Had a funny story from last night I thought you guys might enjoy and was curious to hear your thoughts...

So last night I went on a Grouper date with two of my buddies. For those of you who may be unfamiliar with this service, Grouper is this site where you link it to your Facebook, you answer a few questions and they have an in-house person who matches you with a girl who they think you'll go well with. The wrinkle is that each of you brings two friends so it's a 3 on 3 blind date. Neither of you know who the other is or what they look like - they just tell you when and where to meet, have a bunch of bars and lounges that they work with. Each person puts down $20 to ensure they show up and that covers the first round of drinks. Pretty decent service; I've gone on one before that went fairly well.

Ok, so last night I go with my roommate who has been bugging me to do this for months and another friend. Both of them are kinda on the quiet side so I'm definitely the most outgoing of the group. We meet the girls and have drinks, order a bunch of appetizers (oysters, sliders, etc) and just chat. Everything goes pretty smoothly and after a while we're ordering Patron Cafe shots and ribbing the waitress when she comes over. So we're just chatting about random stuff and I catch that one of the girls (IMO the best looking one) has been kinda stealing glances here and there. Couldn't tell if she was doing that to my friends as well but I took it as an IOI. Anyways, somehow it comes up that they like going to strip clubs and did it with a group of guys a month or two back. Well, one of my buddies loves that kinda thing so we ask the waitress for the check and decide to go to this burlesque place around the corner that one of the girls knows. We tell the waitress what we're doing and she tells us that she might meet us there which was just hilarious. The girls go to the bathroom and while they're there I go up to the waitress and get her #, telling her I'll text her and she can meet us after her shift. Didn't really care about meeting up with her but did it moreso because when we left, predictably, one of the girls (actually the one I liked, luckily), says "we forgot to get that waitress' info!" to which I responded that I had already taken care of it and pulled her # out of my pocket. Pretty solid move if I may say so myself. We go to the burlesque place, I order drinks for everyone and we're sitting at a table in the back, all talking but me and her are also having a private convo on the side. I tell her that I have Rangers season tickets during one of my stories about hockey and she tells me she's never been to a game. I tell her I may have an extra seat to a game this week and get her #. So far, everythings going pretty well - later, separate her from the group, teach her how to make a rose out of a napkin at the bar (DHV), etc. So we end up leaving around 12:30 and we split a cab; my friend and I planning on getting out at our place, paying the fare and having them go on their way at a reduced rate. So, we're about halfway there, I'm in the passenger seat while my friends in the back with the two girls. The night was kinda hazy at this point but somehow the girl decides to dare me to take my pants off in the cab. No way am I about to be shown up by this girl so after the driver makes it clear he doesn't care (awesome cabbie), I take my jeans off. I tell the girl that its going to be a very cold walk for me to my front door (it's about 15 degrees in NYC at this point) and she should give me her pants. To my surprise, she actually takes her pants off and we make the trade. I get out of the cab, put her pants on, she gets out to give me a hug and I head home past a very confused doorman to my apartment. Woke up in the morning missing my favorite pair of jeans and with her pants on my dresser.

So, that's about it - pretty successful for a blind date I'd say. Texted her a picture of me in her pants last night and she responded that she and her frined were using my pants for pajamas and they were super comfortable. I've got a time bridge to Tuesday when we're supposed to go to the Ranger game at Madison Square Garden (waiting for Sunday to confirm it). I have to think that trading pants was a big IOI - even if it was a spur of the moment dare, if she was disinterested I'd assume she would not have given me hers but would have just kept mine. Would also assume there's less a chance of flaking since it's a specific time bridge and she (intentionally or unintentionally) did a reverse-leave-behind and we have to make the exchange (unless she just wants to steal my jeans). Looking forward to seeing how this goes; I think I'm in pretty good shape here but could be wrong. In any case, here's to hoping that the next time my pants come off for her it's under more traditional circumstances

Congrats,you are a winner Yeah it was an IOI,and now you have something of hers,and she has something that belongs to you,so seeing each other will happen for sure.That girl is surely interested in you,all the best !!!

So went out with the girl yesterday. It went pretty well - met up at a bar before for a drink and then walked up to MSG. She had never been to a hockey game before so there was a lot of explaining on my part and some kino when leading her through the arena. Even let her borrow my Rick Nash shirt though I told her she wasn't allowed to steal that one. Anyways, though I asked her to bring my pants back I didn't bring hers, saying she never asked me to bring them. In reality that was my plausible deniability to head back to my place after the game. So after the game we came back, exchanged pants and then I suggested we have some champagne on the roof. Our building is 44 stories with 360 degree views of NYC so we went up there and had some champagne. It had recently snowed so part of the roof had a couple inches of snow and somehow we got on the topic of her taking self-defense classes. I told her I used to do judo and she asked me to teach her some moves. Anyone who's done any judo throws knows many of them end with you on top of the person so naturally I half-did them first to calibrate, then I asked if she wanted to see them at full speed and she said yeah so I tossed her (made sure to have her land gently of course) and then k-closed from there. It broke a personal rule of mine to never k-close on a first date but I justified it to myself because we did go on a group date beforehand, plus I just really wanted to. Anyways, I walked her to the ferry and kissed her goodnight, then sent her a teasing text afterwards.

Seems like a perfect evening, and in some ways it did go exactly as I had hoped but there is one thing that's kind of confusing me. When we were together Thursday the vibe was really great. Then, when I was texting her in between she was very different from most girls that I text with (granted, New York Jewish girls are abnormally into texting but whatever). Weird response time, not a lot of excitement and kind of blah attitude overall. So much so that I despite all the IOIs from Thursday I half expected her to flake but she came and it seemed like everything went perfect. However, texted her something half teasing but telling her to get home safe last night, she texted me something funny back, I texted her something funny...and no response. My current notion is to wait for her to text me, but she is also leaving for a weeklong trip to the Carribbean on Saturday. Debating if it's worth sending a text or better to play the waiting game and gauge interest, or if I'm just reading into this way too much and she's just a bad texter. What do you guys think? I've analyzed it and feel like I've played it pretty well so far but for some reason just not getting the between-dates response I'm accustomed to.

Text her once she is back,not before...Initiate by asking if she had a good time there,etc

Then if you have a good convo going,ask her out again,if she is still weird,freeze her out

never text a girl asking for re-assurances, thats Beta as fuck

I meant a good time in her vacation time,not at his place.Thats why I wrote that he should message her when he is back.

Thanks for the input guys. I was going back and forth all week and ended up texting her Friday afternoon. Also i did decide to text that girl. I felt like I had gotten a good enough vibe that the risk wouldn't be too great. Figured the small risk of losing the freezeout was worth the potential benefits of giving her a small assignment during the trip.

She loves to do pickle-back shots so during my lunch break I specifically went to the supermarket and took a picture of a jar of pickles and texted her with the caption "want me to pick you up a jar?" The goal was some callback humor and making it seem spontaneous since it would seem like i just happened to be in the supermarket and thought of her. Exchange below (my comments in italics; also, while the whole convo was over the course of several hours, any consecutive texts were sent at the same time):

Me: Want me to pick you up a jar?
Her: Image didn't open , but i'm assuming it's pickle juice??? If so, hellz yeaa!
Me: If that image really didn't open you are one of the finest guessers I have ever encountered haha. All packed up and ready to go?
Me: Or did you decide to cancel the trip and watch Olympic hockey all week
Her: Hahaha you got me Adam..
Her: I'll spend my week practicing the goal song (at Madison Square Garden there's a song that's played everytime the Rangers score - I teased her for not singing along when we went)
Me: Judo too! Haha also one of my colleagues just gave me free tix to see phantom again this week so exciteddd
Me: But yes learn the goal song and let's def go to another win when you get back (impossible since NHL is on three week break for Winter Olympics but figured it was a good way to make preliminary plans)
Me: Oh and don't bring knives on the plane - TSA is not going to like that (when we were waiting in the security line at Madison Square Garden she joked that her bag was full of knives and guns)
Her: Haha, fine will leave the knives at home.. Sounds good, lets touch base when i get back. Have a fun week!
Me: You too! Get a nice tan and bring me back some souvenirs
Her: Will do


The whole point of the exchange was some callback humor and seeing if she'll actually follow through on bringing me back a souvenir. If she comes back with nothing but still wants to hang out, clearly I have some work to do. If she comes back with anything (i.e. keychain, t-shirt, etc) then I think it's a fairly big IOI and I can proceed with that knowledge.