What’s the deal?

Question

So I was having casual sex with this guy for a while. We got on very well and messaged/called one another not just to organise to meet. Anyway I told him I wanted to end the casual sex because I just didn’t want to anymore but if he was cool to still be friends and hang out. So we have, no sex or anything. But he does keep mentioning it in a flirty/jokingly way that I’ll change mind and all that. As a joke back i said if you wined and dined me maybe I can let it happen once. And he goes “ I’ll legit do that, book a hotel room, dinner, and everything all my shout”. I laughed and said to him I don’t get why you would put in so much effort to have sex with me if it just was casual sex I’m sure you can find someone else willing to have sex and you can get the release you seem to be wanting and that I can’t give you. He proceeded to say he likes having sex with me and wants to. 
I’m definitely not being like Omggg so sweet I’m going to sleep with because you said that. But I’m just confused as to why he’s trying so hard when it was just casual and he could easily just find another girl to sleep with if he wants sex. Am I thinking about it all wrong??

Answer

I would guess it’s like a “he wants what he can’t have” type thing. Like views it a challenge maybe?

Answer

You both are throwing mixed signals. Are either of you interested in more than sex? Going from sleeping together to just friends is difficult. Being fwb and someone catches feelings is hard. 
If you could see yourself dating for real, I would tell him. If not I would cut off all contact for both your sakes

Answer

He enjoys your company, it’s a friends with benefits situation, don’t read further into it that he wants to be dating you or in a relationship, he just wants to get laid and he will do whatever it takes to get laid, like you said he couldn’t hook up with random people but he likes the connection he has with you, he enjoys your company, I’m sure you guys have good communication, maybe good sense of humor, etc. Never assume that somebody wants more, just because you guys act like boyfriend and girlfriend, sometimes they enjoy the benefits, but don’t want the commitment and responsibilities that come with it. I honestly would not read too much into it, and just take it with a grain of salt, and just take it one day at a time, and just go with the flow. But make sure that you both are still on the same page of what you want and what the intentions of the relationship is. And if one person catches feelings while the other one doesn’t, that person can end up feeling used and taken advantage of, unfortunately when feelings get involved in a relationship that’s not intended to be a relationship, it’s just having fun, friends with benefits or hooking up or whatever it may be, feelings end up getting hurt, you lose the friend, you lose a lover, some people can and some people can’t be friends afterwards because it’s too hard. Honestly just take it with a grain of salt I can’t stress that anymore. If he makes jokes and he makes comments, that make you say awwww. Take it was grain of salt, can’t stress that enough. Now he hast to Woo you to get you in a bit. Now he has to work for it, don’t think of it as a date obviously. It’s just a venue location, that’s it think of it that way different place. Two people sharing a meal, and having sex afterwards that’s it don’t read further into it.

What’s the deal?

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