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I work in a big company, where I have one coworker, which always makes me feel really uncomfortable by his constant jokes with sexual connotations. I see this coworker in breaks or when having lunch and sometimes also outside of work, because we are in the same group of acquaintances and friends.
These jokes are mostly not about me and I don't think these jokes are hostile or meant to hurt me. I'll give you some examples:
when talking about a new app idea, that has something to do with mattresses: "It could measure the pressure, when she is on top of him or he is on top of her ;)"
when we play table football and i say "Yes, yes!" to indicate we are going to get a goal: "You are going to get an orgasm, huh? ;)"
when talking about possibilities for someone with sleep problems to fall asleep more easily: "Sex definitely ;)"
I'd say 20% of the time he says these jokes to everybody around and the rest of the time he kinda "winks"(this is the wrong word, but i find no better way describing it) at me to let me know this was directed at me or something.
This makes me extremely uncomfortable - to the point, I'd rather not talk to that person, if he continues. I usually react in a way to try and show that i do not like this non-verbally, e.g. raise my eyebrows or look frustrated, but this obviously does not work.
The thing is, i have had a similar conflict with this person before, where he would tell me really graphic details about his past sexual encounters and i told him to please stop this. He actually did.
Now i could talk to him again, but i have really mixed feelings about this...
Is his behavior really crossing a line?
Is this just "who he is"?
How should i approach him, if i do?
Will it not just make any contact so awkward, that it's just easier to try and not have contact?