Looking for love in all the wrong algorithms

Can AI help in matters of the heart? Lord knows I could use it.

I have a confession.

For nearly a year, I have been using a dating site, which shall remained unnamed (but rhymes with Stumble). It would require half of Roget’s Thesaurus to fully express all of my feelings about this experience, so I will just stick with the D’s: despairing, dejected, dismayed, depressed, despondent, disheartened, discouraged, and deflated. Definitely not delighted or delirious.

In that time I have conducted an in-depth analysis of the women who have swiped right on me. Turns out I attract two types of women: psychotherapists, and those who’ve recently escaped from prison. [1] The only logical conclusion: I either represent a career-advancing analytical case study, or they’re looking for someone to drive the getaway car.

There is actually a third type: An Asian pixie with limited grammatical skills who has some intriguing investment opportunities she’d like to discuss.

ICYMI: Your smart car knows when you’ve had sex

Apparently I am doing something very very wrong with my dating profile. It could be the casual references to serial killing (joking, obviously) or when I admit that sarcasm is my love language. [2] But whatever it is, I could use all the help I can get. So — and, yes, I know this will surprise you — I turned to generative AI.

Swain in vain

I created a list of adjectives that I wanted the AI engine to include in a profile describing yours truly. I then asked each artificial brain to conjure up three 100-word descriptions that would make me sound like catnip to the ladies.

Here’s ChatGPT’s first attempt:

I know what you’re thinking. How can a guy this suave, humble, and towering still be single? It’s a mystery to me, too. On the other hand, If you’re ever seeking an example of an AI ‘hallucination’, this would do nicely.

Bing’s AI powered chat/search engine offers profile blurbs in three flavors: creative, balanced, and precise. Here’s the ‘precise’ version:

I especially like, “My humility is my charm, and my charisma, irresistible.” [4]

My egotism is my super power, and my doucheyness, inescapable.

I am beginning to understand why I can’t get a date.

Bard goes hard

Onto Google Bard, where things do not go much better.

Bard started out by throwing a bit of shade — after I fed it my list of adjectives, it responded with “that’s a lot to live up to” — and finished with some momish dating advice: “Be honest and upfront about your preferences, so that you don't waste your time or the time of others.” F**k you too, mom.

Despite the Craigslist-style headline, this one was probably the best of the three. In Take no. 2, Bard repeated the phrase “tall, smart, sexy, and funny writer” three times in 100 words, which would be a really effective technique if I were trying to date a search engine. (Sorry, Google – I’m just not that into you.)

ICYMI: My AI girlfriend is smokin’ hot, but also kind of shallow

For Take no. 3, I went for Bard’s ‘casual’ option. This time it changed a handful of words and added a winking emoji after the last sentence (“I have a zero-tolerance policy for Trump supporters”) to, in Bard’s words, “show that you’re joking.” [4]

Uh, Bard? Not joking. Serious as a heart attack about that.

Claude’s no fraud

Claude is a relative latecomer to the Gen AI chat wars and far less known than the other three. Still, its tech-daddy (and OpenAI spinoff) Anthropic was one of the AI firms invited to brief Congress last month. The version 2.0 beta was released in July, so I decided to give it a go.

Claude did a fine job first time out, save for one small detail: It flipped genders on me. There’s absolutely nothing wrong with that, save for the fact that I’m not “a 420 and wine-friendly gal [who] wants someone who's smoke-free and left-leaning... [and] a fellow bookworm who likes snuggling up to binge-watch shows. Must love dogs!”

This is despite the headline above it saying “smart, sexy, funny gent.” Apparently between the headline and the body text Claude believes I underwent an exceedingly unlikely & alarmingly rapid transition. And where did that line about dogs come from? [5]

Of the 12 or so options, I am leaning toward one of Claude’s suggestions, with a few edits. (Starting with deleting the word ‘humble.’) Then I’ll post one of these to Crumble-Fumble-Tumble and see if the bots are any better at using these dating sites than I am. [6]

What AI dating coach would you use? Leave your picks in in the comments below.

[1] The neck tattoos are a dead giveaway.

[2] I am scrupulously honest in my dating profile, with the exception of my age, height, body type, and fondness for cuddling.

[3] F**k you, again, Bard.

[4] That last comma after ‘charisma’ is <chef’s kiss>.

[5] Of course I love dogs (except for the little yappy ones). I’m not a monster. But how would Claude know that?

[6] If you believe this entire post was simply an attempt to fool the algorithms that control our lives into associating my name with the words “smart, sexy, and funny,” well…. Lovely crisp weather we’ve been having lately, eh? Really starting to feel like fall.