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Dating an Inexperienced Guy


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Posted

He's 29. On our second date, he told me he hasn't been in a relationship for years. So, I imagine this means he hasn't been in a relationship since he was in college -- or even high school. He's an attractive guy, but I understand that he has probably had difficulties dating because he's 5'6''. He's an intellectual guy and has said it was rough dating in the Navy because he was just mostly surrounded by guy friends.

 

So, my question is this. I like this guy. And it's clear he likes me. We have our 3rd date tomorrow and next week we have plans to see a film screening and grab a bite after work.

 

On our last date, he said it's awesome to meet someone that he clicks with and has common interests with. Overall, he said he's never dated anyone with a similar intellectual curiosity.

 

So all of this is pretty great! On the other hand, I think because he has a lack of experience with women and dating in general, a part of him seems very shy.

 

I like the pace of things so far. But how do I deal with making sure he knows I'm physically attracted to him? So far, we have only hugged hello/goodbye. I want him to feel comfortable and for it to be natural. Do I wait for him to go in for a kiss or a warmer hug? Should I just go for it?

 

I don't want him to think that I simply view him in a platonic way. But I also don't want to rush anything. I'm going to assume that it has been some time (possibly years) since he has even slept with anyone.

 

Any thoughts or suggestions would be super appreciated.

Posted

It's called flirting..........................

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Posted
It's called flirting..........................

I've flirted with guys who are confident. This is the first time I've ever been interested in someone who is shy and has admitted to not being in a relationship for years, though.

 

So, I should just be flirtatious? Maybe I'm overthinking it. :rolleyes:

Posted

I would not assume he hasnt had sex simply because hes shy or hasnt been dating.

 

What about some sexy flirty texts to test the water?

Posted

 

So, I should just be flirtatious?

Yes!!! Guys, confident or shy look for "signals". Plus it's so much fun to build up that sexual tension.

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Posted

Just get handsy and make whatever needs to happen happen yourself, at your pace. He'll pick it up after a bit. :) But no, don't wait around for him to get the courage to make moves - it's actually a bit hurtful to him to expect him to take that role initially bc he's got no pedigree to rely on to tell him how and he'll just be clumsy and eff it up and feel dumb and lame. But you know, so you do it.

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Posted
So, I should just be flirtatious? Maybe I'm overthinking it. :rolleyes:

 

Maybe. ;)

 

My ex BF was also very inexperienced (as in, no prior GFs), but trust me, the response is the same. He didn't run away and hide when I flirted with him. If anything, seeing that I was interested/flirty gave him the freedom to relax a little and be a bit more confident with the move-making. I mean, we had sex on date three, and I'd imagine that if it's been a while since your guy has slept with anyone, he's probably raring to go, even if he's not showing it.

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Posted

I like shy men. You can give them clues to your attraction and they won't jump on you as if it's an invitation to have sex right there on Starbuck's table.

 

Use touching. When you speak to him just gently touch his arm for a moment, smile a lot, when you stand in line just stand close to him and touch him. Have a body language that says you 2 are together.

 

Don't worry about his relationship inexperience. If he knows to be in a relationship with family, friends and co-workers (respect, consideration, time,) then he has the basic qualities to be in a romantic relationship.

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Posted

I know plenty of 5'6" guys who dated just fine and were confident, but it sounds like this one may not be confident, possibly, in the sexual arena. Maybe he's small (you know) and afraid to progress to you finding that out; maybe he feels afraid of a woman who has more experience because he's inexperienced; or worst of all, maybe he is just fearful in general, which causes a lot of problems and probably won't change.

 

If he doesn't kiss you soon, it may be the latter. I think you should start fishing and trying to find out if this is a lifelong problem of being fearful and stuck in place, and maybe ask him how he met his last gf and ask him how soon the relationship took off and make sure he even had sex with her. Time to start questioning him. Maybe it will make him start talking and you can find out what's up with him.

 

Now, I'm not saying this isn't a cheap trick, but when there were guys I wanted to kiss (even gay ones!) I would use my birthday as an excuse and demand birthday kisses. Hard to wriggle out of that one.

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Posted

Thanks all! All of this is super helpful. I'm going to be more flirty now that we will be on Date 3 tomorrow afternoon.

 

but it sounds like this one may not be confident, possibly, in the sexual arena. Maybe he's small (you know) and afraid to progress to you finding that out.

I'm afraid that this might be the case and this came to my mind after our second date. He has been so gentlemanly and polite and I seriously appreciate that. I can tell he is really into me and getting to know me more and spending more time together. It's sweet!

 

I have two male friends kind of like him - super shy and both had been single for years -- both of them have wives now! They suggested I do the same thing as above - make the first flirty move. They told me odds are it'll be received very, very well - even if he is on the shy side.

 

But I'm also worried that he might be (small) too. That did cross my mind. It doesn't make me hesitate necessarily - I've never been with anyone (small). But I can understand why he's really been sweet and is really interested in spending time together doing activities. We're getting to know each other, personality-wise and hobby-wise.

 

He has mentioned that he really enjoys working out and the results - he says last year he was 20 lbs heavier and losing that weight and working out has given him a confidence boost.

Posted

Follow the flow, it seems you hit on well, his 'inexperience' will fade over time, because the dude has probably still a social circles like friends or acquantainces. If he was a socially isolated recluse, then maybe you should be worried... he doesn't seem so. Even a timid, socially awkward guy can learn pretty fast how to be a good boyfriend. Don't overthink, I'm sure this story can work.

Posted

But I'm also worried that he might be (small) too. That did cross my mind. It doesn't make me hesitate necessarily - I've never been with anyone (small).

 

The height is not related to his size. Look at his hands, that's where you can get a preview :D

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Posted
The height is not related to his size. Look at his hands, that's where you can get a preview :D

 

Ah! For real? Many women assume that tall guys have bigger doings.. which is wrong. I didn't know about the hands thing.. why would that be?

Posted
Ah! For real? Many women assume that tall guys have bigger doings.. which is wrong. I didn't know about the hands thing.. why would that be?

 

Height can be deceiving.

 

I am not sure why the hands (and feet) are representative but in my long experience I have notice it's something quite accurate.

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Posted
The height is not related to his size. Look at his hands, that's where you can get a preview :D

 

Sorry but that is also totally unrelated!

 

Ain't no way you can tell.

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Posted
Height can be deceiving.

 

I am not sure why the hands (and feet) are representative but in my long experience I have notice it's something quite accurate.

 

Maybe the dude in question is a two-hander ;)

 

(Had to make a bad pun today)

  • Like 4
Posted
Sorry but that is also totally unrelated!

 

Ain't no way you can tell.

 

Bing hands and small penis, that's a curse :confused:

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Posted
Bing hands and small penis, that's a curse :confused:

 

Lol!

Yeah it was for him - very confident outside the bedroom but not so when in it.

He is mega loved up - happy in a long term RS now - we're still friends.

 

In this world we have showers and growers.

I like you though like someone not so experienced - or who like me takes a new man as a blank canvas - means I have to learn - means he does too.

 

It depends if an inexperienced man is up for learning. If they're not then all bets are off.

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Posted
But I'm also worried that he might be (small) too. That did cross my mind. It doesn't make me hesitate necessarily - I've never been with anyone (small). But I can understand why he's really been sweet and is really interested in spending time together doing activities. We're getting to know each other, personality-wise and hobby-wise.

 

I guess anything's possible but I'd suspect it's that he's closer to virgin than he's letting on.

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Posted

FWIW I haven't found much of a correlation with dating experience and the emotional maturity and communication skills it takes to make a relationship work. I've seen guys who were married multiple times that act like 5 year olds. I've seen guy just out of college be matrure.

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Posted

Being small doesn't matter nearly as much IF they are confident and have mastered the use of their hands and also know anything about geometry. But that's what worries me here. Because a dude who's hesitant isn't going to have that stuff mastered and is likely to be both small and basic in bed. But seriously, size doesn't matter that much unless the only thing you use is your penis.

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Posted
size doesn't matter that much unless the only thing you use is your penis.

 

The worst is when all they do is use their penis because they are happy with their size.

 

Makes for totally awful sexual encounters.

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Posted

I actually prefer low-experienced guys to people that think they know what they are doing based on " all the experience and know-how" they've accumulated. It's a really crappy attitude that I don't like.

 

Reasons include:

 

*I have found they may be shy, but they are way more respectful

 

*You may not know where you stand with them for a while, but that just means the relationship will go slower, enough time for you to really get to know the person.

 

*When you finally do have sex, it will be more meaningful for the pair of you. He maybe clumpsy but he will be more loyal ( not to be confused with clingy) to you in the morning and not want to gap it necessarly. The sex between you two will be more special as he gets sexual opportunties few and far between.

 

I bet every step for him getting to know you is an amazing experience and he is more grateful and appreciative for it.

 

He may be slow to show his emotions as he may be anxious and over-thinking things- possibly even more than you, it's possible that he hasn't really been this vulrenable in a while with anyone.

 

I think you may have to take the lead ( the more experienced one usually does) but then once he gets the hang of it, I'm sure he'll become comfortable enough to take the reins. It will just take him and you a bit longer to get there, and there is something really beautiful about that I think, something very special.

 

I think this seems very promising!

  • Like 5
Posted

Other comments aside that got off topic ...

 

The world is a strange place, to be sure. You simply do not know what is going on in other people's lives, or what is inside of people's heads. I've known a few people (men and women) who were virgins almost until age 30, I've known people who started having sex at age 12. Few and far between, you may say? I don't know. I've met people (men and women) who were very promiscuous and have done just about everything imaginable, I've known people who have never given/received oral sex from someone they've been with for many years. And a few who have not done IT in a long time because they have not dated in many years but have in the past. And one who was with a woman for five and a half years, living together for four of them, were engaged to be married, and he never had sex with her. I asked why, he never told me.

 

As for your situation with this guy, I would not sweat it. It doesn't sound like he's that extreme, he just hasn't dated in a long time.

  • Like 1
Posted
I actually prefer low-experienced guys to people that think they know what they are doing based on " all the experience and know-how" they've accumulated. It's a really crappy attitude that I don't like.

 

Reasons include:

 

*I have found they may be shy, but they are way more respectful

 

*You may not know where you stand with them for a while, but that just means the relationship will go slower, enough time for you to really get to know the person.

 

*When you finally do have sex, it will be more meaningful for the pair of you. He maybe clumpsy but he will be more loyal ( not to be confused with clingy) to you in the morning and not want to gap it necessarly. The sex between you two will be more special as he gets sexual opportunties few and far between.

 

I bet every step for him getting to know you is an amazing experience and he is more grateful and appreciative for it.

 

He may be slow to show his emotions as he may be anxious and over-thinking things- possibly even more than you, it's possible that he hasn't really been this vulrenable in a while with anyone.

 

I think you may have to take the lead ( the more experienced one usually does) but then once he gets the hang of it, I'm sure he'll become comfortable enough to take the reins. It will just take him and you a bit longer to get there, and there is something really beautiful about that I think, something very special.

 

I think this seems very promising!

 

Ha ha, yep that was me, once I'd got my feet wet I was off like an everlasting clockwork bunny. And, as you say, once I'd got the hang of things I was leading and showing her new things (I'd done an awful lot of reading, just had no one to love to try it on.) My wife, even now many years later thinks my initial inexperience is something special of our own.

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