AI Won’t Fix Dating—But It Can Teach Us How to Date Better

AI and dating seem like a match made in heaven. If we could just know who you really are, then use a mega-computer to find your perfect person, everything else would take care of itself. Hence the rise of AI matchmaking, AI profile writing, AI text writing. Whitney Wolfe Herd, the founder of Bumble, even mused that someday our AIs might date each other.

In my experience as a dating coach and matchmaker, I believe that these investments in improving matching may lead to better matches—but they won’t lead to better relationships. The problem in dating isn’t just the algorithm. It’s everything else that happens before and after.

1. Mindset

People aren’t really open to each other. They protect themselves from disappointment with impossibly unrealistic checklists, hiding behind “high standards” as an excuse not to meet anyone. Underneath that, there’s fear—of rejection, of being seen, of being wrong.

2. Text Communication

Even with the right match, getting to the date isn’t obvious. Many people don’t know how to text effectively. Some meander and never get to the point. Others rush to the first date without vetting for compatibility. Post-date texting is equally confusing: a misplaced comma or a delayed reply can shift the entire meaning. People are both too sensitive and not sensitive enough.

3. In-Person Skills

After years of screens, people have forgotten how to date in real life. They turn first dates into job interviews, asking about career goals and attachment styles instead of really getting to know their date. Knowing how to end the date is also critically important - without this skill the first date can turn into a four-hour marathon that drains enthusiasm and accelerates burnout.

4. What Happens Next

Even when there’s a spark, most people don’t know how to pace the connection. They psych themselves out of something promising or move too fast because they’ve been told to “just be honest” or “go with the flow.” There’s almost no practical guidance for what dating looks like between the first and tenth date.

The Real Opportunity for AI

These problems are solvable—but not by generating better matches. The real opportunity is to use technology to teach people how to date better.

Step 1: Teach people how to text and date.
When text conversations stretch for weeks and first dates drag for hours, dating becomes a drain. In my coaching practice, I use a texting framework that helps clients do two things:
(a) determine quickly if there’s potential for a good first date, and
(b) get to that date within a week of matching.

Step 2: Teach people how to run their first dates.
First dates should last less than an hour and happen close to home or work. If it’s going well, great—still an hour. If it’s not, you know how to end it gracefully. When dating “costs” less—less time, energy, and money—people show up more willingly and more often.

Where AI and VR Come In

This is where I see the real potential for technology—not in matching, but in getting better at dating.

In my practice, I combine human coaching with AI and VR teaching tools. Real coaching is irreplaceable; I need to know my client, challenge their fixed ideas, and teach them how to communicate authentically. But once we’ve identified what they need to work on, the technology becomes a powerful extension of the process.

I use AI-based texting simulations to help clients practice how to move a match from chat to date naturally—how to keep tone, timing, and curiosity balanced.
Then, through VR practice sessions, clients rehearse real-life dating moments: how to start a conversation, navigate awkward pauses, flirt with confidence, or even end a date kindly.

After each session, the system measures conversational flow, empathy, and engagement. These aren’t “scores”—they’re diagnostic tools that help us see progress over time.

The Future of Dating Isn’t More Matches. It’s Better Daters.

In order to solve today's dating app burnout crisis we need to teach people how to date better. Dating is a skill and developing expertise takes practice. AI and VR have the potential to give people a way to get better.