Let’s be honest. White tablecloth fine dining establishments are not places that you will typically find the staff of immaculateinfatuation.com. We like things a little bit looser, a little bit dirtier, and a little bit more laid back. That said, every once in a while a man needs to throw on a pair of wrinkle-free Dockers and dine like a gentleman. Every once in a while, a man also gets a gift card to a restaurant for his birthday.

Whatever the motivation, on a recent weekday night, we found ourselves heading for an Immaculate Infatuation man date at Eleven Madison Park. It was clear from the start that this would not be a typical night out stuffing our faces with burgers and pork buns. The dinner menu at Eleven Madison Park consists of different prix fixe configurations, including an eleven course chef’s tasting menu. No, this would not be another night of casual eating. This night we were going to be tucking our napkins into our collars and doing things real fancy like.

Fancy though it may be, the restaurant is surprisingly lively, and the room wide open and airy – definitely not typical of a place serving this kind of food. Make no mistake, Eleven Madison Park is fine dining at its most serious. The staff is polite, yet rigid and focused like they’re on a mission from God. I think one of them folded my napkin with his mind. While the formality of the staff can be a little bit awkward at times, their knowledge and focus is appreciated when eating at this level. The food rundown will give you the details, but our meal at Eleven Madison Park was amazing. With a menu that sources many local ingredients via the Union Square Greenmarket, from start to finish, you get what you pay for and more. Save it for the right occasion. You won’t be disappointed.

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The more I read about Mas, the more it became clear – Mas needed to be my next fine dining destination. So to celebrate my 29 years on this earth, Mas got the call. After witnessing what appeared to be an ecstasy induced seizure by a fellow food freak at the mere mention of Mas, I knew this was the right move. Literally she was foaming at the mouth, eyes rolling into the back of her head, and nearly falling out of her chair as she attempted to recall her glorious meal. It was one of those “holy s–t, I immediately need to see you do that again” moments.

With high hopes and empty stomachs we rolled up seven deep and sat at Mas’ lone big table. My only complaint about the table was that we were in direct line with the air conditioning which was pumping right on our faces the whole time. Not the most comfortable way to spend a meal. The design is one that can only be described as modern rustic. A seamless blend of wood, stone, and mirrors produces a subtle elegance. The service was superb and our waiter was laid back and informative. Quite impressive and accommodating is the fact that, for their four-course $68 price fix tasting menu (one app, two mains, one dessert), you can pick anything from the menu. We sampled just about everything on the menu and the result was one of the better meals I’ve had in a long time. Let’s get down to business.

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Upon entering Commerce the urge to start drinking immediately fell over me. Probably because the last time I was in this space it was the legendary NYC watering hole Grange Hall. Plus, maneuvering through the labyrinth of these West Village streets will drive even those blessed with a keen sense of direction to head straight for the bar. Commerce was warm and welcoming; we were seated within ten minutes and found the service to be spot on. The dark walnut tables, cozy throwback booths, and murals decorating the walls work to restore this classic venue. Upscale American comfort food plays very well off the decor and prompts an obvious comparison to a less hip, more authentic, west side Freeman’s.

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It’s rare that I, or anyone else in NYC for that matter, actually venture to the UWS to eat out. Those treks north are usually reserved for Bar/Bat Mitzvahs, chocolate chip cookies (I love Levain Bakery and Jacques Torres), and takeout essentials from Artie’s Delicatessen or Fairway. Thanks to Dovetail, there’s now another reason to make the trip.

Dovetail has been written up everywhere as one of 2008’s best new restaurants, so when it came time to pick a place to go with Mom and Grandma for my brother’s birthday, Dovetail was the call. Though I’d read a bunch of reviews that said the service at Dovetail was terrible, we experienced the complete opposite and were treated like royalty from the moment we stepped foot in the door. Our server was the man, and it felt like we had three of our own bus boys taking care of our every need. Left over crumb on your lip? No worries, they got it. The food was consistently great across the board and everyone at the table enjoyed their meal.

Dovetail is expensive, but not obnoxiously so, and once you’re inside you won’t remember you’re on the UWS, as the exposed brick and rustic artwork give the restaurant a very downtown feel. The food and service are both great, and overall, Dovetail is highly recommended.

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Five Points should have been one of the first reviews up on Immaculate Infatuation. The fact that it had to wait until slot #126 is completely our bad. It’s one of the most reliable and universally likeable restaurants we’ve been to, coming through in the clutch time after time. Need the ultimate place to take your mom when she comes into town? This is it. How about a centrally located spot for a business dinner downtown? Check. Date night? Absolutely. Better yet, make a day of it. Play hooky from work with your current love interest, get a massage at Great Jones Spa next door and follow that up with lunch. Now that’s the start to a quality day. Although it’s not in the food rundown below, brunch at Five Points is top notch.

Not only is their menu updated seasonally, the entire restaurant goes through a transformation. Everything from their drink menu to the decor changes with the seasons. Personally, autumn is my favorite time to come here with their leaf filled branches, strategically placed pumpkins and gourds, apple cider drinks, pork chops, sweet potato mash and pumpkin desserts.

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