I just came back from my Caribbean cruise vacation.

A little background about me:

I'm a 26 y/o virgin, it's because I spent the last 5 years focused on start ups living in silicon valley at the cost of my social life. I lost all my friends, I didn't balance my life at all, until I got a huge wake up call when I was hospitalized for 3 months, I have Crohn's disease which is managed by life style but I was so focused on business that I neglected my health. While in hospital I decided I was missing out on life, and life isn't just work work work. When I got out I decided to take a Caribbean vacation, I deserved it!

I was recommended the book "The Game" by a fellow redditor and read it during the cruise. When I was 18 I went clubbing a lot and had grinded many girls and so I'm not afraid of touching girls, I'd have to be 18 all over again, like the days before I left to Silicon Valley. If anything I learned from business, it's how to talk to people, I'm excellent in interviews, and I'm really good schmoozing with people.

On the third last day of the cruise, I opened a hot cruise staff with a neg, that I didn't realize was a neg until I said it: "Were you at the club last night?", "No, I was working.", "Oh, because you look like this girl I saw at the club." We started fluffing and then I left because I had a dinner reservation. I didn't go back to her.

Girls throughout the vacation smiled at me, but I never had the balls to approach. I kept telling myself, I need to approach woman more, and I would walk up to a girl and then veer away. Until the last day, on the last day I kept thinking "fuck it, I'll never see anyone here again, if I don't sarge a few girls I'm going to regret it". I knew the feeling of regret would hurt more than the feeling of rejection.. so I hung around the pool.

As I looked at the pool on the ship, I saw many beautiful women, and I pondered which one should I go for. I saw a really chatty HB8 and thought: she likes to talk, so lets talk. She was laying on her elbows with her feet at the edge of the pool, and chatting with her chubby girl friend. I swam to her and did jealous girlfriend opener, this started an 8 minute conversation, and I didn't talk much, I just listened to her and made some jokes, she was from Florida. Every question she asked me I wouldn't give her a direct answer, but would either tell her to guess or a joke, until later on. She asked for my age, I told her to guess, and watched her and her friend talk about how old I looked for 5 minutes. She asked me what I did for a living, I told her "disposable lighter repairman" she didn't get it, and neither her friend, but didn't really care anyways. I did the ESP mind reading 1 to 10 test, I said 7 like in the book, but that wasn't her number, and neither her friends number. She replies "I'm too intelligent for your ESP", I laughed and she laughed too. We fluffed for another 30 minutes, and I learned everything about her. I never asked for her name, the book says never to introduce yourself, so eventually she asked for my name and we shook hands. I asked her was she was doing later, she told me she was going to the piano bar. She left to go to the bathroom, I left too. When I got back, 5 guys were chatting her.

Interesting, I thought if all the guys are going to go to that one girl, that leaves all the other girls alone. I saw a group of 5 girls, ranging from HB6 to 8, from Boston. I swam to them and did the exact same opener, with the exact same results, we chatted for 20 minutes, mid through I looked bored, and said "alright I'm going to go swim around" and then they started asking me more questions trying to refuel the conversation (IOI?). I kept in mind about what the book said about validation, and made sure that I was validating them rather than they validating me. I asked them what they were doing later, they said they were going to the casino, I said "you're going to lose all your money", which led them to start talking about which games make the most money, and probability. It's interesting how I never had to talk much, I would just say one liners, watch them chat back in forth about what that topic. I told them what I did in silicon valley, they kept complimenting me. They said they were going to go eat and left.

It seemed after those two sets, my fear of approaching eliminated. I walked around and a saw an HB8 that I've been eyeing throughout the vacation, earlier in the vacation she walked by me and I half smiled at her, she passed by me looking stuck up. The next day the same thing happened, except I didn't smile at her, and I looked stuck up, she also had her stuck up face on, although right when we passed each other, she had this really sad expression like I rejected her. Fast forward to the last day of the cruise near the pool, she's half asleep on a pool chair. I sit on a chair one over from her, as to not look creepy. I say the jealous girlfriend opener, she wakes up "huh? what was that?", I say it again, and she starts saying the same thing the last two sets did. Eventually she says a word that doesn't sound American, I'm from Toronto, and everything about this girl sounds Toronto. So I interrupt her and say "wait, you sound like you're from Toronto, are you from Toronto?". In the next 5 minutes, I guess EVERYTHING about her, age, the university she goes to, the suburb she lives in, the ethnicity. She was impressed. Without even asking, she tells me where she works (IOI?), I tell her I live 5 minutes from there, she says I should come by (IOI). I tell her it's dinner time soon and I gotta get going, she tells me come to her workplace, I tell her "I'll just see you around ship" sounding not so interested, she tells me she's going to be at the club at midnight. I say "but wait, I didn't get your name", she makes an "OHHH" sound like she totally forgot to introduce herself. She gives me a really strong handshake (IOI), I say "that's a strong handshake!" as I get up and start walking away, she says "that's the only thing I learned in business class", I reply as I walked away pointing at her with a wink and a smile "business class, now that's a good investment!". I don't think she got the pun.

Come midnight, I walked to the club, its completely dead inside, and no one is there. So I said I'd go to the piano bar and see if the girl #1 was there, she was there with 5 other guys, I don't think I was ready to deal with 5 guys and 1 girl. So I went to the casino, and walked around, I saw the staff chick I sarged earlier, but didn't say anything because she was dealing a table and didn't want to get kicked out.

A half an hour later, I walked by the club and I see girl #3 with 4 guys. Fuck, again with the guys, I start walking away, and then think "fuck it, I don't care what happens", I turn around and enter the club. I approach her in a half-dancing/half-walking style. She says "oh its you!" and leaves the other guys to greet me. She's half-dancing, I'm half-dancing, other guys keep coming up to her. I just sit down on the bar stool and not doing anything, and just watching her talk to all these people. She walks by me a few times lip syncing, half-dancing and pointing at me. I sit and watch. Then these guys ask me to take pics of them with her. I start taking them, but when I get to the third camera I give it back to them and say "This shit isn't free, you're going to have to pay me.", they start begging and I shake my head like "fine whatever" I take the pics. I sit there watching in my seat, for another 10 minutes. I see this colombian chick walking near me, I start talking to her, but she can't speak English, so I speak to her in broken Spanish. What the heck, I got nothing to lose. Hey boyfriend comes and takes her away. I start talking to her boyfriend, he's from Peurto Rico, he does this elbow props with another guy, so I get in there and do an elbow props with him. It's cheesy as hell, but what the heck I'll do it, as Mystery says "own the guys, own the women."

After another 10 minutes of watching, I get up, walk through the circle of guys surrounding the girl I met at the pool, and say "I'm leaving", she gets really close to me, I put my hand around her hip. She asks why, I tell her I gotta get up early tomorrow, she says "Just stay up all night, don't go to sleep, I'm going to be up all night until tomorrow, do it" I say "You're crazy, besides I got a plane to catch" so as I start walking away she says "Wait, whats your number, do you have a business card or something". I shake my head, and pull out my iPhone and give it to her. She puts in her email address and full name. She says "Come to [workplace name], alright? come, come, come to my [workplace name]", I nod and she takes my hand and gives me this weird upside down handshake/slide thing. I say "I'll only come under one condition", "what's that?", "you gotta dress me" (I don't know why I said this, sounds lame), she replies "i'll dress you! come", I exit the club.

I added her to facebook, I know, big mistake, I just read the FAQ. So instead I cleaned up my facebook profile and removed all the useless pics and info, like the advice said to do. She hasn't arrived to Toronto yet, she'll be in either tomorrow or the next day. After thinking about this experience, I thought maybe I should have stayed with her all night, and then said something like "listen I'm leaving the club, tell your friends you'll be back in 10 minutes and come outside" and then should of taken her somewhere dark and do the picture routine escalating to the make-out.

Should I go to her work place? I'm thinking saying something like "I don't want to go to workplace that sounds boring, what time do you get off work?"

Critiques and advice much appreciated!