From My Inbox: How To Entertain A Lady In NYC This Weekend

Last October, you guys helped us find a date for this guy. Gerry (left) had just moved to NYC from Scranton and with a PhD, a high salary gig, and an athletic frame, he made us wonder  why the heck we would help him find a date. Alas, Gerry checked in with me today on email. And! He has more questions! Below, his email, my answers in italics.

Gerry's Email:

"As a woman of class, style and glamour, and the "IT" person of knowing what is what. I am turning to you for advice."

Okay, first, stop flattering me ;) Also, this reminds me of that amazing Rolling Stones Song.

I'll be in NYC entertaining a lovely lady this coming THURS FRI SAT Jan 20 to 23. I would like some of your suggestions as to where we could go out at night and how to keep her entertained?

If you can figure out how to keep any human entertained for that long, you should be the one writing this response, not me. That being said, happy to see you with a lovely lady and not a dead fish.

Thurs night Dinner ? Mari Vanna - a Russian restaurant 41 East 20th Street, New York, NY?

Hmmm... I have never heard of that place, but genuinely I, (and I realize this sounds snobby-it's not meant to...it's just the truth), tend to stay below the double digit streets. I think, hands down, the best place to start the weekend is Il Buco. I went last night and tend to hit it up at least twice a month. It is a romantic, quintessential NYC spot that just gets everything right. Here's some inside info to use on your date: the restaurant used to be an old antique store, and the man responsible for its transformation (the current owner's ex Italian lover) was such a pure foodie that he believed  that it was not only about a "tomato wanting to be a tomato" philosophy, but it even starts with the WATER. He made sure the restaurant started with getting the best water, salt, and olive oil that were physically available to them. The result is inspiring, and his touches have managed to stick around 20+ years later.

Bar? I was thinking Brass monkey, meatpacking - casual attire

I would head from Il Buco to the Bowery Hotel for a drink (but I'm biased). It's right across the street which is nice, and it will have a cool scene going on on a Thursday which will take the pressure off of you guys.

Friday night Dinner ? Bar? She likes semi formal events. Perhaps a upper class club where i can wear a suit and she a dress. She loves to dress up.  What about The top of the Standard Hotel in Meatpacking? (Boom Boom Room?). Impossible to get in, correct?

I am the worst at Friday night plan-age. We tend to hit the movies and hit the hay early with Charlie Rose on dvr (sexy right?) Now Gerry, I get that she likes to dress up, but I would save that for the next night. Friday is the night to really get to know each other and just hang out. Plus it's not a big night for people to get in cocktail attire (at least from my experience).  Because she's coming from Toronto, and because I understand the importance of getting the "New York" experience, I'm going to tell you what I think you should do. Please note (before my office continues to make fun of these choices), this is not a necessarily a night recommended for people LIVING here. O.K. here goes:

Take her to a speakeasy OR PDT (the "secret bar" in the East Village). Or this place that's getting buzz: Barramundi.Milk & Honey, Angels Share, Little Branch, are also all decent drink spots. If it wasn't so cold out, I would have you take her to 230 5th and get a drink on the roof. It is really cheesy but a great great view. You should do this during the day, now that I think about it.  Then go somewhere really neat for dinner like Freeman's - the restaurant in the alley, or the basement of La Esquina - a restaurant  where you have to walk through the kitchen in order to get to your seat. As an expert of taking out of towners to dinner, both are big hits esp for young people.

As for after dinner, I am having trouble with where to send you. The GofG office isn't much help. Answers have ranged from the Standard Beer Garden, to some wine bar in the West Village I haven't heard of, to "Brooklyn is the only place I know." So there you go. Honestly, I would head to the Jane Ballroom and call it a night. Again, I'm a bit biased. It's probably a bit crowded and the door will be tough, but it is where I would go, should I actually have to head out after midnight on a Friday night in the city.

Saturday night Dinner? Bar - ? 1OAK? or Hotel Gansovert on Park Ave?

For dinner, you guys should do your dress up night, but skip the cheesy social clubs uptown. Or go, I just really have no idea where or what would be remotely up your alley as I don't do these kind of things. My friend John Munson may know; you could send him a message on his facebook. Otherwise take her to ...

Raoul's -this is a no brainer. Classic. Can't go wrong. Homerun.  If you can't get table, head to Blue Ribbon around the corner (though you should just try and make a reservation at Raoul's earlier this week-shouldn't be a problem. Both places are in my top 10 and both are really important to experience at some time in your life. If you are in a complete bind and can't get a table at either the day of, head to Omen around the corner. It's pretty good and always has spots. I would tell you some cool places I've been to like Dellanima and the like, but the chances of getting a table on a Saturday night are slim. Giorgione's is also a great bet (and owned by the guy that started Dean & Deluca).

After dinner. Now, another thing you should know about me, I hate nightclubs and always have. I shouldn't say "hate," because sometimes I actually like going to them to watch people and sometimes I have enjoyed dancing on occasion. However, don't let my job title fool you, I really am not the right person to talk to on the matter. 1Oak, Avenue, Lavo, all seem like good bets if that's your thing. I think the Jane and Boom Boom Room are the top two places to go if you are dressed up on a Saturday, but this is from a very limited view point and shouldn't be taken as a guide.  Also, the doors are hard to penetrate. Sorry I can't be of more help with this, hopefully someone on GofG is reading this and can get back to you with more substantial advice. Oh. The Box? That is always shocking for people (and quite a fun experience).

Day time --Central park --Shopping --Rockefeller center (skating) --Grand Central Terminal --metropolitan museum of art --American Museum of Natural History? --Where are the shopping centers?

All of these sound fine. I tend to, in general, try and stay away from people that look like they are from out of town, but you def should hit up some New York famous spots. As far as "shopping centers," I'm not sure what you mean by that. Head to Soho, Nolita, 5th avenue, oh I don't know really. I love Scoop stores, and I really also love just walking around the West Village, but shopping is never a high priority of mine when I'm traveling to new places.  Take her to Balthazar for brunch, go hear the pianist at Bemelmans Bar at the Carlyle. Get a burger at Shake Shack, check out the new Eataly, walk the Highline, go to the New Museum, take a cheese class at Murray's, have a coffee at Dean & Delucas. Take her to the Magnolia Bakery in the West Village and go print a book at McSweeney's bookstore. I mean. It's NYC, and I really would just walk around experiencing it. That or get out a lonely planet guidebook.

By the way a lot of people FBed me because of that bit on your gossip column / blog. But all lived elsewhere but NYC! And they were like "wow if you only in Birmingham AL..or if you were only in Chicago...So nothing really came of it.This girl I'm hanging out with is From Toronto, and I met her NYE in Montreal (where i am from), so we'll see...

Gawd. people can really be lame, can't they? I mean, it's hard enough trying to meet your someone through the internet, to think that it could happen from another city?! Anyway, glad to hear NYE was a success for you and excited to hear about your weekend!

Which amazing events will you go to this weekend?

My weekend will be full of amazing moments but there will surely be no events in its forecast. Something you realize if you work in any kind of PR driven field - the events usually tend to fall on weekdays. The weekends are really necessary for all of us to unwind and stay in (at least me) with the ones we love.

O.K. Gerry, I hope this was helpful! Please let me know how your weekend in NYC goes!

-R