One of my best friends, Riley, celebrates her 26th birthday this week and I celebrate my 30th on Thanksgiving, so we decided to plan a girls’ trip to Chicago before the holiday craziness begins. It was a weekend full of characters and memorable quotes. We left Chicago thankful for our friendship and inspired to plan more one day vacays. Time with my best friends was the best 30th birthday gift and as Riley and I blew out our candles on Saturday night, we remarked that we’re all at a really good place in life.

We have men that support us and make us happy. And we have each other. You read that correctly – I am dating someone that for the first time in a very long time, makes me ridiculously happy. I hadn’t told my friends until this weekend because I didn’t want to jinx it and I also don’t want to elaborate too much here, but I’m the luckiest and now I’m eagerly counting down the days to my 30th instead of dreading it.

There are so many moments that I wish I could share with Denver and while she’s not here, I am content knowing she would be ecstatic knowing that I am happy. My new man knew Denver and while that is not a criteria for a boyfriend, I love knowing he has perspective of how incredible she was. We both went to IU, lived on the same street (greek life), did student government, and yet we never met until now. Life is all about timing. So, 30 is to new beginnings.

Now onto our epic weekend. Here’s a rambling re-cap:

On Saturday we went to The Red Door for brunch. The first step was getting there. Our Uber driver, Paul (from Brooklyn), spent a good 45 minutes with us as we discussed online dating, why Indy is actually the best city ever (Sorry, Chicago), and sports. We knew instantly we would all be fast friends when he said, “You guys can’t be from Chicago because you’re too nice.” I have to say, we’re a group of kind ladies. Just wait until you scroll further down for the homeless cat story.

He also schooled us on engagement rings. “Nothing under $14,000 for the ring will do,” according to Paul. Note: Paul is single and has proposed to every girl he has ever dated. He also asked if we were drunk when we got in the car. Nope, completely sober. Just high on life, Paul. This was before the bottomless mimosas at Red Door.

Brunch was good…..once we finally got it. We received our food about three hours after we ordered it and we shut down the bar. There were tons of empty tables and I am still mystified as to why we couldn’t sit at one, but I digress. After plopping down at the bar, we ordered the bottomless mimosas for $14 and placed our order. Our bartender, Danielle, became our new BFF and distracted us with complimentary fireball shots since the kitchen apparently took a three hour break. Once we did receive our food, we could not shove it in our mouths fast enough.

I ordered an omelette with fries. They were out of pancakes and the fried green tomato for the french toast sandwich, which was not apparent until about an hour after my friends attempted to order both.

Overall, we were glad we ate there and full when we left. Danielle is a firecracker and we heard her life story over those three hours. She even snuck a Filthy cherry to us, which is apparently an expensive garnish. She also participated in the Fireball, so we tipped Danielle accordingly.














Next, we strolled the streets of Bucktown and I ended up buying a sassy dress on sale for $42 (instead of the original $158). It’s a little low cut and not my normal Libby wear, but the pockets sold me (see below for dress). Gotta have some place for your hands….and a snack. Bar food can be pricey.

We quickly Ubered back to the Fairmont to get ready for our night out. The girls straightened my hair and did my make-up. I always feel like I look nothing like myself and should carry a sign that says, “I don’t usually look like this” as a disclaimer. It was fun to have a night out, but it also made me appreciate that I can wear zero make-up everyday and still feel beautiful.

I made reservations at RPM Steak well in advance and I am so glad I did. It’s a fancy steakhouse with two Chicago locations – the other one is Italian. The service was very good and we felt pretty fancy in our leather booth. We ordered salads: the wedge for Ali B/Riley and the chopped for Ali N/me. Add some of their Parker bread rolls and it was a filling meal. We decided to pass up the $150 steak for the table.

Our server, Drew, was really personable and pulled out all the stops for our birthdays. A s’mores sundae with candles, plus cotton candy for kicks, arrived at our table for the finale. Drew also shared his fashion secrets with us: “So, I bought these Lucky Brand jeans with spandex in them.”







Next we went to the Palomar for their bar called the Sable. Then onto Three Dots and a Dash (I found it underwhelming, but I was also claustrophobic at the standing room only bar), and then the Fremont. The last bar of the night had some interesting gentleman and I felt especially lucky to be taken. “I’m in love with you. I’m Irish.” That’s just one quote from the night among many.

The girls at The Fremont, plus Ali B’s friend, Chelsea. She’s a hip graphic designer and she made our weekend a lot of fun.

At some point in our bar hopping, Riley found a homeless man with a cat in his backpack. We had to walk back so that she could give him money. “Here’s $2 for your cat. Fancy Feast is 57 cents a can, so you can get at least three cans.” Just one more reason I love my friends.

When we got back to the hotel room, a birthday cupcake and a bottle of champagne were waiting for us. Huge props to the Fairmont and Mark at the front desk for making our weekend memorable. Mark was the one that immediately turned to Ali B and said, “You’re the troublemaker” when we checked in. Sounds about right.

The view from our room


Our last meal of the trip was Sunday brunch at Wild Berry. The wait was crazy, but I am sure Chicagoans are used to it by now. “You’ve been waiting 45 minutes and the wait is 60-80 minutes, so go wait until we text you,” said the Wild Berry lady. Our server was not the nicest or the savviest. We had to explain our orders a few times and she wasn’t particularly happy to be there. She even removed the comment card from our table because she probably sensed we were not amused.

The food was really good and we ate ourselves silly. I expected it to be subpar based on the chain restaurant decor, but the omelette with goat cheese, avocado, and sundried tomatoes was the best I’ve had in a long time. Add pancakes, hash browns, and toast for an ideal hungover feast. We crossed the street to Millennium Park for a quick pitstop to see the Bean and then we hit the road back to Indy!

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Words of wisdom from a sweet work colleague

Xx, Libby (and Winston too)

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