Is it normal i'm really bad with men?

I'm really bad with people, getting to know them and being open is hard for me, I joined a dating site and got speaking to someone who looked good, we added each other on snapchat and didn't really speak much until he sent a snap and I replied sarcastically. It went from there and I began to really like him. He gave me the impression he wasn't interested though because he would stop talking or never start first... so I kept sending snaps General snaps so it didn't look like it was aimed at him so he'd reply and then I'd go from there... he always replied in fact at the start he sent some shower ones and flirted like mad... and he never asked me for any but it went quiet after that. I asked him if he was shy and he said yes (like myself) I have kept trying well not really just sending snaps I haven't actually gone hello are you okay..
The other day though I just thought fuck it and flirted with him and I got a lot out of him we had a heart to heart about social awkwardness and it turns out we are a lot a like that way but he still never makes the effort first which makes me feel annoying... we got flirting and he sent some photos but I didn't send any back not nudes but just flirty ones and he stopped talking.. so maybe he thinks I'm not interested? But I can't just send a random bikini photo it would make me feel weird and he might not like that about a girl..
Also me being shy I hate getting to know people because I feel annoying but when someone makes the effort for me and tries to be my friend I like it because I feel worth it.. maybe that's what he needs from me? At the start I asked a few questions to get hints from him like ' we can be friends?' Hoping he'd say he'd like to get to know me more but he didn't I think I made it worse.. so now maybe he thinks that's all I want? But I don't at all. I once asked him if he'd found anyone but he said he'd been hanging out with someone from work but that's all it was. I can't work him out.
I don't know whether to ask or tell him how I feel once we start talking it's great but I feel annoying if I talk or flirt with him.
Any ideas ? I have kind of made sure we speak everyday for the past few weeks ... :/ finding it hard to leave him alone I'm not the confident type but I'm thinking leave him for a few days and if he doesn't message first then just go for it. Because some of the other guys who seem interested just keep talking and making an effort. But if he's not because he's shy I get that cause I'm the same even over text.