The Bachelorette Weekend From Hell: A Survival Story

I need to tell you about last weekend. Not because I want to relive it, but because you need to learn from it. Consider this a public service announcement wrapped in trauma wrapped in rosé-flavored regret.

Names have been changed to protect the guilty. The innocent need no protection because there were no innocent.

The RSVP Situation

Let me set the scene. I'm helping my friend Caitlyn plan her bachelorette. I send out a beautifully designed email—custom graphics, clear dates, simple yes/no question—to twelve women six weeks in advance.

Responses received: Four.

Responses received after three follow-up texts: Two more.

Women who showed up at the ferry terminal on Friday morning: Fourteen.

FOURTEEN. Where did the extra people come from? Who ARE these women? One of them introduced herself to the bride. At the bride's own bachelorette party. "Hi, I'm Meghan's plus-one!" There are no plus-ones, Meghan. This isn't a wedding. This is a PLANNING NIGHTMARE.

The Child

You know what pairs beautifully with a boozy beach weekend? A three-year-old named Brantley.

Jessica—and I cannot stress this enough—brought her toddler. To the bachelorette. "My husband had a thing," she explained, as Brantley immediately began excavating the rental house's decorative sand dollars.

The bach weekend itinerary I had lovingly crafted included: wine tasting, sunset drinks at the beach, a nice dinner, and dancing. You know what it did NOT include? Paw Patrol. Chicken fingers. A 7pm bedtime that we all had to whisper around.

The rental company, bless them, found us a pack-and-play within an hour. They didn't even charge us. SAINTS.

The Cisco Incident

We made it to Cisco Brewers on Saturday afternoon. Twelve women. One toddler. One woman—let's call her "Rachel"—who had been "pre-gaming" since 11am.

Rachel ordered four drinks at once "for the table" and then drank all four drinks herself. Rachel decided the live band needed a backup dancer. Rachel attempted to befriend someone else's golden retriever with such enthusiasm that the dog hid under a picnic table.

The Cisco staff handled this with more grace than Rachel deserved. They quietly cut her off while making it seem like the bar was just "super busy right now." They brought her water and pretended it was a new specialty cocktail. Professional heroes, every one of them.

Rachel passed out in the shuttle back. Brantley drew on her face with a marker he'd found in Jessica's purse. I did not stop him.

The Dinner Reservation

I had made a reservation for twelve at one of the island's nicest restaurants. We showed up with fourteen. Plus Brantley. Plus Rachel, who had rallied in the worst possible way and was now "STARVING."

The restaurant—again, SAINTS—found us extra chairs. They made a kids menu appear from thin air. They seated us in a semi-private area, probably to protect their other guests from us. I have never been more grateful for a corner table.

The bill came. It was split fourteen ways. Eleven people Venmo'd me. One claimed she "doesn't have Venmo" (in 2025???). One said she'd "get me later." One—JESSICA—said she shouldn't have to pay full price because Brantley "barely ate anything."

Brantley ate $40 worth of chicken fingers and threw bread at a passing server. I saw him, Jessica. We all saw him.

The Aftermath

The bride had fun. At least, she says she had fun. She's either genuinely a saint or in deep denial. Possibly both.

The Venmo requests remain pending. It's been nine days. I've sent three reminders. I've been left on read by women I've known for fifteen years.

The rental house charged us an extra cleaning fee. I cannot prove it was because of the marker incident, but I suspect it was because of the marker incident.

Lessons Learned

For future reference, here is what I will be implementing for all bachelorette weekends going forward:

• No RSVP, no ferry ticket information. You want to come? Prove it in writing.
• Deposits are non-negotiable. And non-refundable. Collected six weeks in advance.
• Children require pre-approval. In writing. Notarized. In blood.
• The "Rachel Protocol": If you can't name the bride's middle name, you get a two-drink maximum.
• Payment happens BEFORE the weekend. I'm not chasing anyone down for lobster roll money ever again.

The island itself was perfect. The weather was perfect. The restaurants, the breweries, the beaches—all perfect. Everyone who works in Nantucket hospitality deserves a raise and a vacation of their own.

It's not the island's fault that some people are absolute chaos gremlins.

Anyway. If you need me, I'll be recovering. And updating my intake forms.

It's giving "never again" energy and I'm exhausted.