Wingmen by the Stars — and by the App: Astrology, Pitch‑A‑Friend, and the Business of Being There

I admit it: I enjoy the playful certainty that astrology offers. When someone tells me, "Aries make the best wingmen," there's a small part of me that wants to nod and order another cup of tea. Personality shorthand — whether zodiac signs, Myers‑Briggs types, or decades of lived friendship — gives us a quick map to the human terrain.

But lately I find myself standing at an intersection of three trends and asking a quieter, more urgent question: as we slice human connection into categories and products, what happens to the people behind the labels?

1) Zodiac as shorthand — useful, but limited

People love lists: "best wingmen by zodiac" is the kind of list that travels fast because it promises an entertaining answer to a common problem — how to help a friend shine in a social moment. Astrology can point to tendencies: bold Leos who will introduce you, witty Geminis who riff with strangers, dependable Tauruses who steady the conversation.

And yet, a sun‑sign doesn't teach empathy, discretion, or emotional availability. A good wing is less about fixed traits and more about attunement — reading a friend's nervousness, knowing when to nudge and when to step back.

So I treat astrology like a menu, not a mandate. Fun, clarifying, helpful for a quick filter — but not a substitute for real social skill and care.

2) The Pitch‑A‑Friend movement — curated friendliness as performance and service

That is why I found the Pitch‑A‑Friend phenomenon so interesting. A recent article describes how people now pitch their friends with short PowerPoint presentations at events, turning the humble wing into a curated performance for a roomful of potential matches Pitch‑A‑Friend Is A Viral PowerPoint Dating Trend. The organizer in Seattle imagined friends as advocates; others took the idea online and made it an event format.

I recognise something of my earlier thinking in this: years ago I wrote about a platform called COUCH — a place to let lonely people find listeners and to let listeners earn small incomes by offering empathic conversation (Share Your Soul / Outsourcing Unlimited). Pitch‑A‑Friend is a cousin idea: it formalises the role of the friend as curator and advocate.

There is a generous and even brave logic here. Friends often want to help each other meet better people. Giving a friend five minutes — or a five‑slide deck — to explain why someone is worthy of attention forces a different kind of thoughtfulness than the typical "she’s great, trust me" passoff.

But it also turns friendship into a staged transaction. That’s not bad by default — staging can amplify the virtues we already have — but it raises questions about authenticity, consent, and accessibility.

3) Rent‑a‑friend, paid listeners, and AI wingmen: the commercialization of presence

If you read something I wrote some years back you’ll know this is not new to me. I tracked the growth of "rent‑a‑friend" services (I wrote about it in Share Your Soul) and sketched a marketplace for paid listeners long before the recent boom in apps. After Covid I could see the demand explode — loneliness is a global problem and many people will pay for a compassionate ear (You Lonely of the World — Come to Me).

At the same time, the arrival of AI companions — chatbots trained on a person’s voice or persona — has been dramatic. The Economic Times recently summarised this new wave of AI relationships; people are already using apps that provide remarkably lifelike companionship New‑age relationships: it’s virtually saying ‘AI love you’. I wrote about this evolution too in Virtual friends — better than no friends? and I confess: it validated something I had predicted.

AI wingmen will be able to handle the logistics — suggesting icebreakers, reading social signals, or privately coaching you through a conversation in real time. A human wing and a digital wing are two different muscles. The digital one can be trained, scaled, and polished; the human one brings moral judgment, warmth and unpredictability.

Where astrology fits into this new economy of presence

This brings me back to the zodiac list. If people enjoy categorising winging styles by sign, why not do the same to design better social systems:

• Use personality heuristics (zodiac as shorthand, psych profiles, social history) to match human wing‑helpers to the situations they handle best.
• Combine human wingpeople with tech nudges: a "cheat sheet" app that whispers tailored prompts to a wing based on the friend they’re supporting.
• Offer curated training and moderation (rates, privacy, escalation protocols) so that paid listeners and wing‑helpers operate ethically.

In other words, astrology can be a lightweight filter in a larger, safer system that values consent and wellbeing.

Practical cautions — privacy, mental health, and dignity

If you’ve read my old notes, you know I often lean into opportunity. I believe platforms can create work and connection. But I am not starry‑eyed. There are real risks:

• Privacy: recordings, persona models and pitch decks contain sensitive details. Any platform selling presence must protect data vigorously.
• Mental‑health substitution: paid listeners or AI companions are not a free substitute for clinical therapy. They can help, but they must not pretend to be professional diagnosis.
• Commodification of care: when empathy becomes a gig, we must watch for exploitation of both sides — workers and customers.

That is why, when I proposed a COUCH‑style portal years ago, I insisted on reputation systems, recorded histories, moderation and a clear boundary between peer support and clinical care (Share Your Soul). Today those choices feel more urgent.

A small manifesto for modern winging

If you ask me whether a horoscope can tell you who will be your best wingperson, I’ll answer: perhaps, in a pinch. But if you ask what we should build around that curiosity, I’ll say this:

• Treat personality tags as tools, not shackles. Use them to orient, not to dictate.
• Curate and train: whether volunteer friends, paid listeners, or AI assistants, give them frameworks for consent, boundary‑setting, and escalation.
• Protect dignity: ensure privacy, transparent pricing, and clear role descriptions so nobody is misled about what the service offers.
• Keep care human in the loop: AI can scale presence, but human oversight and access to professional help must remain central.

Why this matters to me today

When I wrote about these ideas years ago — the rent‑a‑friend platforms, the COUCH idea, the market for listening — I was asking a simple question: how do we match spare human goodwill with people who are lonely? Watching things evolve (from Pitch‑A‑Friend events Pitch‑A‑Friend Is A Viral PowerPoint Dating Trend to AI companions) I feel a curious mix of validation and urgency.

Validation, because the demand I foresaw has indeed arrived. Urgency, because scale amplifies both the good and the bad. The core idea I advocated years ago — that we can design systems to share listening and care — is still relevant and still actionable. The time to get the details right is now.

If you enjoy lists that tell you which zodiac sign will be the funniest wingman, enjoy them. They are tiny rituals that help us talk about what we want in a friend. But let’s not stop there. Let’s build platforms and norms so that, when a friend needs a wing — human or digital — they land in arms that are competent, compassionate, and accountable.

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Regards,
Hemen Parekh