He isn’t very assertive.... I’m having trouble because this guy I’ve been talking to is a very...

luckranger71 · 51-55, M

To use a baseball analogy, you’ve thrown some slow pitches over the plate for him to hit and he hasn’t swung. I guess if you want, you can be super blunt and ask him if he likes you.

But I would tend to think you shouldn’t reach out at all. If he’s interested he’ll eventually contact you. In the meantime there are plenty of other fish in the sea.

Keepitsimple · 51-55, F

Fall back. If the interest was there he would put more effort into you. You would know.

SW-User

I stopped chasing men. If they want you, they'll let you know for sure.

Reciprocate his attention if you feel it too, but what they say is true of everyone...If they want to, they'll find a way.

BananaBrown · 41-45, F

Be honest and tell him directly how you feel. You may be right, and he may simply not know how communicate his feelings. Worse case scenario is he is not interested, but at least you don’t have to keep guessing his intentions.

WildernessWriterExplorer · 31-35, M

You're looking at the issue as black and white and it simply is not that. Communication is key so if you want an answer you need to ask him yourself. Talk to him, see where his feelings are, and then reassess from there.
I had a friend in college who, his now wife, threw out so many hints and subtly and he just believed that she was being friendly and basically showing him pity. It wasn't until she said are you ever going to ask me out that he started seeing her as into him.
So don't lose hope.

MrsPeterEvans · 31-35, F

I would hate it if the man didnt take charge

Chevy454 · 46-50, M

Some of us are oblivious of the fact that you are flirting with us. For example, I was a bartender and my supervisor asked me over for dinner with another couple. We ate, had fun. I knew everyone there. She probably had them leave to be alone with me. They said they we’re leaving, so I did too. I was on my motorcycle, so when I got home I had a message that she was hoping I stayed.🤦🏻 It worked out and we we’re together for 4 years. Sometimes we need to be bashed over the head. In your case though, that seems to be kind of the point if you were texting or chatting. I think he dropped the ball a little bit.

HootyTheNightOwl

How does he see himself???

i am one of those people who doesn't believe that anyone could possibly be attracted to her and he's acting pretty much the same way that i do.

He might be more inclined to take the initiative if you are straight to the point and leave him with no doubt whatsoever that you are into him.