Kristin Cavallari Goes Nips Out For Summer, Annie Agar Hits The Beach & MAGA Bikini Congresswoman Turns 36!

First Hump Day of May? That'll play. Oh, that'll play. 

Big day for the Dean house. We start sleep boot camp tonight with our 8-month-old. That's right. Sleep training. Never had to do it with my daughter, because A) she's a girl and girls are so much easier, and B) she just slept like a regular human. Still does. 

My son … does not. At all. He hasn't slept through the night since Christmas. Coincidentally (not at all), I haven't slept in my bed, through the night, since Christmas. 

I ain't built for that life. Some parents can just go through life co-sleeping. I cannot. The First Lady can't, either. So, we brought in an expert, and Night 1 is tonight. I assume we just let him cry it out, but it ain't up to me. So, we're doing something called "the chair method," where we sit by his crib until he falls asleep on his own. 

And by "we," I mean "me," because I was told dads handle this portion of the training much better. So, I'm looking forward to sitting in a dark room for hours tonight listening to my son cry, instead of having sex and watching something Gordon Ramsey-related. Can't wait!

Anyway … welcome to a Hump Day Nightcaps – the one where we flash some leather with Kristin Cavallari, and go from there. 

What else? I've got the MAGA bikini congresswoman celebrating a big birthday, a crab video that has the internet divided, Trump stuffing the new Canadian PM in a locker and Annie Agar enjoying a pre-summer beach day. 

Whew. What a MENU. We're rolling today. Let's have a big class. 

Grab yourself anything alcoholic – none for me since I'm clearly not sleeping tonight – and settle in for a Hump Day 'Cap!

Solid day of golf #content

Gonna go ahead, spin the wheel, and start with … golf! We're one week from the PGA championship at Quail Hollow, so let's get the vibes in order as we barrel towards the second major. 

I golfed yesterday for the first time since my career-best 84 and shot … 42 … over nine holes. Good with me! I believe that's also 27 straight holes with the same nugget, another personal-best. What a run. I know it's gonna end soon, and that makes me sad. But boy, it's been a pleasure. 

Anyway, how about the balls on Justin Bieber A) showing up to a golf course looking like this, and B) showing up to a golf course looking like this, and swinging like this:

My God. Imagine seeing that on the course? Even at my crappy local course, you don't see that. Have some self-respect. And if you're gonna look like a prick, at least have the decency to get off the tee better than that. 

And here's the part that's really gonna piss you off … the internet tells me Justin was playing at California's Madison Golf Club, where membership starts at a measly $500,000. 

The kicker? Apparently, there is no dress code … at all! What world am I living in? Has anyone in this class ever played it? Or know someone who played it? It's a longshot, I know, but figured I'd ask. Seems wild. 

Anyway, while Justin was hitting duck-hooks out west, this hero wasn't about to take a penalty because of some stupid wedding:

Where do we stand on this crab recipe? 

Brother, I've been there before. Oddly enough, at the same course I played yesterday. 

Long par 5, I'm on the top of a fairway bunker, and absolutely shank it right to the edge of a wedding on the far side of the fairway. One of the scariest moments of my life. The ball was in the air for hours, it seemed. I saw everything flash right before me. I've never felt so helpless. 

And if you think I didn't pick that ball right the hell up after shanking my last shot, think again. I've never picked one up faster. I don't have the nuts for that. 

So, kudos to this legend for playing right on through and tuning out the noise. He's got to find a way through these trees and back to the fairway, and he ain't letting some wedding stop him. Even takes a few practice swings. Locked in. Love it. 

OK, let's get to a video of some TikTok chick with crabs! 

Kristin, Anna & Trump, oh my!

So, the keyboard warriors are out to get this chick today. They're pissed. PETA is probably calling for life in prison, knowing those lunatics. 

I think I'm OK with the move. Don't love the visual aspect of it, but it is what it is. I'm not going to sit here and wax poetic about the dos and don'ts of eating animals. I've seen plenty of live crabs thrown into a boiling pot, so I'm not sure if this is any different. 

For what it's worth, Google tells me that the humane way to murder a crab is to stick it in the fridge first to numb it, and then stab it. I'll admit, that sounds like a better way to go than being burned alive, but neither sounds particularly great. 

Anyway, Bon Appétit! Let's go ahead and rapid-fire this Hump Day class into a sleepless night. First up? Not enough hot girls today. That changes … now!

Welcome back to class, Kristin! Been a MINUTE, but it was worth the wait. Love the new gear. Looks like summer, feels like summer, hits like summer. I think we're in for a big few months of #content out of Jay's ex-wife. She's single, again, and that means she's a loose cannon. 

Last year she was with Montana Tech's Mark Estes. But now? The girls are back out to play. Let's roll. 

Next? I'd be remiss if I didn't wish Nightcaps OG, Anna Paulina Luna, a very happy birthday! Our favorite MAGA Bikini congresswoman turned 36 yesterday, and – fortunately – she looks it!

Not your average breakfast taco! No clue what it means, but I'm all in. Happy birthday to a legend. The citizens of the Sunshine State are proud to have you backing us up there in the swamp! Keep up the good work. 

Speaking of D.C., let's quickly check in on how Trump is handling the new Canadian Lib in charge:

Take us home, Annie!

Yeah, this guy is cooked. He doesn't stand a chance. Trump chewed him up and spit him out yesterday for about 45 straight minutes. Absolute bloodbath. 

Oh well. Another one bites the dust. 

OK, that's it for today. Solid Hump Day to start May. I have to go prepare for war. 

Take us home, Annie Agar!

OutKick Nightcaps is a daily column set to run Monday through Friday at 4 p.m. (roughly, we’re not robots).

Your gone through sleep training before? Email me at Zach.Dean@OutKick.com.