Should this Cancer Make the First Move?

This man who I've known for quite awhile expressed an interest in taking me out several months ago. I offered my number and didn't hear from him, though I saw him weekly at our open mic poetry night. He was always friendly and flirty during those nights, and mentioned going out to dinner several times.

Finally, he did call, at 11pm. He wanted to meet up at the local late night eating spot, but I had to work in the morning so I said no.

It wasn't a booty call, I'm certain of that. Doesn't matter that it looks like one, I just don't think it was.

I was afraid he would see it as an excuse so later that week, I gave him the bright green light and told him to call me earlier for dinner if he wanted to go out. I have 2 jobs and need to plan for things like that, he said he would, gave me a nice hug - and NOTHING!

So, this past week, I am thinking - okay, this guy isn't into me that much, okay fine. I'll be friendly, but I'm not making a fool of myself for him. On my way out, he offers to walk me to my car and tells me that he'll call in the next couple of weeks "when I have some money to take you out." He kissed me really sweetly and we said goodnight.

This is my question - I don't really care if he pays for everything, if that's what's really holding him up. But I don't want to immasculate him by saying that...it seems important to him. Do I tell him it doesn't bother me? I'd rather just go out than worry about all that...

AML sounds taken or married to me, from my own experience when men stall it's a red flag that leads to something along those lines, IMO 11pm is bootycall, ain't nobody calling that late for dinner and coffee there are few exceptions to this rule, it's disrespectful, it's not a great way to start off getting to know someone by calling at 11pm, I don't say this to anger you or accuse him and I wouldn't encourage you to defend someone you really don't know, look at his actions not his words, his actions say I'm not interested in you enough to move forward, if he's already complaining oops mentioning he lacks money to take you out that's another red flag and if he can actually go there then he's not worried about leaving a good impression because if he was into you there is no way he would let you know his problems so early on, his behavior says I like you but not enough, you deserve better than that, I would keep it moving, not make it so easy to get next to by offering up a meeting with him....You have made it clear your available, you have done enough, lean back and let him show you he's interested, so far he's fallen short.

If you just want a project, some fun, some drama, an intense thrill hey go for it but if your in a space were you want something real....keep it moving

Also if you don't want to be the one footing the bill all the time, leave the money issue alone, in other words paying his way will make him feel emasculated whether you want him to feel that way or not and if he doesn't feel emasculated he's the typical man-boy that doesn't mind being taken care of and you will never get your share out of him because it will be about him and his needs, not a good way to start off getting to know a man.

Let him figure out how to date you, if it takes him weeks to get up some dough to carry his weight than so be it, don't be desperate to fill in the gaps and voids to HELP him date you because if you do your inviting neglect and mistreatment into your life, paying will give you a short term effect but will have a negative longterm impact...If it were me in my younger years I would most likely go on and fix it and pay because of my desire to go out, only to regret it and end up feeling used and neglected in the inevitable end, you don't want that kind of experience if you don't have to go through it, be patient, he will figure out how to close the gap and get near you if he truly has the desire.

You're very right Tiki! I didn't contact him at all, but got a text from him asking if we could do something together on Sunday, and lo! he called and we went to the park and walked around for a couple of hours talking and getting to know each other. It was pretty sweet, didn't cost a dime, and he was a gentleman the whole time. Dropped me off at home at a decent hour and asked if I'd like to do it again sometime.

Patience paid off, let him move things forward, he can and he will if you lean back and let him and your worth it.

Well...I've ended things with him. We went out the one time and he was slow to ask me out again...I have no idea the motive.

Also, he is 30 years old and lives with his mother. He doesn't have a job. I just can't see a way around this, so I broke it off. He seemed surprised, which surprises me a bit.