Swipe Left on Insanity

So. You’ve survived a mental breakdown. You’re journaling, meditating, maybe even thriving or at least pretending to. Meanwhile, your hormones are hosting an illegal rave in your bloodstream. You’ve got hot flashes, anxiety, brain fog, and an ever-expanding breadbasket.

Clearly, it’s the perfect time to start dating again! In midlife. In the Caribbean. Where sarcasm goes to die, and chivalry is usually stuck in traffic behind a motorcycle convoy.

Let’s break down The Men of the Tropics™, the unavoidable archetypes when you’re trying to date with dignity (and a portable fan):

The Expat

Drinks rum like it’s character development. Had a “spiritual awakening” after his last fishing trip and thinks his Tesla SUV is a personality trait. May or may not be hiding from taxes, an ex-wife, or his own emotional accountability.

The Local

Knows literally everyone — your ex, your therapist, your cousin’s hairdresser. Says “So… we doin’ this or nah?” and considers that foreplay. Deeply prosaic in Spanish, emotionally vacant in English.

The Tourist

Here for a “life-changing experience” (read: sex with accents). Wants you to teach him salsa and take him to every beach in Puerto Rico. You match, you vibe, he leaves, and forgets your name before his TSA screening.

The Born-Again Rebuilder

Divorced. Actually reads. Says “I’m working on myself” - and means it. May overshare by the second drink. Might tell you about his inner child and share a sunset video. A rare unicorn. Approach gently.

Picture it: Thursday night in San Juan.  I’m wearing a wrap dress that almost still fits, Spanx that feel like medieval punishment, and just enough makeup to look like I “woke up like this” - if “this” means contoured, bronzed and dewy.

I’m a single, “healed-ish” perimenopausal mother of twin teentards who will only respond to my “Pineapple” SOS texts if I Venmo them cash first. Welcome to my love life: post-rehab, mid-hormones, and forever debating if that flutter in my stomach is attraction or gas.

Between the tropical humidity and your internal thermostat set to “lava,” everything feels unstable and loud. You’re sweating through first dates, questioning your judgment, and running a mental PowerPoint on your trauma history, all before the appetizer arrives.

But here’s the thing: You’re not desperate. You don’t need someone to “complete” you. You want someone who doesn’t see your boundaries as a personal challenge or label your self-respect as “drama.”

You toss out a sarcastic lifeline, and it falls flat. Communication here is a poetic dance - half salsa, half landmine. Especially when your small talk consists of treatment stories from Thailand, midlife meltdowns, and bonding sessions with teenage daughters.

The truth is, you’re not who you were before the breakdown. Or before the hormones hijacked your soul. But, you are wiser now. Less tolerant of bullshit. Content in going home alone to your dogs. Your peace is non-negotiable.

You understand what joy actually feels like now so, you’re not just dating; you’re auditioning people for a supporting role in Your Next Chapter. And if no one makes the cut? Honey, your solo scenes are Oscar-worthy.

Dating in midlife isn’t about finding “the one” anymore. It’s about not losing yourself in the process. You can laugh, flirt, and maybe even fall (just a little). But you’ll always have your standards, your savage one-liners, and your fan.

Because at this point? If he can’t handle the hot flashes, the dark humor, or a woman who actually knows what she wants - he’s not ready for the heat. Or the honesty.