Investors Inject $9.2m into AI Dating App Ditto for Yacht Blind Dates

By Dipo Olowookere

About 9.2 million funding round has been secured by an AI-dating app, Ditto, for the expansion of its iMessage-based matchmaker, with the participation of Peak XV Partners, Gradient, Scribble Ventures, Alumni Ventures, and Llama Venture.

The iMessage-based matchmaker plans real dates for users, handling everything from the match to logistics, so students can focus on showing up and connecting in real-life. Users grow tired of endless swiping and stalled conversations.

College students swipe endlessly, juggle multiple chats, and still struggle to turn matches into actual dates. Ditto was created to remove that friction entirely.

The business was established by two Berkeley undergraduates, Mr Allen Wang and Mr Eric Liu, who saw friends spend hours on dating apps without forming meaningful connections.

The platform initially launched at UC San Diego and went viral across sorority group chats before quickly expanding to UC Berkeley, USC, UCLA, and UC Davis.

It operates entirely over iMessage, where users already communicate daily. Users tell Ditto their preference for a date, such as ‘a 6 ‘2 hot nerd that brings me flowers’ or ‘an ABG who mastered leetcode’. After sharing their preferences and availability, users receive a text with a complete date plan, including the time, place, and details of their match, all centred around the campus they are near.

After each date, Ditto collects feedback and incorporates these feedbacks into the user’s profile to improve future matches. The result is a system that feels personal, efficient, and low-pressure, while removing much of the anxiety and inefficiency associated with modern dating apps.

“Our goal was to build something that actually helps people go on dates, not stay stuck in an app. When you remove swiping and chatting, you remove a lot of the toxicity and anxiety that people associate with online dating.

“We plan the date, people show up, and real connections have a chance to form. About 20 per cent of our matches turned into actual dates,” Mr Wang stated.

With this funding, Ditto is kicking off 2026 by hosting 10 yacht parties across the US, starting in Los Angeles on Valentine’s Day.

Each yacht will host 100 college singles, matched into 50 couples. This will be the biggest yacht party in college history. Ditto is co-hosting these parties with the hottest school clubs and Greek life organisations in Los Angeles, New York, Boston, and more.

A Partner at Gradient, Vig Sachidananda, while commenting on the new funding package, said, “Ditto is leveraging AI in a creative way to build a novel online dating experience — one which resembles a true matchmaking service.

“We’ve seen a great early response from users to this approach, and we’re excited to continue to work with Ditto as they expand to college campuses across the US.”

Since launching, Ditto has grown to more than 42,000 users across four college campuses, with over 25 per cent of users coming through referrals.

Looking ahead, Ditto plans to expand beyond college campuses and eventually support other forms of connection, including professional networking and group social experiences. The long-term vision is to become a matchmaker for modern life, helping people turn intent into meaningful, real-world interactions, one plan at a time.