Chelsea Kaplan’s Musings About Life... After Birth

My amazing cousin Kate is getting married next month, and this weekend I'm flying to Chicago for her bachelorette trip. Shenanigans are sure to abound.

I'm Katie's Matron-of-Honor. (Gah..."matron." What an ugly word. It's like the name "Hulga." It makes me feel frumpy just saying it.) I am beyond excited about this honor, and I'm even more excited that Katie asked each of her bridesmaids to find a black cocktail dress we love to wear to the wedding, rather than making us each spend a gazillion dollars on a frothy confection that will just take up space in our closet. (Fist bump, Kate.)

This isn't the first wedding I've been in...in fact, I'm pretty sure it's my fifth, but I feel like I'm missing one in my mental roll call. And I've been on countless other bachelorette trips. As I'm getting ready for this weekend, though, I'm reflecting on how my maturity level has evolved since I first entered the realm of bachelorette parties about a decade ago. (Ouch.)

When I was roughly "21" (sorry, bouncer man) and prepping for a bachelorette party, I remember thinking thoughts along these lines:

• Does this pushup bra push up enough?
• I hope we remember to take a group picture in the bathroom!
• Do we have enough decorations with penises on them?
• ZOMG we should make the bride wear a tutu because that's THEFUNNIESTTHINGEVER!
• Okay, NOW my pushup bra pushes up enough. But where am I going to stash my keys? (Lightbulb!)
• He is so.cute. Which one of us gets to kiss him?
• Is my skirt too short? Cause I can make it shorter.
• These stillettos are FIERCE! Sure, I may break my ankle, but hey, if they get too uncomfy I'll just take them off! Because going barefoot in a bar isn't trashy at all.
• I have TWENTY BUCKS! How many beers can I get with that????
• The bar closes at THREE? Then what???

Now that I'm 31 and packing for the trip, here's the thought process:

• A weekend without my kids! Wahoo!
• Wait...I'm really gonna miss my kids.
• Can you tell I'm wearing Spanx with this dress?
• I hope my kids are okay without me.
• These shoes are perfect with this dress...but the heels may get really uncomfortable if we go dancing. Maybe I'll just wear the flats.
• My husband is gonna feed my kids nothing but junk food and I'm going to come home to diabetic gremlins.
• Oooh, before we go out dancing, let's do something fun like take a painting class! (Stop laughing. We're really doing that.)
• I can't wait to spend some good quality girl time. I hope we get a chance to talk.
• Gah, I'm gonna have to remember to pump before we go out so my boobs don't explode.
• Let me make sure I have enough cash in case we have to take a cab...
• My husband better text me a ton of pictures of the kids.
• The limo's picking us up at 1am? Gulp...maybe I can take a power nap in the bathroom.

Whew. I'm so glad I'm not 21 anymore.

But who am I kidding? I'm not that mature. We're gonna party like rockstars. And I promise to post pictures.

How about y'all? How has your party style matured, other than having the financial means to splurge for the fancy drinks?

Although it’s taken me several weeks to recover, the bachelorette trip I went on in Chicago was worth mentioning. (I must note that it was more sleep deprivation and less alcohol I was recovering from. If I go to bed anytime after 11 my wake cycle suffers. I? Am a toddler.)

The trip was to celebrate my cousin Katie, a special lady who’s getting married this upcoming Saturday. I hadn’t met any of her friends before the party, but had a blast getting to know them all. By the time the weekend was wrapping up we were all fast friends, and I’m looking forward to seeing them this weekend.

In planning the trip, I aimed for a fun but adult approach to the weekend. (Read: nothing phallic.) I would have done anything to make the weekend what Kate wanted, but luckily she was on-board with a classier approach.

Part of the fun of a bachelorette trip is always sweeping through the city en masse, feeling like the world is your party and everyone else was invited to celebrate. To achieve this, it’s important to dress up. Katie’s wedding is going to have an elegant, vintage vibe, and I wanted to tie into that. We requested that the guests all wear black, with the bride-to-be in white. (Throughout the night, we had multiple people ask which of us was the bride. This amused me.) Here are some of us right before the limo picked us up.

The rest of our party met us downtown. The dog stayed home, along with Katie's dog daughter Ramona, who guarded the bow bouquet. (Isn't Ramona the perfect name for a pug?)

I love the fascinator trend, but didn’t see any that were exactly what I wanted, so I made one for each of the guests. (They were simple…hot glue all the way.) We gave these, along with masses of white beads, to each of the guests. Simple, elegant, cheesy. Check.

For Katie I made a birdcage veil. This was fairly simple. I would encourage anyone to at least attempt to do it themselves, but be prepared for it to take several attempts to get it just right. Add a skinny feather boa, and Katie looked amazing. Just getting dressed up and hitting the city with this lovely group of women would have been a fun enough experience.

However…

We wanted to do something fun and memorable during our event other than dancing (although that came later, make no mistake). Kate has some education from the Art Institute under her belt, so after a lot of fun brainstorming (Kentucky Derby? Belly Dancing lessons?) we opted for a private painting class at Bottles and Bottega in Lakeview.

The venue was beautiful…lots of windows so you could see the city. The staff was amazing…the owners worked with me and another bridesmaid (in Georgia and DC, respectively) to plan the event and the owners, Stephanie and Nancy, couldn’t have been more helpful. They host regular events, not just private parties, so if you’re in the market for a fun date night in Chicago (with you SO or your girlfriends), this would be a great place to do it.

We catered in food and brought our own wine. We each painted the same picture, although our results were all widely different. (Katie’s was gorgeous and I schemed to switch ours out, but was foiled in my short career in art thievery.)

Here’s the lot of us…aren’t we lovely?

The rest of the evening involved more traditional activities, such as cramming too many girls in a cab. We read that Snoop Dogg was in Chicago that weekend and attempted, through a iPhone/Twitter/Facbook bomb, to get him to join us in our shenanigans, but he was a no-show. In hindsight, I think perhaps that was for the best.

A visit to a Sidetracks, a gay bar in Boystown, was next. This bar was clean and lovely, and had amazing Arnold Palmers…for only $5 a pop.

A note on gay bars on bachelorette trips: I recommend them highly if you’re interested in avoiding too much attention and focusing on your friends, as we were. The other patrons were friendly but respectful. We did chat with one couple that made me laugh…the blonde gentleman introduced me to his Italian boyfriend and gushed, “He’s from Italy. He knows the Pope.” Which makes absolutely logical sense. Since I’m an American and by the same logic should be acquainted with Michelle Obama. (Should I feel slighted we have yet to have dinner?)

The night concluded with a trip to Hangee Uppee, a dirty, loud, overcrowded bar that played every song you ever forgot you loved. They didn’t serve white wine, my shoes stuck to the floor, and around midnight as we sang “Love Shack,” (Tiiiiin Roof! Rusted.) I realized I was quite ready to go. Can you tell?

Katie danced on the small stage, artfully avoiding the advances of every drunk male willing to offer his services for her last hurrah. However, two hilarious guys joined Katie for an impromtu air band with Katie on bongos, a trombone, and a guitar. This performance will remain one of my favorite memories. Unfortunately the camera batteries died at this point, so I don’t have any pictures to share.

Great memories were made, and I’m looking forward to the wedding this weekend…although I’m traveling up early with the three kiddos so The Husband can finish the work week, so expect a whole other post on that.