hope this helps.

Thank you, really good response and some great points there. As far as red flags go, well at this point I didn't really see any yet. I'm definitely keeping my eyes and ears peeled open lol 

I think you're right in the sense that if I'm looking for a long term relationship, I above all want it to be a compatible person who I actually love. Just because someone may be let's say older than I and have lots of experience doesn't automatically make them right for ME. Honestly number one thing for me is what people call that spark and connection with someone. Feeling comfortable with them, being able to be totally myself and have a laugh and you know, "marry your best friend" as they say. If I find that in someone with no experience I realise it would be a mistake to reject them just based on that.

 

 

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On 6/16/2021 at 9:37 AM, mical said:

Sure give it a shot and you'll see if there are any more niggling feelings! :D (Sorry, that word just sounds funny so had to use it :p ). He's prob just shy and works a lot, so no red flags here....

no experience can be a good thing right? like no smoking, gambling, hmm lol

If I dated someone who never really dated anyone, I'd feel pretty special...wait, now i don't feel soo special 😞 :D

 

He he Well yeah I guess you can feel special if you're someone's basically first everything but for me there is also that fear that maybe I'm not actually special but I'm just the first person that wanted to be with THEM. 

I'm not going to straight away reject someone based on no experience but I guess it would also depend on how their inexperience affected the relationship. Like, how they behaved and what their expectations were. I can't help feeling that someone who is 30 and never dated anyone is kind of stuck in a more teenager dating stage of life. Like, maybe they're really going to ranticize their first ever relationship. But I could be wrong...

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On 6/16/2021 at 11:21 AM, rchubn said:

And if he had TOO MUCH dating experience one might get intimidated. 

1. It sounds like he is work oriented. I'm not sure why you're giving him a hard time or insinuating something is wrong with him because he's not dating. Ever think that's why he's on the dating sites? He's actively looking to date and I'm sure you're not the only woman he's chatted with online. Dating is hard when you're older. Just because none of his past experiences led to a relationship doesn't mean theres something wrong with him. 

2. He most likely DID NOT tell his family he was official with you, he probably told them he was "seeing" someone or hanging out with someone special. It's exciting when you first meet people, he probably wants to share that with his family. 

3. He is the marrying type. He doesn't have messy exs. He doesn't have children from abother relationship. Sounds like he's successful. Clearly, even during his bachelor years he clearly wasn't into hooking up with just anyone and anything. Idk, if i met a guy like that I would think he was made specifically for me. You could have a man that has loved only one woman: you

Well yes when presented like that it does sound appealing lol I think maybe I'm a little jaded because I've been dating and in relationships for twenty years and I've had plenty of bad experiences so I feel like I don't have much capacity to have those rose coloured glasses on, so to speak lol 

I definitely want a serious relationship and have been in some and even engaged. But sexually I've been a real wild child. I won't go into the details. Nothing illegal don't worry lol I guess I also just worry that may come as a shock to someone who has never been with anyone. But that of course doesn't mean that someone inexperienced is only looking for other people who are the same. Maybe it's not a problem. I also don't need to mention anything about my sex life unless he specifically asks.

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On 6/17/2021 at 3:05 AM, Kwothe28 said:

One of my best friends never had a relationship until he was 31. Had sex but no luck finding girl for relationship even though he tried here and then. Then he met a girl. Just a bit younger, kinda similar experience(had a few relationships here and then). She didnt like him at first, even got drunk and got mad at him(because they have gone out in the same company of friends) but he slipped her his number and she apologized later. They started talking, started going out as friends and started dating later down the line. They figured it out quite nicely, got serious, he takes her to dinner dates, families met and got along, even started job together, started living with each other and engaged later. What I am trying to say is, it doesnt matter as long as you can figure it out and get along. He seems OK(steady job in IT, lives alone etc.), he likes you and wants to settle, so at least try. You would have to probably take initiative for few stuff at first though, even maybe teaching him few stuff. Especially if we are talking physically. 

You are right, if there is a good connection and attraction it doesn't really matter. I guess I still want to give him a chance for sure but I must admit I do get a little "blah" about being with some who has no sexual experience or hardly any. I had sex when I was 18 and I've done a lot of stuff since lol So to me it's sort of like second nature, if that makes sense. I find it hard if the person is awkward sexually or doesn't know what they're doing because it kind of kills the mood. But I think I also need to think back to my first couple of sexual experiences and they were 100% scary and awkward lol Actually pretty amusing to be honest lol

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11 hours ago, Tinydance said:

 I was telling him how much I don't like being an only child and that for that reason I can't be an Aunty and have nieces and nephews. His sister is pregnant and he said: "I'm sure my sister would love for you to be an Aunty". 

.....Pot meet kettle.....

Tiny, what you said was just weird af and he responded only way he could - trying to be nice and encouraging with you that you would be a good aunty.

It seems that you are very fixated on what might be wrong with him while paying zero attention to what you are saying yourself. You might want to give your own issues some thought - it's the only thing you control. Are you actually trying to push him away already on some subconscious  level?

I mean, if you feel so uncomfortable, then just let him go now and be done. 

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12 hours ago, Tinydance said:

Thanks DancingFool! Well yeah I am actually doing that and just giving him a chance and getting to know him. So far we've met in person once but we're meeting again for a walk in the park and to have something to eat this weekend. We just message each other in an online chat a bit basically every day. I must admit he did say something weird again. I was telling him how much I don't like being an only child and that for that reason I can't be an Aunty and have nieces and nephews. His sister is pregnant and he said: "I'm sure my sister would love for you to be an Aunty". So I'm definitely keeping an eye on these kinds of comments. I said to him that maybe he shouldn't say those things because we don't know yet if we'll end up together. He said not to worry and that he's on the same page and just wants to get to know me more.

I wouldn't like that either.  I dated someone with very little dating experience around that age. - we were in our late 20s His parents owned a wedding store- not just gowns -everything for weddings.  He took me there to meet them on the second date -he was renting a tux and made all sorts of pointed comments about our wedding plans etc.  Then he made more comments.  Then he asked if his sister who I'd met briefly once could stay at my apartment in the city because she had a date that night and that way wouldn't have to drive back to the suburbs.  Just oversharing/overstepplng/lack of appropriate social/dating skills.  I was done after about three dates.  We originally met on an online dating site.

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