Her #4

So . . . this is a strange one. I wouldn't have counted it, but that thing 2 told me that I could. Whilst in my old home town on business, I had drinks with EW of EEB. So . . . whilst with EEB, I heard stories . . . you know . . . the types of stories that you hear from a current of an ex. So, it turns out that we have a TREMENDOUS amount in common . . . we both have a background in performance, love to cook, lived in the same 2 cities, and . . . work for the same parent company. Within my job, it is imperative that I know all of the players in all of the brands . . . so knowing her is important. Even more than that . . . she is amazing. It's funny . . . we all see different parts of one another when in relationships, so it's interesting to look from another angle . . . but she is incredible. My regret for her? I don't think that at the time that she was married to him that she was as confident as I am (a fault as that may be) and I can't even begin to imagine what she felt during the course of this relationship. She is at an amazing place in her life, and realizes that all things prior lead to where she is right now. And she knows what I've dealt with . . .

Anyway . . . why can it be a "date?" Well . . . it will probably lead to a more "real" relationship than any other that I have been/may go on . . . plus . . . we are colleagues once removed. I owe a lot to the short time that I have spent with her, and wish to her only the best things in love, life and happiness. It is very strange when you come to the realization of why the "gods" throw certain things at you . . . was it the something that you originally encountered? Or that with which you gained through the original encounter?

So the date? We didn't even talk EEB. We talked work, each of our lives at the moment, our respective cities, our past lives, and how we will be intertwined via work. Left it KNOWING for a fact that I will see her again ;) Best date yet? Mayhaps.

Her #3

I relegate #3 to a weekday night. This is partially due to my schedule (I love it when guys start off by saying, "I love that you're so busy" which quickly turns to "you never have time for me" or "your job is a convenient excuse" . . . but I digress), and partially due to the fact that there are less expectations from the other party. Additionally, #3 is also GU, and this complicates the matter.
We meet at a restaurant downtown. I have been hesitant to tell any of my friends that I am going on this date b/c he is a friend of FTF EEB . . . and what gets back to her gets back to him, and the passive/aggressive texts ensue. I wait at the bar for him (after walking down one of the nastiest streets in the city, where a transvestite complimented my shoes ;)) and order a glass of wine. Wine=corked. So, I do a thing that I have ALWAYS wanted to do, but never have . . . sent it back. I am finally educated enough on wine that I can tell that it is bad, and not just cheap. Cheers for me!
#3 eventually arrives, and is wearing pleated front pants. Oye! That has just ensured that I will never look below the waist on him again. We have a few small plates at the bar and continue to down wine (when in doubt, keep drinking). Special props to #3, who bravely ate the appetizers that I chose, 1 which had squid ink, the other which had full sardines with bones and heads. We get to our table, order dinner, more wine, and more talk. He is nice. VERY nice. Just not my type. I see him text FTF EEB, and realize that she now knows that we are out. We agree to meet her and her new man at a regular watering hole. Head up that way, a couple of drinks later, I have him drop me off.
Nice . . . average . . . will hang again as friends, zero spark. Tis ok. Better than the one that openly told me that I intimidated him at least a little . . . but he is pre-experiment, so I won't expand. ***Note to any guys out there reading this . . . You may say this to a woman thinking it's a compliment. Most likely a woman who intimidates you knows that she is intimidating, and this only make you look like a pussy***

Her #2

So there are moments in dating when you don't understand why someone has asked you out, as they clearly don't really know you, but . . . for the benefit of my readers (as well as to prove a point to my bro) I agree to a date with bachelor #2. He is GU, which has made setting a date a challenge, but we work it out for a Sunday evening. This happened to be the final night of a Yankees/Red Sox series, and as yours truly worships the house that Babe Ruth built, I had to get the game in before dinner. I suggested we meet somewhere to watch the game and then head to dinner. As #2 is GU, he does not know my city . . . but decides to recommend a bar at which to watch the game, and defer to my choice of restaurant (we will both live to regret this). #2 suggests a place near my place. Great, right? Ummmm . . . no. He suggests the absolutely douchy-est bar that exists in this city. Think 22 year olds, LOUD bad music, and, oh yes, beer pong. This should be amusing.
As happens in this great city, Sunday Funday is a drinkfest that often involves bar crawls done in costumes, etc. #2 sends me a text letting me know to "look for the old person at the bar". Shocking. I enter, and said bar (to which I had formerly prided myself on having never entered) is everything that I had dreamed it would be. Music BLARING, drunk post sorority/fraternity crowd (many of whom are in costume) in various stages of dancing, stumbling, etc, and a ROUSING game of flip cup and beer pong in the back. Ick. Mercifully, #2 has gotten 2 seats at the bar right near the TV. CC's pitching, Yanks are winning, small talk ensues. I see a girl with a Red Sox hat on and boo her. She doesn't get it. I try to explain . . . she still doesn't get it. She goes to play flip cup. REALLY drunk couple is dirty dancing behind me. Girl standing next to me at the bar keeps leaning into me. Pocahantas is also there. Oi. Someone comes to ask us if we want to play beer pong. I haven't read the article about how it is increasing the spread of mono and herpes, but I can assure you that if I am ever going to play, it will NOT be here. I continue sipping my sweet tea vodka and lemonade (it's the new black, after all!) and text my brother to try and make our dates meet up. We end up deciding against, but it perhaps we could've introduced our dates to one another.
We leave as Mariano is taking the mound (the Yankees are well in the lead, yet the closer is sent in. You NEVER pitch your closer in a non-save situation. My diagnosis? Bad management) and head to dinner. #2 drives.
We arrive, and there are only seats at the bar. I'm up for it. I'd been to the sister restaurant of this one, and was really eager to try (please note that whether or not I have a good date, I am determined to have a good meal). Food starts arriving, and we start nibbling. #2 begins to sop his brow with the napkin. Ummmm . . . I don't THINK it's hot in here . . . do I apologize? Offer to move? I let it go, and make sure the ice water keeps coming. This is not working. I finally mention that it is hot in there, and apologize, to which he explains to me that he sweats from spicy food. Ummm . . . you think he would've shared this with me when I asked "Is there anything that you can't/don't like to eat?" Never mind. When he went to the restroom to do a final wipedown, I paid the bill and readied myself to head out.
Look . . . he was nice . . . but we didn't click. No worse off for a Sunday night . . .
NEXT?

How I met #2 and #3

So this is about first dates, right? "You only have to like them enough to be able to sit through one date with them." This is what I tell my brother. So . . . I took a chance on this one.
I had met bachelor #2 (SMM) at a birthday pary for three different people that was held at a regular wattering hole a few weeks back. He showed up very late in the evening, and as I was the only moderately sober one, he seemed to find me appealing . . . I think I was just the only one who could compose a string of words greater than 2, and therefore I won. Whatever. So let me digress for a moment and explain that I almost did not stay at this party for more than 10 minutes. About an hour prior to the party, EEB called me back after abruptly hanging up on my only to explain that he thinks that we should try and just be friends. As I know EEB quite well, I knew that this meant one thing . . . that he had found someone else. When we arrived at the party, he let me know that he felt so great! Great. I wanted to cry, especially as he immediately explained this to FTF EEB. Were the gods all against me??
Anyway, I pulled it together and ended up having a good time, and expanding my circle out of the incestuous one that would invariably continue to break my heart. Had one unbearably drunk guy talking to me throughout the evening, but struck up conversation with a more sober one (later to be known as bachelor #3). As luck would have it, bachelors #2 and #3 sort of know each other, and not only that, but happen to both be friends with FTF EEB. Grrrr. Oh well! Just one date . . . just one date . . .

Her #1

After a Friday night dinner with the ex in which I proceeded to get yelled at the entire time (yes, this is now restaurant #2 in which I can never again show my face, in fear of humiliation when the owner and waitstaff who heard the entire thing invariably recognize me -- oh . . . and this one is in my neighborhood. At least the last one was mercifully across town) I embarked on date #1, also known as the "non-date date." What is a "non-date date", you may ask? In said scenario, I am going out with the brother of a friend, with whom I've hung out numerous times, and who at one point said, "I have to take you to dinner one time." Is it a date? Is it not? I don't know . . . but I figure it's good enough to count for a "first date".
Bachelor #1 arrives at my apartment a few minutes after 8. I ask him if he wants to head straight out or come in for a drink first. Don't really remember who finally called it, but tequila tasting at my place it was. Don't judge. It wasn't the tequila tasting that you did in college. We're talking $200 bottles . . . 2 glasses each, drink like scotch. By the time we chatted over tequila, it was nearly 2 hours later, and we had to head out in fear that restaurants wouldn't be cooking after 10 (God, I miss NYC!).
We ended up heading to the restaurant on my corner, to which I've never been, despite the fact that I have lived there for a year. GREAT meal, great conversation, great wine . . . what's not to love? Not sure how it happens, but we decide to stay out. As we're searching for a next destination, I pull him (willingly) into a bar that has pop-a-shot (a friend of mine and I later decided that this will be our euphemism for sleeping with a guy . . . "did you hook up? . . . We ended the night playing pop-a-shot"). After being utterly destroyed by the db's already playing, #1 recommended a game of pool . . . with which we ran the table until the bar closed :) Never realized that my secret pool skills would ensure that my date could last longer.
All in all . . . one of the best dates I've had in a LONG time. Wasn't in anything that we did, just the vibe. But alas, this is an effort in first dates, so there can not be a second (unless I sneak it in there somewhere . . . )
Cheers to you, bachelor #1, for a brilliant start to this experiment!

The Challenge Begins

Two single siblings, one great city, one common goal -- 25 first dates each . . . no repeats.

How to find these dates? It's up to each of the genetically connected duo to find their own . . . and they can only go on one date with each. The mission? To make sure you spread your eggs into MANY baskets instead of putting them all into one.

And so it begins . . .