Category: Reporters – Sydney Bradley

222 Uses AI to Match Strangers at Real-Life Events

Posted on March 24, 2026
222 logo

BUSINESS INSIDER – Startup 222, founded by Keyan Kazemian, Danial Hashemi, and Arman Roshannai, is building a different approach to dating by focusing on real-life interactions instead of swiping. It launched in 2021 as a dinner series in LA, matching strangers using AI after personality assessments, then grew into a company, joined Y Combinator, raised capital, moved to New York, and launched an app in 2024. The product matches people into small in-person experiences like dinners or nights out, then collects feedback to improve future matches and sets up follow-up dates if there is mutual interest. It has since expanded beyond first meetings into helping maintain relationships. In 2025, it raised another $10.1M, bringing total funding to $13.7M, and is now investing in tools that drive ongoing real-world connections, not just introductions.

See full article at Business Insider

Partiful Adds “Crush,” Turning Party Invites Into a Dating Signal

Posted on January 15, 2026
Partiful Crush

BUSINESS INSIDER – Partiful, a party-invite app, has introduced a new feature called Crush that lets users discreetly express romantic interest in people they have met at real-life events. Users can select mutual connections as crushes, and only if the interest is mutual are both parties notified and encouraged to message each other, with a limit of 10 crushes per month. The move reflects a broader trend of non-dating apps evolving into dating-adjacent platforms, as people increasingly use social, professional, and event-based apps to flirt and connect.

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Testing AI Matchmakers: More Structure, Same Dating Fatigue

Posted on January 5, 2026
AI matchmaking

BUSINESS INSIDER – Two journalists tested four AI matchmaking services – Amata, Facebook Dating, Sitch, and Three Day Rule – to assess whether chatbot-led matching improved dating outcomes. After weeks of interacting with AI matchmakers, reviewing suggested profiles, and going on several dates, the conclusion was that AI added structure and convenience, such as slower matching, automated profiles, and date planning, but did not eliminate dating fatigue or materially improve results. Some dates occurred, mainly through Amata and Sitch, but overall the experience felt like a modified version of traditional dating apps rather than a fundamental change.

See full article at Business Insider

Dating Apps Turn to AI After User Growth and Revenue Declines

Posted on December 29, 2025

BUSINESS INSIDER – Dating apps including Tinder, Hinge, Bumble, and Grindr are investing tens of millions of dollars in AI-powered matchmaking to counter swipe fatigue, declining engagement, and falling paid-user numbers. Match Group’s stock is down ~75% over five years and its paying users fell 5% YOY, while Bumble’s share price is down ~50% this year, it laid off 30% of staff, and paying users dropped 18%. The companies are deploying generative AI for matchmaking, profile creation, flirting, and safety, with Tinder testing its Chemistry feature and Grindr launching AI-driven recommendation feeds. Analysts say AI alone cannot revive unpopular products. At the same time, AI-first startups are raising capital and entering the market, including Sitch, which has raised $9M and charges $90 for three matches, alongside new apps such as Known, Ditto, and Amata, while Facebook has introduced an AI dating assistant.

See full article at Business Insider

Keeper: AI Matchmaking Startup Charging Men Up to $50,000 for Marriage Matches

Posted on December 16, 2025
Logo of Keeper, an AI matchmaking startup specializing in long-term partner identification

BUSINESS INSIDER – Keeper is an AI matchmaking startup that claims it can identify a person’s ideal long-term partner with high precision, and charges men up to $50K if a match leads to marriage. Launched in 2022, it raised $4M in pre-seed funding in 2024 as investors bet on AI reshaping the dating landscape. The platform has recorded 1.5M sign-ups. Its pitch deck reports that 10% of beta dates resulted in marriage. Keeper builds profiles from extensive personal data, including test scores, finances, photos, and personality assessments, and uses a mix of traditional algorithms, custom LLMs trained with Stanford researchers, and human matchmakers to narrow candidates.

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Apple Is Cracking Down on Viral ‘Tea’ Apps, Citing Persistent Privacy Concerns

Posted on October 23, 2025
Tea app

BUSINESS INSIDER – Apple has removed the Tea and TeaOnHer apps from the App Store after ongoing privacy and moderation issues. The anonymous dating review apps faced backlash following major data breaches that exposed users’ selfies, IDs, and messages. Despite Apple’s repeated warnings, the developers failed to meet safety standards. TeaOnHer’s founder said his team added AI filters and anti-bullying tools but called Apple’s decision disappointing.

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Amata Is a New AI Matchmaker

Posted on September 30, 2025
Amata app logo

BUSINESS INSIDER – Amata is a new dating app rolling out in New York that swaps swiping for an AI matchmaker, which proposes a date and handles the planning; DMs only open two hours before meeting. Users pay a $16 per match (with plans to raise the price), can bank the token if a date cancels, and repeat cancelers get a 7-day pause. The company raised $6M pre-seed and learns from post-date feedback to improve matching. Its founder, Ludovic Huraux, previously built Attractive World and Shapr.

See full article at Business Insider

Gigi Pivots From AI Dating App to LinkedIn Rival

Posted on September 24, 2025
Logo of Gigi

BUSINESS INSIDER – Clara Gold shut down her dating app and relaunched Gigi as an AI-powered professional network that uses calendar data to map real relationships and prompt warm introductions. An invite-only beta went live in Sep 2025 across the US and Europe, with broader expansion planned for 2026. Gigi raised $3M led by Khosla Ventures, bringing total funding to $8M, with other investors including Sequoia, OpenAI, and Monashees. The pivot reflects dating apps’ retention problem and Gold’s view that LinkedIn connections often lack real strength; Gigi targets relevance by recommending who to meet and when, in exchange for deeper data access.

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12 Startups Raising Millions to Disrupt Dating Apps and Social Networks

Posted on September 18, 2025
Startups Raising Millions to Disrupt Dating Apps and Social Networks

BUSINESS INSIDER – Business Insider reviewed pitch decks from 12 startups disrupting dating apps and social networking, many tackling loneliness, dating fatigue, and dissatisfaction with incumbents. Investors are backing both Big Tech alumni (e.g., Retro, PamPam) and Gen Z founders (e.g., Kndrd, Noplace). Notable raises include Posh ($22M Series A), Spoon Radio ($17M), Clyx ($14M), Pie ($11.5M), and Meet5 ($9M). Seed rounds went to apps like Hangout ($8.2M) and First Round’s On Me ($3M), while Series, an AI professional network for students, raised $3.1M pre-seed. Some startups are experimenting with freemium models or user-backed funding, but investors caution that not all are venture-scale.

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Bumble’s CEO Isn’t Giving up on Helping People Make New Friends

Posted on August 7, 2025

Bumble For Friends
BUSINESS INSIDER – Bumble will launch a new version of its friend-making app, Bumble For Friends. It's a "long-term growth" opportunity for the company…as demand for friendship, real-world connection, and belonging continues to grow." BFF is built on Geneva, a community platform Bumble acquired ($17m in July '24). One-on-one matching, IRL events, and community features are included. Friend-making apps have been having a moment, too. IRL apps 222, Pie, and Timeleft are setting people up with strangers or connecting them with local communities. Bumble reported a 7.6% YOY Q2 decline in revenue, decreasing from $269M in 2024 to $248M. Paying users declined 8.7%.

See full article at Business Insider

Mark Brooks: Bumble is beautifully positioned to be social, but the path is fraught with danger. Dating and social are antithetical. However, I think Bumble, under Whitney, can pull this off.

Curated by the Courtland Brooks team