Rudy’s would be the love of your life that you’re embarrassed to bring home to Mom and Dad. You would have met him in college; he would have had ripped jeans and scruffy hair and maybe a mild recreational drug habit. He’d be that guy that you know you should have stopped seeing when you were 22; but every time you try to end it, you can’t seem to fully disengage.

I have two favorite bars in New York City and Rudy’s is one of them. When I was looking to move into the city, I judged prospective apartments by their proximity to Rudy’s (at 44th and 9th) rather than their proximity to subway stations. What can I say? They give you free hot dogs with every drink. And if I was going to be shelling out half my monthly earnings to cover rent and utilities, I was going to need a cheap meal or two. And at 51st and 9th, I’d say I did pretty well.

A trip down Rudy’s memory lane is paved not with yellow bricks but with red duct tape, which covers the benches in every one of the tiny bar’s meager selection of booths. It starts in spring 2011 when, on a Tuesday evening when I should have been studying, I decided instead to venture into the city to meet my roommate Jackie and her art class buddies. I went out that night for a number of reasons, I guess: because I was a senior, because it was warm out, because my 11:30AM class the next day was being taught by a TA and not a professor, because my hair looked good; but most of all, although I didn’t know it yet, because I needed to go to Rudy’s.

I arrived and felt immediately at home because my $5 thrift store bright red boots perfectly matched the duct tape on the booths. I immediately ordered a $2.50 beer (Yes, they are seriously that cheap and yes, I paid in change). In my 4+-year-old black jersey dress from Urban Outfitters, I was easily one of the best dressed people in the bar, which is exactly how I like it. 

That night was full of pitchers of beer and hot dogs, and when it was time to leave Rudy’s Jackie and I, in typical fashion, parted ways with the group and headed down to our favorite haunts on the Lower East Side. Maybe it’s because there were no free hot dogs or because I had class the next day or because it was Tuesday, but that night the Lower East Side just didn’t do it for me.

Discovering Rudy’s was a revelation in that it convinced us we didn’t need to travel miles and miles downtown to have a good night. It was–gasp–possible to have a full, fun, crazy night right in midtown (though I should add that we’ve come to realize that the best nights start on the Lower East side and continue as we gradually make our way uptown).

A few of my favorite Rudy’s memories…

Taking Hunter there right after we decided to be roommates and put a deposit on our first New York apartment. If he hadn’t appreciated Rudy’s, it probably wouldn’t have worked between us. (Of course, as many of you know, that apartment didn’t quite work out, but that’s another story.)

The awkward date I had there where I ate not one but two free hot dogs  because I wasn’t attracted to the guy. (Hunter still hasn’t forgiven me for this, but the guy’s name was Sammy, so where was it really going?)

Dragging Carly and Lucien there midway during our Pride Weekend gay bar crawl and convincing Carly that the hot dogs were definitely kosher (still have no idea if that’s true).

The time the bar was at capacity and the bouncer wouldn’t let us in… until Jen jumped in with “I work at Chanel,” which got us and the girls we had jumped in front of in line into the bar.

Later that night when Erica yelled at the guy who tried to help her put Bon Jovi on the jukebox. “I can do it myself, stop crowding me!” Later, “He just wouldn’t stop pressing buttons like a fool!”

The time I hooked up with someone wearing… wait for it… manpris. Potentially my most embarrassing hook-up to date, but I don’t regret it because he had a sexy-arrogant attitude and a fabulous Soho apartment that made him the perfect 10-hour fling. (For the record, I did not see the manpris until after being captivated by his sexy hair and intriguing personality. This is the danger you face when you start talking to someone while they are sitting down.)

The time my friends decided to leave and go to another bar… and I chose to stay at Rudy’s alone instead of going with them.

The weirdest come-on I’ve ever experienced: the guy opened with “I’m gay, but if I were straight, I would totally hit on you right now,” bought me a drink, chatted a bit in a fun, gay-best-friend kind of way and then said, “Actually, I’m straight.” I excused myself immediately.

The time they wouldn’t let me in because I stumbled coming through the doorway in my sky-high wedges.

The time they did let me in even though my ID was close to 2 years expired and Jackie was yelling, “Don’t let her in. It’s a fake!” The same bouncer that had denied stumbly-Cait a few months earlier let me in that night because I was “too pretty to turn away.”

The time Jackie and I missed the 4th of July fireworks because we were sitting in Rudy’s talking to the bartenders.

The time Jackie and I crashed a “thinking Liberally” party in the backyard.

The time Jackie and I realized we could actually have a good night without leaving midtown…

(If you’re sensing a theme, it’s because Jackie is one of my nearest and dearest. We discovered Rudy’s together and made it completely our own. I love Rudy’s all the time, but it’s never quite the same without her.)

Rudy’s is a place where nobody knows your name and everybody’s too drunk to care; but for some reason, it still feels like a sort of home away from home in NYC. I’m not sure if it’s the dingy, dive bar atmosphere or the rag-tag, offbeat clientele, but I always feel pretty and comfortable and… happy at Rudy’s. And it’s always an adventure. Which is all you can really ask for in a bar.