When AI Becomes Your Wingman… and Outdoes You

Now That There’s AI, Do I Still Need a Woman in My Life?

I found myself in a familiar situation—overthinking a conversation with a woman from a singles sailing site. Should I follow up? Should I let her take the lead? Was I about to overcommunicate again when I should just…chill?

For fun (and maybe a little validation), I decided to consult AI. I took our conversation thread and asked:

"Based on this exchange, should I follow up and ask her to pick a date this weekend, or wait for her to set one? And if I respond, what’s a message that reflects my personality?"

The AI’s response? Spot on. It reassured me that I wasn’t overstepping and even gave me the perfect nudge to move things forward.

AI’s Take on the Situation:

"She seems interested and engaged—she even said, ‘I’m sure I can figure a day or night around these days.’ That sounds like an invitation for you to take the lead in setting a date! …and she really sounds like she loves boats and the lifestyle you look to live."

1. Should I follow up?
   Absolutely! Since you’ll be leaving soon, a confident but easygoing follow-up makes sense. She’s open to meeting but might be waiting for you to suggest the when and where.

2. What to say?
   The AI suggested something playful yet direct:

"Lisa, after careful analysis of your messages, a deep dive into nautical compatibility, and a few consultations with my ship’s parrot (okay, fine, I don’t have one… yet), I’ve concluded that we should meet before I set sail to North Carolina. Since you said you can figure out a day or night, let’s make it easy—Sailor Oyster Bar, Friday or Saturday evening? I promise to keep the ‘chicks dig boats’ jokes to a minimum… maybe. But honestly, it’s pretty cool that you love boats, water, and the lifestyle so much. Makes me think my ship’s imaginary parrot might actually approve!"

Playful. Confident. No pressure. Just an invitation.

So I sent the follow-up message this AM! No longer waiting for her to respond. And yes, her name is Lisa. Which brings me to a funny side note—anyone remember The New Adventures of Old Christine? Julia Louis-Dreyfus’ ex-husband started dating a younger woman also named Christine, so they called her “New Christine” to distinguish her from “Old Christine.”

Well, I happen to know another Lisa—Lisa from Woodbine—who, by the way, still is a hottie and looks amazing (let’s be clear on that). But for the sake of organization, let’s call my sailing site Lisa “New Lisa.” No offense to either Lisa—just my way of keeping things straight.

So, what did I learn? Maybe AI can’t replace a woman in my life… but it sure can help me talk to one!!