To be concerned about his insecurities?

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?

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.

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!

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

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.

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?

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.

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

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.

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

I really wouldn’t like this.

Is he dropping hints that you two are not compatible or anything?

Be wary OP. Had a similar experience, in the end turned out the guy was basically love bombing, his "insecurity" was his way of pretending to be vulnerable and I assume get me to want to reassure him/feel closer. Want to take care of him. Also very handsome but constantly asking me about other guys at the gym he "thought were hotter than he was" (we met at the gym). Whether I'd met anyone more compatible, getting me to say no. Extremely manipulative.

He dropped me extremely suddenly when he realised I wasn't going to move in and pay his rent/ask him to move in with me, and got back with his ex who he had 0 respect for but would at least pay his rent for him. And when I say suddenly, I mean suddenly. One evening he was telling me he had never felt this way before, was addicted to me, wish he met me years before (whilst also complaining that he couldnt pay his rent since ex has moved out, trying to get me to go over there, me saying no kinda thinking he was joking)... literally the next day, told me it wouldnt work and dropped me. Day after, saw him in town holding hands with the ex.

I'd be less worried about insecurity and more worried about being manipulated. I was totally drawn in by him to at the time, falling very quick... but not quick enough for him due to me not wanting to move in together after a few mere months. I was getting sucked in, but not quick enough for him.

Does it ever feel like he's putting you down for saying he's attractive? Or trying to mock it? Whilst also seeming to need the reassurance?

Is he just very confusing?

Seems very keen on you and yet somehow makes you feel shocked that he is?

How "lucky" you feel to be with him is a bit of a red flag for me too.

Just be careful and wary.

The behaviour is unattractive, whatever its cause! Particularly badmouthing ‘clingy’ women. I like plastictree’s suggestion.

It’s presumptuous to suggest that he ‘should’ think / say / feel about himself based on his looks, job, initial behaviour in your relationship or whatever. You don’t know him well.

Depending on how much I liked the person and what else was going on, being totally honest, I probably wouldn’t continue with it personally.

My sister was in a similar situation and the jokey “have you met someone better yet” quickly became arguments and accusations because “I know you wanted that man who walked past you in the veg aisle at Asda, don’t look at other people” and “you obviously fancied the bloke in the post office because you asked him for a stamp, don’t speak to men”. The “I’m not clingy, but I want to see you everyday” mixed with the insecurity about appearance and other men quickly becomes “send me a video of where you’re sitting so I can see who is on the tables around you”, deliberately picking fights when you have plans so you are forced to stay in while being able to keep you in your place when HE wants a night out as he can remind you he hates clingy girls etc.

Thankfully that arsehole is now my sister’s ex, but I couldn’t be arsed with that!

Can you talk to him about it? What’s his dating history - maybe he’s had a dry run recently and so is lacking confidence. Maybe next time he brings it up, challenge him, and even say that that joke is getting stale now, so move on.

Regarding spending lots of time together, don’t let him move into your house stealthily.

Have you had sex with him yet?

Is it a crime to be insecure now? Have you reassured him? If you have and he keeps it up then maybe rethink.

I’m worried that this apparent low self esteem will be flipped around and used as a means to control you through guilt. Like ‘you can’t go to the pub by yourself, you know it makes me worried you’ll find a better guy’ or ‘there’s a good looking guy at your work and he’s a better match for you than me so I don’t want you doing overtime and I’ll start picking you up from the office…’ etc

These sorts of comments are definitely off-putting and it does seem indicative of low self esteem. Do you think you could bring it up to him in a nice way? E.g the next time he says something of that nature you could comment ‘I’ve noticed that you say this kind of thing quite a lot’ and see what he says. I don’t think it’s necessarily a red flag though, if everything is going well. Maybe he just can’t believe his luck! Hopefully he calms down soon!

I don't think having insecurities makes anyone a "fixer-upper", it makes them human.

I think for a lot of people, a relationship is the only place they can express their vulnerabilities, and that's incredibly important. Probably more so for men because female social bonding over looks-based insecurities is the default. I don't think men get to be vulnerable with other men over thinking they're not good-looking. (Add the fact that the conventional masculine ideal is narrow and rigid, but men have no real space to unlearn being tied to it as we do regarding the feminine ideal.)

Insecurities become yellow/red flags when they manifest in unreasonable behaviour: jealousy, territorialism, control over a partner's friendships, neediness. And constantly seeking reassurance would get annoying very quickly. I suggest OP cuts to the chase and actually talks to her partner about this pattern she's noticed. Let him get them off his chest properly rather than these constant little fishes for reassurance (and then nip those in the bud).

I was about to say the same as the pp. Cut down on the jokes and start talking. The jokes could be masking a lot.

My DH is quite insecure. I don’t mind at all or find it burdensome to reassure him. There’s nothing wrong with him, he’s just a sensitive type who had a less than ideal upbringing. But he’s generous and kind and supportive, and I’m lucky to have him. He cherishes and appreciates me. However the ‘did you meet anyone else yet’ questions would need to be firmly nipped in the bud! That’s going too far.

I love to have a good laugh with someone but I wonder whether you're doing too much joking around. Sometimes quite hurtful things can be said then because people are still trying to gauge what is a joke to the other person.

I'd watch and wait with this one. I'm sure reasons for any insecurities will emerge soon if you have good long chats about this past

To the poster whose husband was in care - that is absolute heartbreaking and I'm so glad he's got a good relationship now

Wow! Don’t we all have some sort of trait that needs to “fixed” - in our own eyes and in others?!

Ask him why he says those things about himself. Or reassure him and tell him
why you find him to be a good catch.

This would annoy me as well OP

Agree - I mean he’s not a house that’s gone into disrepair