I can think of three women that I developed an infatuation over that I ended up meeting years later.
Developing infatuation:
1) Hadn't even met her in real life. She showed up on a friend's FB timeline in 2008 (approx) and was physically at 10 in my books. Ticked all the right boxes for physical attractiveness for me. Creeping her profile only intensified the feeling of attraction as we shared a shit load of interests. Spent a couple months occasionally creeping her profile, considering asking our mutual friend for contact info, then, oh fuck, she's talking about graduation?! Still in high school, back the fuck away (I was 21).
2) A buddy's girlfriend in high school. He was a piece of shit and I was only friends with him because he threw great parties and sold me drugs at cost because he had a major man-crush on me. On his first day of middle school (junior high) I saw him constantly being bullied by some older students and one day I had had enough and beat the piss out of the three of them (grew up in a farm town, used to do labour work for my neighbour, was 6'5" by grade 9 when this occurred), so he thought I was the best person in the world. Anyways his girlfriend was gorgeous, was funny, and he cheated constantly on her. But, she was a friend's girlfriend, so off limits and didn't think anything would come of it.
3) Only 'knew' her through our city's forum on Nexopia from high school. Seriously one of the most attractive girls I had ever seen. Didn't tolerate bullshit, sarcastic as all hell, perfect. Awful lot of profile creeping back in high school.
I should take this time to point out that after high school I got a job working in construction which caused me to lose my fat and gain even more muscle. I also cut my past-my-nipples hair off, started trimming my full beard, and learned how to buy clothes that fit properly. At age 23 I was 6'5", 290 lbs of muscle, dressed decently, and had a big beard. I was suddenly quite attractive, but I still hadn't realized it.
Meeting years later:
1) The shortest gap between forming a crush and meeting one. I was 23 and hated going to the bar (still do), but a lot of my friends were hard into the bar scene (BC, so legal age is 19, important). I was doing my standard standing in a dark corner of the patio, chain smoking cigarettes, and looking at my phone counting down the time til closing and we could go back to the house to keep partying in an atmosphere I was comfortable with. Suddenly I hear a female voice, "Hi!" and I look up to see Dream Girl #1 standing there smiling at me. I'm too stunned/nervous to even reply, she waits a bit, then asks for a cigarette. Give it to her, finally am able to talk and we chat for a bit. I'm trying to work up the nerve to ask for her number when a VERY drunk friend comes crashing into me, yelling about how one of our buddies just tripped and tackled a row of tables, and that we're all being kicked out. I look around, can't see her, leave with this cockblocking fucktard. As I'm about to get into a cab she comes charging across the parking lot, "WAAAAAIT!", grabs my phone out of my hand, and puts her number into it (she was very embarrassed about this later cause she was very drunk and never approaches guys at bars, let alone charge across parking lots at them. I can confirm this as you'll shortly find out.) Fun fact: We actually ended up at the same house party after the bar, I just never actually got into the house cause it was so full and just stayed in the yard.
Anywho, we texted for a couple weeks, hung out once with nothing happening (even though she asked to come to my place and asked if she could stay over, slept in my damn bed with me while I lay there all night trying to work up the balls to make a move) and eventually hooked up while on a camping trip with mutual friends. She was moving across the country for school in September, so we knew it wasn't going to last beyond the summer, had a great few months. We stayed in contact and have been pretty much best friends for the past five years (with only one drunken make-out the first summer she came back).
2) Ran into her at a house party five years after high school and I hadn't seen her since. She confides to me that she always hated it when I came over to her bf's place because she was always worried he'd notice her infatuation with me (wut), and then gives me her number as her friends are leaving. Fun fact #2: This was almost fucking exactly 24 hours after getting the number from Dream Girl #1. I had a choice to make and went with #1. Scumbag move: I waited for about two weeks after #1 and I had decided against something dumb like a long distance relationship and she had gone off to school, called up #2 and apologized profusely for not contacting her earlier and that my summer had just been way too busy. Quickly found out that she was actually quite dumb and that I couldn't stand her unless I was drunk. Luckily (not really), I was drinking way too much at the time so it didn't interfere too badly.
Couple weeks of dating and hanging out, she finally jumped on me one night when we were drinking at my place. I made it clear before things progressed beyond kissing that I wasn't interested in a serious relationship and I guess she took that as a challenge. After a month of her showing up at my place for sex, she put her foot down, "We're not hooking up any more unless we're dating." I shrugged and said, "Ok." So she yelled at me for a bit and left. A few days later she texted me asking if I was home and if she could come over to drink, "BUT NO FUNNY STUFF!" and I replied, "ok." She came over, we got drunk, I told her she could take my bed and I'd stay on the couch, so she got naked and climbed on top of me. The next morning she'd bring up the topic of dating, I'd say no, she'd yell at me and leave. This was the pattern repeated for four months: she'd ask to come over with the caveat that nothing was going to happen, we'd get drunk, she'd jump on me, we'd have amazing sex, then she'd yell at me in the morning and leave. I was never anything but honest with her.
After four months she called me to say that she now had a boyfriend that wanted a serious relationship and we would definitely not be hooking up any more. I was fine with this. I was actually happy she found someone that wanted the same things as her. Then, about a month later in a conversation with a mutual friend, I discovered she had been seeing this guy for six weeks before she cut it off with me and had been in an official (fb official at that) for four weeks of that. Which meant not only had she continued to fuck me for the two weeks they were initially dating, but that she had continued to fuck me for at least three weeks into their official relationship.
I called her on it, she admitted it, I told her that either she told him or I would. Two weeks later I asked her if she had told him, she said no, so I shot him a message on facebook explaining the situation, and he thanked me for being a man and letting him know.
Cue her and her sisters starting to harass me. Threatening fb messages, threatening texts, threatening voice mails, and one of her sisters even bounced a glass off my head at the bar.
Why were they so pissed off?
A friend of hers saw the altercation at the bar and decided to fill me in: she had been having unprotected sex with this guy and wasn't on any form of birth control, but she told him she was on the pill. She found out she was pregnant about a week after this guy bounced her to the curb. I am so fucking thankful that I insisted on always using a condom, despite her saying she was on BC. She was trying to lock a husband down.
She actually contacted me via text a couple years later apologizing for everything and asking if we could get together sometime if I'm still single, so I changed cell numbers.
3) Again, ran into a former crush at a house party. I was 26 at the time, so this was almost a decade after having any interaction with her. Still sarcastic as all hell, still gorgeous. She started talking to me because she admired that earlier I had fought off a girl that was trying to take me into a bedroom by yelling, "NO! NO! I WANT TO PARTY WITH MY FRIENDS! NOOOO!" and ran out into the yard, then climbed a tree to get away when this other girl continued to chase me. Apparently she had never seen a single, straight guy turn down a sure thing with a hot girl just because they wanted to keep partying with their friends. I didn't bother telling her that the real reason I turned the other girl down was because I was on four hits of LSD and while I'm on LSD I find the human body revolting.
I said something off or reacted weird because she stopped and asked, "Are you also on acid?" So we spent the night chatting while sitting on the lawn, got her number after watching the sunrise together, then I turned into a giant wuss and didn't contact her for a month because I was so intimidated by her. She said that when I didn't contact her she decided to accept the invite to dinner she had gotten from a co-worker and that they were now dating. Kept talking, became friends, discovered as I got to know her that we would have never, ever worked out as a couple, so it really turned out for the best.
So ya, out of three crushes that I ran into years later I got:
1) Summer of great companionship, great sex, and a great friendship still going strong after five years.
2) Four months of amazing sex, huge amount of bullshit, giant disaster with some potentially ruined lives.
3) Good night of psychedelic conversation, new friendship.
Not too bad.