There are some artists who have such a great repertoire of songs that it’s impossible to pick their absolute best. If you had to pick just one song of some of the greats that we grew up, like say Madonna, could you? Evidently, City Winery couldn’t when it held its Madonna wine pairing of 30 songs, 30 wines.

In anticipation of the event people speculated what wines would be paired up with “Like a Virgin,” “Like a Prayer,” and “Justify My Love.” I suspected “Like a Virgin” would be a young never before touched beaujolais nouveau (even though it’s out of season), “Like a Prayer,” a Bordeaux from Saint Emillon, and “Justify My Love,” perhaps a White Zinfandel because it’s a wine people need to justify their love for. The only notable “wine”of the three songs, was the non-alcoholic “City Winery Kid’s Sauvignon Blanc” that City Winery chose for “Like a Virgin,” to which I have two comments a) why bother giving us a fake wine and b) are they actively encouraging kids to drink wine? That better appear as apple juice on the menu when bambinos are allowed in!

The event started when we heard a man off stage singing the lyrics to “Holiday.” We thought we might be treated to a female impersonator, but no such luck (although later we did see a famous drag Queen who has appeared on Project Runway named Acid Betty). However, our MC did not disappoint. He even came armed with a Geisha like fan which he used to fan himself. That man had some serious sexy Geisha fan moves. Note to self, buy a Geisha fan.

BTW, I have solidified myself as a hag as it was easier for me to get more numbers from gay men than it is for a dog to pick up fleas. I was honored when I was invited to come with them on their next adventure, but since it was straight love I was looking for, I politely declined.

I took notes during the different flights. I can read the earlier ones and I will admit on the second half of the sheet, I am unable to decipher the babble. The legible notes next to the corresponding number of wines are as follows:

3. La Isla Bonita = Sauvingon Blanc: “Are they seriously serving a white wine with a passionate song like this? I picture a fiery passionate red.”

4. Material Girl = Rose: “We are starting to do the camp fire sing along at this point and the line ‘Boys may come and boys may go and that’s all right you see’ was sung at a particularly high volume in unison.”

8. Papa Don’t Preach = a white wine I’ve never heard of, but I evidently liked because I starred it on the wine list: We are starting to sing while we toast at this point. We debated whether this was the video where Madonna wore the “Italians do it better” t-shirt. It was. I remembered it because when I was like 8 and I watched it on Friday Night Videos (we didn’t have cable), I thought it was a cool shirt. I wasn’t sure what “it” was, but it made me want to be Italian. I also laughed as I now recognized that she and her “baby” were riding the Staten Island Ferry on a date. Obviously Madge was slumming it in her pre-living in a material world days.

10. Rain = Muscadet: Our MC dramatically announced that rain was a metaphor for tears. I thought he was going to go deeper with this analysis to introduce the Muscadet, but he didn’t. Bummer.

12. Ray of Light = some random white wine: Me to a friend, “This tastes dry, does it taste dry to you?” My friend, “I think it’s as fruity as this whole room.” Clearly, my palate is having an off day.

A discussion ensues over why City Winery was only able to obtain 18 of the 30 videos (IP issues or availability-my friends in the music industry swear it’s b/c of IP issues, I take their word for it). So instead of 30 videos there is a “Moments of Madgeness” compilation of videos for the other 12 songs.

16. Borderline = we have now switched to red wine: “I wrote fashion glasses?” At first I have no idea what this means, but now I remember we were trying to figure out if our hipster and pseudo-pushy waiter’s glasses were fashion glasses or real glasses. Consensus, fashion glasses.

18. Express Yourself = Barbaresco: At this point we’re in FULL girl power mode as we all belted out as our toast, “DON’T GO FOR SECOND BEST BABY.” The rest of my note on this point is indecipherable.

22. Justify My Love = some red italian wine: MC sings “I want to kiss you in Paris, I want to hold your hand in Rome” and then he says “this wine makes me think of an Italian boy…it tastes like an Italian boy, it smells like an Italian boy and who doesn’t love Italian boys.” I must LOVE Italian boys as I starred this one.

23. Don’t Cry for Me Argentina = Malbec, obvi: Dear God, I’m not sure if it was my love for Argentina or Malbec or what, but I am now signing full blast “DON’T CRY FOR ME ARGENTINA, THE TRUTH IS I NEVER LEFT YOU, ALL THOUGH MY WILD DAYS, MY MAD EXISTENCE, I KEPT MY PROMISE,” while raising my glass to the MC who is acting very Evitaesque while Geisha fanning himself and looking at me and loving the Evita like adoration.

26. Beautiful Strangers = another new red wine: Disclaimer as my scratch paper has been highjacked because I’m on the dance floor at this point. The note says, “Madison is dancing with beautiful gay strangers.”

The rest of the night involved me getting called up to stage because it was my birthday at which point the MC spanked me with the microphone. Weird, but first official birthday spank. Next year, I’m asking for the Geisha fan.

There are days that make me love New York, and then there are days that make me LOVE New York. This past Saturday ranked as one of my top 5 all time favorite days in New York. The day was a bit touch go in the morning as a certain someone had only managed to catch about two hours of sleep from the prior night. The day was an extension of “birthday week,” which is my excuse to do one new thing a day every day of the week of my birthday. Basically, it’s my motivation to put the Netflix away, get off my tushy and explore all that New York has to offer. This year during the actual week of the big, ahem, “27,” (being 29 is so cliche so I’ve decided I’m going younger every year) I was too swamped to follow through so I made a deal with myself to do five new things in the month of August. Now, mind you I didn’t plan to do them all in one day, but I nearly accomplished my birthday week bucket list in one day.

We started the day off by taking advantage of the Summer Street Program, which Bloombie (that’s my nickname for our billionaire Mayor) introduced last year. For three Saturdays every August from 7 a.m. to 1 p.m. streets are closed off from traffic from the Brooklyn Bridge to Central Park. There are free bike and skate rentals along the route. My friend and I “rented” bikes and hit the open road and by open road I mean Park Avenue. A Park Avenue without any cars sort of gave it the I Am Legend and Vanilla Sky feeling (you know where Will Smith is driving around Park Avenue without any other cars on the road and Tom Cruise is running through a very empty Times Square). I feel like I should have a theme song for this portion of the day (Will and Tom would).

From there we headed to the upscale portion of the day and went for High Tea at Lady Mendl’s. Lady Mendl’s has a very French chic vibe. I am not going to lie, the favorite part of High Tea was seeing a sugar cube topped with a little pink flower on it. Oh so pretty and girlie! I secretly pretended that I was living at Lady Mendl’s and that we were in my salon and I was expecting various literary giant who all seemed to live in Paris at one time or the other circa the 1920 and 30s. Whatever big girls can play house too!

We then attempted to go to Pier 40 to do some free kayaking on the Hudson, but accidentally ended up in Brooklyn. The A train was on a covert black ops mission and jumped to the F track and next thing we know we’re in Brooklyn and we had to wait at a stifling hot train station. This would not deter us on our goal. Rather, it made the breeze off the Hudson that much more enjoyable when we finally made it to the pier.

Kayaking on the Hudson isn’t for everyone. First, you must be resolved that you’re not going to think about the fact that you will get soaking wet from the gross Hudson River. Second, you must forgo your fear of capsizing and/or accidentally falling out of the boat while trying to get into it (I actually thought I was going to miss the boat entirely and go head first into the Hudson). Third, you must be able to not freak out every time it appears like you’re going to have a head-on collision with inexperienced kayakers who have no navigational skills. There should be a boating test that people have to pass before they’re given an oar! The water was choppier than I expected and I couldn’t look at the boats that were anchored in the water since they were rocking side to side more than Elvis did on the Ed Sullivan show (not a good thing to look at if you’ve had a few too many the night before). P.S. there are changing rooms and a locker area on location, but word to the wise-if you bring a change of clothes don’t forget the most important thing, i.e., back up underwear because you will then be forced to choose which is the lesser of two evils. I’m just saying.

After our little Christopher Columbus sailing of the high seas expedition, we went for a walk up the West Side Highway and over to the High Line. For those who haven’t checked it out, it’s a must see as it is an example of urban planning at its finest. Believe it or not, we had intended to hit a few small museums, but thanks to our unexpected No Sleep Til Brooklyn detour we ran out of time. So, instead we headed to Chelsea Brewing Company for a free tour, which I highly recommend. Our beer sommelier was generous with the three pitcher pours of Checker Cab Blonde, Sunset Red Ale (my favorite), and a Stout beer the name of which escapes me. You also get discount beer tickets for pints at the bar. I wonder if anyone gets banned from coming back too many times. It was a motley crew on the tour though as I think we may have had a mail order bride and someone with daddy issues (seriously my friend and I couldn’t figure out if this girl was with her father or her boyfriend-it was ambiguously creepy).

We finally ended the evening at The Frying Pan and had a sunset cocktail of white sangria (a bit reminiscent of peach wine coolers) and garlic fries (evidently they’re famous for them). We could have stayed longer, however, I had dinner plans to meet a friend from out of town so where did I head to meet her? The Shake Shack because why not end the day with another New York institution!