How to tell if a situation wants to be more?

Anonymous

Basically I'm new back into the dating pool. I'd been In a long term relationship that ended after 7 years. It's been a bit of time and when I met my "situationship" I wasn't really looking for anything. We were just friends at first but then one night one thing led to another and we messed around some. We had an agreement that we were just messing around, it was all good and well. But I'm getting hints of more from him?

To start there are ofc the good morning/goodnight texts, every single night. He never misses a one. Which ain't much I know, but if he has time he's talking to me all day when he can (which isn't often, his Job does keep him very busy but on weekends his focus tends to be on me and even when he's been at work from 5am - 8pm he'll still carve out time to talk to me for at least a little)

It's not always just sex. It's a lot of time just cuddling and talking. He's not seeing anyone else either we had a convo about it, he asked me if I was talking to other dudes and I said no (I had been but stopped shortly after we regularly were messing around. Not because I expected more from him, I just don't have the time to entertain more than one situationship, too much work.) HE then admitted he'd not seen anyone since the first time we messed around, and while he didn't say he WOULDN'T mess with someone else, I don't know he kinda hinted that he wouldn't? Plus there is a girl he was seeing casually before me that I know of and based on some nasty messages she's sent to some of the people who run in the same circles as me, he is telling the truth about not having seen anyone else

I guess I just don't know what to think about this? I'm not typically one to sleep around or get into these situations, but according to my friend she says this is turning into more based on how he's acting, but she thinks he's hesitant because there IS an age difference. I am 26 and he is 44.

How to tell if a situation wants to be more?
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