Jennifer Lopez Pioneers Bold New Fashion Trend & Lane Kiffin Finds His Soulmate (Again)

Anyone else struggling to function today?

I guess it's normal to drag a little bit after a long weekend. But when I opened my eyes this morning, I wasn't entirely sure what planet I was on.

See, I spent the past week drowning in rum drinks, stuffing my face with seafood and baking in the sun at Margaritaville in Fort Myers Beach. In case you missed my Nightcaps last week, my mom and a family friend planned a last-minute girls' trip to the resort and invited me to tag along. 

Never one to pass out a perfectly good excuse to drink all day and work on my tan, I agreed.

I've been going to Fort Myers Beach since I was in diapers (which, to be clear, was a few decades ago), but this is my first time staying at the house that Jimmy Buffett built.

Here are my findings:

• Overall, it's a really lovely resort, and the staff members are super nice and accommodating. There are four different restaurants/bars onsite, a gigantic pool, a gorgeous sunset terrace (my favorite spot in the whole hotel, honestly) and really cozy guest rooms that all have balconies.
• While it is right on the beach, the resort is roped off from the beach itself. I understand why they do it — so that every yahoo walking by can't just help themselves to resort amenities. But as a beach lover, I didn't like being cut off from the actual sand and water.
• Everything is stupidly expensive. This is probably to be expected at a big corporate vacation resort, but we're talking $15 each for even the most basic of cocktails, not even just the fancy signature drinks. And beers aren't cheap, either. Of course, you're not allowed to bring your own refreshments to the pool. They have someone checking bags at the front gate and won't even let you bring in your own (empty) cup.
• Don't even get me started on the price of food. I started going to breakfast at a tiki bar across the street because I couldn't stomach $18 for eggs and toast. The tuna poke was worth every penny, though.
• Oh, and there are no microwaves in the room. So enjoy your cold, expensive leftovers. If, that is, you can fit them in the mini fridge.
• The pool is a lot of fun, but it is absolutely not relaxing. So if you're looking for peace and tranquility, this is not the resort for you. If you're looking for loud DJs bumping Pit Bull's entire music library, you're going to love it there.

At the pool, they also played various games for chances to win free drinks. And not to brag, but I am the undisputed champion of holding a bucket of water at chest height with a straight arm. I won that contest every day of vacation. That's why we train hard in the gym, people! To save $15 a day on booze.

OK, OK, enough reminiscing about my tropical vacation. We're back in work mode. Ready for some Nightcaps? Let's do it.

Is Buttcrack Cleavage Gonna Be A Thing?

Yeah, we're starting this one off strong, folks.

As I was scrolling Elon Musk's Twitter today and looking for Nightcaps content, I came across a headline about Jennifer Lopez's bold, low-cut outfit from yesterday's American Music Awards. The jumpsuit came down so far on her back that you could see where the good Lord split her.

Jennifer Lopez at the 2025 American Music Awards.

(Photo by Gilbert Flores/Penske Media via Getty Images)

Well, okay then, J-Lo.

I keep scrolling and boom — another one. This time, some chick named Lily Chee is "under fire" for wearing a dress cut so low that she, too, was showing off her asscrack.

(For the record, this is my first time hearing of Lily Chee. But she looks barely even old enough to date Leonardo DiCaprio, so I did verify her age before I decided to write about her buttcrack in Nightcaps. She's 21. We're good.)

Not one… but TWO buttcrack dress headlines on the same day? What a way to come back from the holiday weekend.

Apparently, this is becoming a bit of a trend in the high fashion world (certainly not a world I'm a part of). And I just don't think I can get on board. I'm all for women wearing whatever makes them feel good, but I have to draw the line at buttcrack cleavage.

But hey, no one asks me to sign off on every new fashion trend.

So if buttcrack cleavage is the new frontier, then I owe every plumber I’ve ever hired a formal apology — and maybe a modeling contract.

Speaking Of The AMAs…

I didn't watch them.

But I did see that Beyoncé took home the awards for Favorite Female Country Artist and Favorite Country Album. And Post Malone was the Favorite Male Country Artist.

Imagine showing this to someone just a few years ago. They'd never believe you.

Shoutout to Shaboozey, though, for the bombastic side-eye when Megan Moroney said that the Carter family "basically invented country music."

Lane Kiffin Comes Full Circle

Lane Kiffin posted a photo this week making hand hearts with his ex-wife, Layla, on a boat, captioned: "Soulmates" (with an infinity symbol and a blue heart). Which is certainly an interesting way to describe the woman you divorced in 2016 after spending the better part of a decade behaving like a frat boy with a headset.

Lane and Layla Kiffin have seemingly rekindled their romance.

(Photo by Michael Kovac/Getty Images)

For those keeping score at home, Lane’s journey to rediscover love has included a whole lot of (alleged) infidelity, a well-documented post-divorce phase of dating blondes who could’ve been in the same sorority as his daughter and — most recently — a full-blown relationship with 20-something Sally Rychlak.

Truthfully, I didn't even know he and Sally broke up, so clearly I'm wildly out of the loop.

But now, apparently, the prodigal coach has returned home. Because nothing can stop true love. Not even several years of coeds, corny social media stunts, rampant cheating allegations and a midlife crisis or two.

Look, I'm not hating. Good for them.

All I'm saying is… If my husband very publicly cheated on me, divorced me to run around with a bunch of women 20 years his junior, then came crawling back to me when he got tired of making TikTok videos, we would not be making lovey-dovey hand hearts on boats.

That man is for the streets.

Pacers-Knicks Game 4 Coming Up!

Tyler B. Writes: Congrats on going up 2-0! That Yes 'Cers slogan is really dumb though.

Tyler obviously sent me this email before Sunday's Game 3 disappointment. But I'm (almost) over it now, and we are on to Game 4.

I've been on vacation for the past week, so I didn't get a chance to insufferably gloat over that insane Game 1 comeback on Wednesday. And WHAT A GAME.

I spent the first three quarters drinking overpriced margaritas at the Lah De Dah Beach Bar before heading back to the room. When the Pacers were down 14 points with less than three minutes to go, I went to the bathroom to start getting ready for bed. Yes, I clearly threw in the towel a little early.

That's when my mom and Tabitha began screaming and cheering. I could hear the broadcast over the sound of my electic toothbrush — Aaron Nesmith draining three after three after three… 

But I'm superstitious. And since the Pacers started playing lights out while I wasn't watching, I determined that I had to keep not watching. Y'all, I stayed in the bathroom for the rest of regulation and overtime — listening to the broadcast and my mom's very poor play-by-play.

It's only crazy if it doesn't work. And it worked. So you're welcome, Indiana. It was all me. 

As for the #YesCers slogan that Tyler is smearing, I actually kind of like it. Maybe I'm just blinded by fanhood. Or maybe I'm just really glad they dumped the corny "Blue Collar, Gold Swagger" slogan from the playoff days of old.

Anyway…

Stuff I Liked

OutKick Nightcaps is a daily column set to run Monday through Friday at 4 p.m.

Follow me on X / Twitter at @TheAmberHarding or email me at Amber.Harding@OutKick.com.