in a lot of ways jackie will never be able to have nice romances cause a large part of him actively regrets it when he does. not in the sense he regrets the relationship but rather regrets what he has to do for the relationship to work. his whole thing with jenny within the video games at times holds a very secluded and separated from the rest of what is going on feeling within them, the first being cause he almost has to think of his life as a hitman as being something far removed from him being jackie, jenny's gruff yet loving boyfriend, and the second cause...well....he's literally being haunted by her ghost lol. he keeps his 'day work' vague when speaking of it with her, keeps the things that happen come his succession to the darkness a secret from her, he acts only as one half of who he is for her. it's things like that that make me not a huge fan of jenny/jackie cause she is firm in her stance of never being able to love him as himself within the comics, while in the video games it's more toned down and they are treated as what they always will be: a tragedy of first love.
jackie can lament the way he lives all he likes and claims he isn't the man he clearly is (cold, emotionally distant, isolating & cruel by a nature he can not deny), but it's not a healthy thing and it only gets exacerbated when he tries to make it work with jenny in mind. he knows he's keeping secrets from her, he knows he's doing things she doesn't like or agree with on a fundamental level, he knows he's only being one forth of who he is with her just so he can give her the illusion of a nice, healthy and happy relationship. it's due to that forced conditioning and thinking that i don't think romance is easy with him nor a thing he really desires. one of the few positive traits jackie has is that he's a very honest man both with those around him and who he is as a person. but when in romantic scenarios he falls into a kind of trap of trying to be someone better than who he is and it eats at him from inside as he puts the other's wants before his own.











