Search Results: rejected by friend

Sorry this is long. Basically he messaged me on Okcupid, says that I’m really beautiful, we’re in each other’s age range (I’m 36, he’s 41 and says he wants a girl my age) and supposedly I have everything he was looking for in a woman. The problem was I really wasn’t feeling any interest for him after reading his profile, and he lived to far away from me (I’m on Long Island, he’s in NYC and kinda want someone who is also on the island that I don’t have to commute to date). I sent him a polite message (that’s very sweet of you but I don’t think we’d be a good match). He sends me two long paragraphs in return saying he doesn’t understand, that I should give him a chance, that I might change my mind once I get to know him, that I’m already 36 and not going to get many more chances then begs me to reconsider because he wants to leave the city and saw getting involved with someone like me as the perfect escape from New York, that he wanted us to pick out our future hometown together and said that he was really shocked because I sounded so nice in my profile. I apologized again, told him not to send me anymore messages and blocked him. So tonight (about three weeks later), I get another message from him (from another account he created) telling me he still really wants to get to know me, he still wants me to get to know him then gives me his phone number and begs me to call him because we’re both on that site looking for partners and he could be the “perfect partner for me but I don’t know it because I’m not giving him a chance”. I told him to stop messaging me and leave me alone. I was with two friends when I got this message. One told me that I did the right thing because he sounded really desperate and the other friend told me that I’m not getting any younger (which I’m not) and he sounds really interested. She says I should overlook the differences and the distance and date him, so now I’m feeling really bad. What do you all think?

I've been on a lot of dates, but I've never been the one to ask a guy out. I'm more of a shy person so I've honestly never even tried and I'm terrified of it. I prefer the process of getting to know someone and becoming friends with a guy first.
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But I pushed myself and I've approached a few guys before to make conversation and some of them got the idea that I liked them but their attraction would wear off because they didn't ask me out. I felt that maybe it was because they generally weren't interested or just sensed that I wasn't really being myself and wasn't putting myself in a position to be pursued. Sometimes, guys digged that but then they only wanted sex from me, so then I reject them because friends with benefits is not my thing.

You know what I find odd? Men keep saying that they love the chase, yet sometimes they don't pursue and are expecting a woman to make the first move. I just think that's kind of cringe because I prefer to be the one who is pursued and 99% of the girls I know do too. I've noticed lots of guys might be enticed by this kind of girl at first, but then they move on to someone else who they want to pursue. *Basically they think the girl who approaches first just wants to suck their dick.* What's your opinion on the chase?