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 . . .