Would these comments and behaviours be reasonable deal breakers in dating?

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I've was dating someone for a few months (met on Hinge, mid 40s)and am reflecting on my standards and self-esteem in the wake of it ending. Which, if any, would be deal breakers or have caused you serious concern?

-made a few silly sexual jokes whilst messaging, before we met eg..I asked him if he played a musical instrument and he made a joke about wanking
-first date in a coffee shop, I removed a long sleeved top as was too warm (had another top on underneath obvs) and he went "wahaaayyy" as if I was stripping
-made a joke about all women having a base level of psycho
-referred to disabled people as "Scopey"
-met a colleague of min at a works do and told me she was "rough" and this is why he doesn't date women from her area
-despite the fact he is on amicable terms with his ex wife, told me laughingly, when she asked for a divorce, that he had called her a "fat old witch" and threatened to take her pension
-told me inappropriate details about his ex including that she was restricted in sexual positions she could do due to bad hip and that she could orgasm immediately from anal sex (he told me this whilst we were in bed by way of praising my comparative flexibility)
-said "You look lovely in your dress; my ex wife never wore them because of her body type"
-met an acquaintance of mine and said "You're naturally beautiful, not like women like that who plaster on the make up"
-when I was trying to encourage him to get o know me better and asked if there was anything he wanted to know about me (cause I had tried to ask him lots about himself) he said "What is the smallest penis out there have encountered?
-told me, in bed, that he had yet to encounter a smelly vagina
-told me he had dumped a woman as her pubic hair was too long (after avoiding having sex with her for weeks)
-shortly after we began a sexual relationship, told me he thought genitals in general were gross and then was annoyed with me when I went a bit quiet and distant for a few minutes after he said that
-first time we had sex, he seemed clueless despite being married before and many relationships. He kissed me for a while and I was expecting some foreplay (I know I could have initiated this but I had lead on taking him up to my bedroom and removing clothes so didn't want to lead ointment everything). Without so much as touching me intimately, he entered me without a condom. He stopped as soon as I told him to and was visibly upset and said he thought I had wanted it as we were naked and he was laying on top of me. He was genuinely upset and I ended up comforting him!
-I disclosed to him that I had been sexually assaulted in a previous relationship. Despite this, he sent me a GIF that appeared to be of a woman being assaulted, face down on the floor and crying..looked like really rough porn but you could only see her face.
-he had some very laddish mates and he said he didn't judge them for sleeping with prostitutes although it was not something he would do. Told me they had all been giggling in the pub about some story about a woman with a massive anus.
-in a weird coincidence, a mate of his turned up at my house to collect something I had listed on marketplace. He arrived 15 minutes earlier that agreed and ex and I were in bed. When ex realised who it was, he got dressed and said hi his mate. he later told me that the incident had been the subject of joking on their group WhatsApp, with one them writing "He was just pulling out of her as he arrived!"

I felt unsettled with him lot. Would the above reasonably explain that? I have very poor self esteem and anxious attachment style and I am trying to work out if there were reasons outside of that which would make others feel insecure in this dynamic. He was affectionate, attractive, a good dad, good to his mum, a professional, kind to animals, funny, lots of friends and very keen on me. He would send gushing messages and romantic songs and GIFs a lot. He seemed quite future -focused with wanting to progress the relationship quickly. He made me feel very chosen. He was not the type to ask me things about how many men I had slept and liked natural-looking women. So there were lots of good things about him too.

He 'doesn't feel good enough' because he isn't good enough. He's a sad little creep.

I spend a good few years between husbands and during that time, just one of those things you mention in your OP would have meant that a first date would be the last.

Do others agree there was no mitigating the rape GIF even if, when he sent it, he was feeling annoyed with me or having doubts about us? I had not done anything more than calmly ask if we were ok after an arguement and a week apart. He seemed to view that as me questioning the relationship and was clearly irritated with me .

There are no circumstances under which it was ok to send that to you.

Why did he break up with you?

There is no mitigation at all.
It is an act of visual violence which a victim of SA opened on her phone without expecting it and was traumatised.
Honestly, I’m starting to bang my head against a brick wall here. Surely you can see that?

There are no circumstances that would mitigate anyone sending a rape GIF to anyone at all, let alone woman you proclaim to want a relationship with.

A man who sends something like that is scum. There is no justificaton that would make him not be scum.

Because he felt he wasn’t making me happy and I got emotional a couple of times. By emotional, I mean eyes welled up slightly as opposed to bawling, shouting etc. this made him feel not good enough .

The second time was after he had sent me the GIF, later that day. I had some bad news about a loved one, he was cold with me and I got teary.

I am glad he broke up with you. It’s the only thing he ever did that will help you.
Please seek some therapy to get some help because I have a feeling none of us are getting through.
And all this crap about not being good enough/making you happy. Well, technically it’s true but he sounds pathetic.

And if he told you the sky was green would you believe that too? He’s coming across like a sleazy numbskull, who cares what he thinks? His judgement is not to be trusted.

There is absolutely no mitigating it and if anything it makes it even more sinister that he sent it to you when he was annoyed. It is a violent image and he wanted to scare you.

Please block all communication with him OP and never see or speak to him again. Thank goodness he is out of your life. He has potential to get very nasty

So why he actually broke up with you is because your focus was on something else other than him and he didn’t want to be the one supporting you, he only wanted to be the one being supported.

You’re bloody lucky he’s not tried to come crawling back. I can only assume he’s found another victim to suck the life from.

It didn’t quite go down like that but he found my tears overwhelming and an indication that I was too much. I felt awful about the evening for ages but can now see that it was understandable i got upset under the circumstances.

Of course it was. Perfectly valid to be upset when you are worried about or hurt about a loved one.

But narcissists don’t like it when you have feelings like that because it means you are distracted from them. It also highlights that they have no real compassion.

So they try to tell you your feelings are wrong and that there’s something wrong with you for having them. That you’re too sensitive or overreact or whatever.

When the truth is they are pissed off at you at that moment for being a human instead of a girlfriend appliance.

any single one would be a deal breaker/ick but I didn't get beyond about 5 of them before getting to the 'why are you even asking, you know they are' point

He's gruesome. Absolutely gruesome. There is never, never EVER any mitigation for a rape gif. He was deliberately exploiting your pain in the cruellest way. For kicks. He did it because he wanted to hurt you. Imagine what sort of subhuman you have to be to do that.

Quite the contrary - it was a deliberate and vindictive attack upon you. He was getting the boot in as part of breaking up with you because he didn't like the challenges you were so rightly making. Honestly, the more you describe him the worse he gets. Even if he believed you were 'too emotional' for him (which is how he wrongly perceived you setting any boundaries) a good man would have said, 'This isn't for me but I wish you well, I hope you feel better about xyz in time.' He broke up with you in a highly abusive manner regardless of how nice he is to his mum or puppies or whatever.

Jesus wept.

He got angry because his FuckMaid 2000 actually became human for a moment at receiving some bad news?

The only shame you should be feeling is that you didn't break up with this utter wankstain on humanity first.

There is no possible mitigation for that behaviour. It is indefensible.

He's vile. Dump him.

I’ve been thinking about this. Once I told him to stop and said we should have talked about condoms before going this far, he immediately stopped and was mortified. As I said, I consoled him. He messaged later and did say he had misread the situation and wasn’t a selfish lover and made quite grand claims of what would happen next time. The claims didn’t materialise and I do think he just lacked natural sensuality really. However (and im really not proud of this) a while later, we attended a party and I drank too much. I was clearly intoxicated (not usual for me) but we had sex in my house, downstairs with the lights on. I don’t remember it all. He was much more sober. The next day, he was going on about how funny it was because the blinds were open and lights on and I was really worried that the neighbours may have seen. My home is meant to be my safe space and it is important to me to have good relations with neighbours so I was really worried. He just found the whole thing funny. Whilst I absolutely take responsibility for getting that drunk (I know I should know better), it was another incidence of me not feeling sexually safe with him on top of the awful first experience and comments about genitals .

So he was a really mixed bag of qualities and issues, as am I.

I’m interested in why you place so much weight on the ex-wife’s opinion. Ten minutes of reading mumsnet will show you that women get men wrong all the time, and stay enmeshed in situations when they shouldn’t all the time, and speak kindly of men that are fucking them over in every way All The Time.

Ex-wives should not be your litmus test. Learn to trust yourself. Again, I recommend the freedom programme.

I felt sick reading your update, like throwing up sick.
He is not a mixed bag of qualities.
He has none.
Again he knows you are a victim of SA and slept with you when you were drunk, in your safe space with the blinds open? And thought it was funny?
That is absolutely sick. If you can’t see that then I’m not sure how much advice can give.
I hope to God this thread isn’t real, because if it is, I feel absolutely sickened by this man.

You really need therapy, OP. And not to date.