Trip Talk No. 3: Ashlee's Birthday Trip to NYC
it's her birthday, she can cry if she wants to
Hi friends! I’m delighted to share Ashlee’s birthday trip with you. Over the years, Ashlee has gone from a voice in my ear1 to a writing mentor to a friend. She is just as funny and generous in person as she is on the internet.
About Ashlee: Ashlee is a wife, mother of three, believer, and the founder of Coffee + Crumbs. When she's not working or vacuuming Cheerios out of the carpet, she loves making friends on the Internet, eating cereal for dinner, and rearranging bookshelves. Her book, Create Anyway: the Joy of Pursuing Creativity in the Margins of Motherhood, is available wherever books are sold. Read more of Ashlee’s work on her Substack.
LOGISTICS:
Where did you go? New York City, NY
Was this your first time traveling to this destination? No, but we hadn’t been there since New Year’s Eve in 2011, which felt like a lifetime ago!
How long were you there? Four nights, Wednesday-Sunday.
Who did you go with? My husband, Brett.
How do you approach travel spending? The bulk of this trip was covered by points. Our flights were free via Southwest and our hotel was almost free via Marriott points we’d been hoarding since 2014 (there was still a small daily charge). Most of the trip costs involved food, Uber, and tickets to two comedy shows (Comedy Cellar / Mike Birbiglia at Beacon Theater). I taught a writing workshop leading up to this trip to help cover the extra costs. I guess that’s a long way of saying: we didn’t go into debt over this trip.
PRE-TRIP
Were you responsible for planning the trip, or did you share the responsibility with someone? How did you approach seeking input from your travel companions? I typically plan 95% of every trip we take, mostly because I love to travel, I’m an excellent researcher, and I’m super decisive. My husband would probably add that I’m far more high maintenance than he is, so it makes sense for me to be in the driver’s seat. (He’s not wrong.) For this trip, I ran a few things by Brett ahead of time, but didn’t get a ton of input aside from, “That sounds great.”
How long did it take to plan? I probably spent a few months researching stuff on and off. Total cumulative time? Maybe around 15-20 hours.
What was the most enjoyable part about planning, and what was the least enjoyable part? Most enjoyable part was researching restaurants because I love food and I equally love a good vibe/ambiance. I am the type of person who will read 25 reviews of a restaurant and then follow that up with a full Instagram deep dive before making a reservation. Least enjoyable part was probably picking which Marriott to stay at, because there were like five different ones within a two-mile radius and we were going to blow all of our hotel points on the stay. Felt like a lot of pressure to get that right!
What were you most nervous about? Getting sick and/or not sleeping well.
ON THE TRIP
What was your first impression of your destination? We stayed in the heart of Times Square, which is vibrant and chaotic in the very best way. You will not find better people watching anywhere else in America.
Tell us about a challenging moment. How did you handle it? On my actual birthday, Brett and I got into a huge fight at dinner. We were at this beautiful, bougie restaurant, and before I even knew what was happening, our conversation went completely off the rails. We never recovered. I walked back to the hotel, alone, in the rain (0/10 recommend). Brett came back 20 minutes later, at which point we talked, I don’t even know, until 1am? We worked through maybe 60% of the issue, took a break to watch the Severance season finale and eat the $35 chocolate souffle I didn’t get to eat at the restaurant, and then fell asleep. Around 4am, I woke up still feeling unsettled, at which point I shook Brett awake so we could work through the other 40%. It was a long, long night, but I’m also glad we didn’t leave anything on the table. In a weird way, I think we felt closer to each other for the second half of the trip.
What surprised you? On our last night, we met up with a friend of mine who I only knew from the Internet and ended up having the best double date with her and her husband. I knew I would love her, but I didn’t know her husband at all, or how the guys would click. We had something like a 3.5 hour dinner at a cozy Italian restaurant and the conversation never lulled. I love nights like that. We shut the place down!
Were you happy with how you packed? I was super happy with how I packed and I don’t always say that. I actually rented a few things from Nuuly for this trip (a black dress to wear on my birthday, a trench coat, and a super warm fleece) and I definitely got my money’s worth. The one thing I probably didn’t need to pack is workout clothes (“just in case I feel like going to the hotel gym”), which is my toxic trait every time I pack. Should have known that walking literal miles around NYC every day would have been more than enough exercise.
What was your itinerary?
Wednesday night: Arrive at 6pm, race to drop suitcases at hotel and immediately hop in a second Uber to get to the Comedy Cellar. Eat, drink, laugh our faces off. 10/10 recommend; iconic NY experience.
Thursday: Walk around all day, Bryant Park, The New York Public Library (fun to see where Carrie Bradshaw almost got married! IKYKY), appetizers + drinks at Broadway Lounge (in our hotel), then dinner at The Terrace.
Friday: Walk around Times Square, shopping, St. Patrick’s Cathedral, grab smoothies at Joe & the Juice, back to hotel for nap/showers, dinner at Revel and Rye (in our hotel), then Beacon Theater to see Mike Birbiglia.
Saturday: Spend the morning at MOMA (best artist date!), grab bagels at Black Seed, watch the ice skaters at Rockefeller Center, relax a bit, meet friends for double date at Osteria Del Bianco.
Did the thing you were nervous about happen? Did not get sick, sleep was … okay ;)
What do you think you’ll remember most about the trip 20-30 years from now? The birthday fight. Racing from the airport → uber —> hotel —> uber —> The Comedy Cellar and getting there with one literal minute to spare before our reservation. Laughing until our abs hurt.
POST-TRIP
What was the hardest thing for you to face when you got home? Brett left the country (for work) five days after we got home from New York. Managing that quick turnaround was pretty stressful for all of us.
Do you have any routines in place for easing back into “normal life”? Anytime I travel, I keep my out-of-office on one extra calendar day. So if I get home on a Wednesday, my out of office will say I am traveling through Thursday. That gives me a full day, mentally, for re-entry. While I definitely like to ease back into work, I’m admittedly one of those freaks who unpacks my suitcase five minutes after I get home.
Did you bring home any souvenirs? None. I went shopping on my birthday but I’m not sure a dress from American Eagle counts as a souvenir.
What did you learn about yourself through this trip? I don’t know that this was brand new information, but perhaps I re-learned that laughter is my medicine of choice, always. There are a lot of things I do to relieve stress and anxiety: reading, writing, yoga, rage-vacuuming, etc. But none of them compare to the pure intoxication of deep, unhinged, from-the-depths-of-your-belly laughter. I love live music with my whole heart, but I love comedy shows more.
Ashlee, I think I speak for everyone when I say *thank you* (and Brett!) for sharing the reality of your birthday fight. I laughed out loud when I read that you shook Brett awake to finish working through it, and I cheered when I read that the whole thing made you feel closer the rest of the trip. I’m salivating over that chocolate souffle! Also, dyyying that you packed workout clothes in case you wanted to use the hotel gym (and that this is your toxic trait).
Friends, have you ever had a fight with your husband on your birthday? (Raises hand.) Do you work out in the hotel gym? (Puts hand down.)
Though she isn’t the voice of the podcast, Ashlee also dreamed up the incredible Making a Mother series. Download these five episodes immediately!! Listen with tissues.
 | A guest post by
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The subtitle 🤣 THANK YOU FOR HAVING ME! Number of hotel gyms I have packed for: 27. Number of times I have actually worked out in a hotel gym: 2. Why am I like this!
I really appreciated Ashlee's honesty about the fight on her birthday. Also, I really need to figure out how to convince my husband he won't hate a trip to NYC. (He says it's way too many people and is also gross and dirty...I don't have many counterpoints to those, ha.)