To be concerned about his insecurities?

[Funwith]

I just started dating a guy I really like. I haven’t dated for years.

He’s so awesome and we get on so great. We joke around a lot.

However, within all of our joking around, he’s said a few things that I suspect are stemming from insecurities.

Like he jokes a LOT about how I should find someone more suitable. Every time I go out he jokes about whether I’ve met a better option yet.

He also sometimes ask questions that seem like he’d fishing for compliments, or maybe insecure about his looks “why do you keep saying I’m good looking?” “It’s so weird that you think I’m good looking”.

The strangest one, and the thing that prompted me to write this post, is that he makes a LOT of comments about how he’s not clingy and hates clingy women, but seems to want to spend time an inordinate amount of time together (which I have no complaints about, incidentally. I love spending time with him).

The thing is, he should be brimming with confidence. He’s an absolute catch. First time in years that I’ve met a man I’ve felt lucky to be dating.

None of this too that dramatic or impacting our day to day “almost-relationship” but I’m still getting to know him and I am worried these things are a sign of something deeper.

He is a perfectly lovely, normal man and possibly I’m just looking for problems, but it worries me a bit.

It’s so weird that you think I’m good looking”.

I really wouldn’t like this.

I only see two potential problems..
Either he is genuinely insecure and will need constant reassurance which is extremely tiring or... he is paving the ground for normalising controlling behaviour further down the line.

He's either very insecure or is doing the things he's accusing you of. Either way be careful.

Maybe previous girlfriends have said he's clingy? Sometimes when people make pronouncements about their personality eg. "I'm laid back." "I hate drama". The opposite is true but they're trying to persuade you otherwise.
He might be ok, just initially insecure or he might not.

How long have you been seeing him?

I’d echo pp who say it may be a way into controlling behaviour, but do you trust yourself to keep seeing him but keep your eyes open and take things very slowly? Be wary of any kind of fast-forwarding, future faking, love-bombing and possessiveness and watch how he conducts himself- does he message you regularly but not too often? Do what he says? Accept your autonomy? How does he react if you tell him no?

How does he react when you ask him why he says these things? That will give you your answers.

If he’s genuinely insecure he’ll be worried he’s upset/offended YOU. If he’s self-absorbed he’ll get defensive and try to turn it back on you ‘not taking a joke’.

My gut feeling is that shy/insecure guys don’t fish for compliments in this way (‘I can’t believe you think I’m good looking’ comment), in case they don’t like the answers - they haven’t got the emotional resilience to cope with negatives so would rather not ask the question in the first place.

Hm. The looks thing I wouldn't be overly concerned about. Perfectly 'normal' people have their self esteem issues, there are also learned and cultural reasons behind self deprecation. My most handsome male friend is from a culture that can't accept a compliment. He will insist he looks 90 and his immaculate outfit is falling apart if complimented. It's very endearing really. This aspect, I would let him get on with and not take too seriously for now. Don't get into showering with extra compliments or providing therapy. You could always say once quite firmly, 'if I compliment you, it's because I mean it'.

The 'clingy' point is a bit funny. I don't like negativity about women in general when dating which this feels a bit like. Clingy isn't one specific thing like 'i find it so rude when people keep cancelling dates last minute', it's just kind of suggesting that women have a tendency of buzzing around annoyingly and ignoring cues. I would challenge on this one. Maybe ask what 'clingy' means to him and does he know any clingy men? Ask good humouredly. Reason why, it feels a bit like setting a precedent for him being the one to decide the pace. Maybe not deliberate or even correct but I think worth asking about.

He sounds an interesting man, maybe a bit of a complex one. Everyone has flaws, you don't need to write off straight away but I wouldn't ignore the bits you're unsure of

Call me a cynic but I would be concerned that rather than being insecure he's actually setting the scene to be controlling and manipulative. Telling you he hates clingy women so that you don't feel like you can ask to spend time together, asking if you met anyone else on a night out so you don't feel like you can talk to anyone else and constantly saying he's unattractive so you shower him with compliments. I met a man like this, he came across as vulnerable and lacking confidence, the reality couldn't have been further from that.
Just keep your eyes open and be aware the phrase wolf in sheep's clothing exists for a reason. Good luck!

Hear hear!

Plus he wants to spend an inordinate amount of time together. Great in the honeymoon period, not so great later when you have to be reassuring him constantly you're not off spending time with that 'better man' than him.
Sounds like this will become utterly exhausting, prettysoon.

He is insecure. You will be needed to reassure him make him feel good about himself. That could get tiring but equally as the relationship progresses he may become more confident in it making it a non event.

Things I would look out for are-

How does he treat you? Does he return compliments/make you feel better about yourself too?

Can you be honest with him? If he's irritated you or done something you're not keen on do you feel able to address it? Is he able to acknowledge when he is wrong?

Is he comfortable with you having your own space e, time to yourself or with your friends and family? Is he worried/jealous when you go out without him?

Is he possessive of your time? Does he want to know where you are, what you are doing all the time?

Do you feel you can say no to him?