National Matchmaker Day: Expert tips for setting up friends like a pro
Published: August 31, 2026 at 3:23 PM
HOUSTON – It’s National Matchmaker Day — a day to celebrate the people who have been playing Cupid long before dating apps made finding a connection just a swipe away
Maybe you’ve looked at two people you know and thought, “You two would be great together!” If so, you may already have the instincts of a matchmaker
But what actually makes two people a good match? And how do you make introductions without making things awkward?
Connection expert Jenn Pinkerton has some answers. A psychotherapist, speaker and high-performance coach, Pinkerton specializes in relationships, attachment, intimacy and communication
Here are some of her tips for becoming a better matchmaker:
- Look beyond shared hobbies. Two people don’t have to love the same activities. Shared values, lifestyles and even energy levels can be better indicators of compatibility.
- Think about the bigger picture. Consider whether they want similar things when it comes to relationships, family, finances, socializing and downtime.
- Ask both people first. Give them the choice to decide whether they’re open to meeting someone rather than putting them on the spot.
- Don’t oversell the match. Skip the “They’re perfect for you!” pitch. Instead, share why you think they might connect and let them form their own opinions.
- Let the connection happen naturally. Your job is to create an opportunity — not manage the relationship. Once you’ve made the connection, give them space to see where it goes.
- The best matchmakers aren’t focused on controlling the outcome. They notice a potential connection, open the door and let the two people take it from there.
Watch the full conversation with Jenn Pinkerton in the video above
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