I'm 36f and have been seeing a 36m for 8 months. Previously I dated quiet, nerdy, shy guys. The current boyfriend is jokey, extroverted and a bit nerdy.
In the early weeks he made a few jokes that hurt my feelings. For example we were making porridge and he joked about "stirring the porridge". When he realised I didn't know what this is he explained (it's a thing from porn). I got upset and said I don't like porn jokes. I explained to him I thought the joke was gross and my first boyfriend was addicted to porn and made me dress up and act out things from porn which has left me with bad feelings about porn (I've recently started therapy to help with this). He was apologetic and said he was only joking and didn't mean to hurt my feelings and that he understands that I'm sensitive about this.
Another example is he told me he went to an office party at his new job where everyone was drunk. A short woman colleague said "you're so tall!" and he told her he once had a much shorter ex girlfriend and they couldn't have doggy style sex because she couldn't walk the next day. I told him I thought it was inappropriate to talk like this to a woman he didn't really know, and also it sounded a big braggy and blokey and I didn't like it. He said he understood why I felt this way and apologised.
Another time we were having a few small cakes and I said the cheesecake was nice and he said "women like cheesecake". I got upset and said even though it's a minor stereotype, even small stereotypes are part of a bigger issue and divides us into an "us and them" mentality and where do you draw the line, women aren't good at maths or science or driving, etc. He was understanding about it.
He plays video games with his friends and his friends make a lot of jokes about porn, blowjobs, raw dogging it etc. It's mostly other guys but there's one woman friend but she's quite laddy and takes part in these jokes too. He has been really understanding when I explain I don't like these jokes and he has cut down on them a lot (around me anyway) and says I'm allowed to be sensitive about this issue and that he would never want to hurt someone's feelings with his jokes, but it's tricky because his friends and family seem to all be like this and I'm not sure he will stop speaking like this with them and I'll get upset when I'm around them but I won't say anything because I don't want to come across as "stuck up" or lame. Him and his friends also do a lot of toilet humour which I don't like but I haven't yet mentioned this to him.
He is otherwise very kind and he listens to me, tries to understand me, is supportive and really fun and interesting and smart. He says he thinks I'm the one and he would like to move in and one day get married and have children.
I feel like I'm being too picky and judgemental and unreasonable with him. He's bent over backwards to stop making these jokes but I'm anxious about it all and just worried I'm changing him and I can't relax or trust him or fully commit. He says he wants to change and my points are reasonable. My family and friends all really like him, I'm not getting any younger and have dated lots of guys and found dating quite stressful as it damaged my self esteem with so much rejection and wishy washiness. So finally I met someone who seems to like me and wants to make an effort to have a relationship and fundamentally seems like a good person and I feel annoyed at myself that I'm struggling with something so superficial as a sense of humour and that I can't seem to meet him half way. My friends tell me nobody is perfect and I should compromise. But I'm just not sure I am strong enough to deal with this, or if I'm over reacting. I'd be grateful for opinions, or advice on how to deal with this, thank you!