McCree Romance Headcanons


Liking Someone:

– When Jesse likes someone, it doesn’t take long for them to find out, mainly because he will tell them. He’s comfortable with his emotions and thinks it’s for the best that he is upfront with it. It’s a way to stay true to yourself. Even if he knows the feelings are unrequited, he will still be open about it. He refuses to find shame in liking someone.

– He will flirt. A lot. He may not mean anything by it, but he likes getting his feelings across. He intentionally says bad and/or stupid pickup lines all the time to try to see that gorgeous smile that he loves. Jesse will use it to try to lighten up a situation. He stops flirting with others so much to let his crush know that he’s serious about them and what he’s saying.

– Just like Gabriel in his Blackwatch days, he will get his crush things. But while Gabriel giving them little things out of convenience for them, Jesse will go out and get more expensive things. Yeah, you may not have needed this necklace, but he’s sure it’ll look great on you. He tries to make it clear, though, that he’s giving them the gifts because he wants to, not because he’s trying to make them feel pressured into a relationship with him.

– He will try to impress them. Always. If they start mentioning how they think Jack’s tactical visor is cool, Jesse will show off his deadeye. And he don’t need no auto aim to pull it off, either. If they are fighting together, just know that he’s going to get compromised because he rolled in behind enemy lines to fan the hammer on one of them while his crush is watching.

Dating Someone:

– If you actually say yes to the cowboy, the flirting will not stop. If anything, it just gets worse. He even starts writing his own and will have his significant other rate them. Jesse makes sure to say them whenever they look even slightly disappointed. It may start a trend within the group to have people say pickup lines to them and have them vote who’s was the best.

– A lot of dates are at home. He’ll pick up a nice cake and some wine that they like from Walmart and enjoy them with his significant other over a movie on Netflix. Cuddles are mandatory. Jesse calls just about everything a date. If you ask him, the show that he took with his significant other this morning was most definitely a date.

– He would love if his significant other would do his mercenary work with him. Jesse loves the idea of the kind of romance where you two can become the infamous duo and never lose passion for each other. He would also be reassured by the fact that his dangerous lifestyle wouldn’t push them in harm’s way, especially harm that they couldn’t handle.

– He can be extremely insecure sometimes. He feels as though his entire life is a fuck up. He was in a gang when he was a kid, never completed high school, was a part of the torturing and assassinating Blackwatch, and is currently a mercenary for hire. He has a sense a pride from it, but that’s a front. He’s really just ashamed. Jesse will act out because of these insecurities. He gets jealous easily because he doesn’t know of a good reason why his significant other is with him when they could get someone so much better. So many people have left him for someone better, both romantically and otherwise.

– Fights crescendo. Quiet at first, but by the end, there is shattered glasses on the ground, throats raw from yelling, and tears from both parties. After not talking for a couple of days, he’ll show up on their doorstep with a bouquet of flowers and a shy smile. Maybe a gift if it was bad. Jesse will tell them that he’s just scared of losing them which is why he acts the way he does. If they keep up rejecting him there and tell them to leave, he’ll shed a couple of tears then dive head first back into mercenary work, trying to make his grandiose confident cowboy act closer to who he is truly again. Then, Jesse would take all responsibility for the fight and for his actions and actually apologize.  

Friends with Benefits:

– It’s easy to become friends with benefits with Jesse. There is really only one step to ensure a place in Jesse’s bed (and sometimes heart): ask. That’s seriously it. Sometimes, he’ll take it upon himself to ask his potential lover. He just takes his pleasures where he can get them, and he’d be more than happy to share some of those pleasures with you.

– He mostly won’t want to turn his friends-with-benefits into a romantic relationship. Jesse generally has a few people that he sleeps with, and not to mention that just because you get on well with someone doesn’t mean you’ll be good with them. If his lover becomes adamant about being romantic, he will just call it quits with them altogether. Being friends with benefits is about having a good time, and feeling pressured like that isn’t what he wants.

– If you had to describe sex with Jesse McCree in one word that word would be Kinky. He wants to try everything, he’s willing to try everything, and it would surprise no one if he’s already tried it all. He’s fine with all sex, from the hardcore slavery of BDSM to gentle, loving, kissing-heavy love making. Jesse also likes to switch up who tops often. His lover would need to be willing to be pretty versatile because one type of sex tends to tire him out more than the array of kinks he has stored away.


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