Is This a Lesson in Futility?

Met a guy 1.4 yrs ago. Had the usual 4 month chemistry attachment where he chased me until I caught him. Then he blew hot and cold. Goes back to ex-gf periodically. Toxic relationship.  When he's with me, he never wants to leave me. When he leaves me, he never comes back. Keeps contact mostly thru emails/FB. Hadn't seen him in 3 mos. but went on date last week where he says that he feels a great connection with me that he doesn't feel with others. That the fact that we are still sitting across the table from each other says a lot. That having the similar backgrounds that we have is very important. Then he doesn't call again but is receptive if I do, whiich is very infrequent. He is extremely insecure - too much to explain -  but asks questions like - what if  I find him boring later on, what if he's not really the funny guy I think he is. Do I ever worry that I wouldn't be all that to someone? (that answer is no) My question is: Are there men who need a little reassurance and the woman to be more assertive or is that considered chasing? Do I back off and just let him come to me? Does the squeaky wheel (not nagging or aggressive wheel) get the oil? He seems to care about me when he's with me and we have wonderful dates for hours and then he'll disappear for weeks. If I call, he's happy and receptive. He is used to women calling him and I'm used to being pursued. We are both in our 50's. Is it ever okay and at this age, to be more assertive or does that come off as needy? I feel that he and I are searching for something we've already found but are too afraid to show our vulnerablity. I have never felt this great level of comfort WHEN I AM WITH HIM with anyone else. We haven't slept together in months and he doesn't use me for a booty call. The fact that we've been on 6-7 dates with no sex bothers me too. I don't want the sex as he hasn't deserved it but the fact that he hasn't tried either bothers me. The more I write this, the more I think I should just move on. I do date but it's not the same with others.   I thought this would get easier with age but I've since learned otherwise. Thanks

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