Modern dating has become a strange little jungle. We have apps, profiles, screenshots, ghosting, group chat analysis and an entire generation trying to decide whether someone is emotionally available based on text speed. Somewhere along the way, dating started to feel less like connection and more like a strategy meeting nobody prepared for.
So “modern love” feels worth interrogating. What does it mean now? Is it meeting someone in the wild? Is it silently quitting the apps without deleting them? Is it admitting attraction is not enough when the character concerns are already waving from the sidelines?
Those questions shaped my conversation with Clay Harbor and Heather Norman ahead of Modern Love Unfiltered, Three Day Rule’s private Chicago event at Soho House. Harbor, the former NFL player many viewers know from The Bachelorette and Bachelor in Paradise, brings the perspective of someone who has dated privately and under national television pressure. Norman, a Three Day Rule matchmaker, brings more than a decade spent helping people stop treating apps like their only option.
Together, they made one thing clear: modern dating may not need more rules. It may need better questions. When asked what modern love means now, Norman said singles are not always loudly leaving dating apps. Some are doing something quieter.
“People are actually doing a little bit of quiet quitting from the apps,” Norman said. “They’re on there, but they’re not actually using them. We’ve seen a big shift to in-person events, to asking your friends to set you up and actually working with matchmakers.” Harbor, naturally, took us straight to the draft board.
“I would say it’s when you start chasing alignment instead of attention,” Harbor said. “Sometimes people are dating like they’re a bad NFL GM. You’re chasing the height, the speed, the strength, when you should be questioning those character concerns.”
That line works because it tells the truth. Sometimes the checklist is just chaos in a better outfit. The height, money, photos, lifestyle and perceived status can create the illusion of compatibility without answering the real question: Can this person actually build something with you?
Norman said her work often starts underneath those surface-level demands.
“It’s about going deeper,” Norman said. “What is the actual value you’re looking for? It’s actually not six feet tall. You might be looking for security. You might be looking for safety. How does that man provide that in another way, or how does he make you feel?”
Before matchmaking, Norman planned more than 550 weddings. She asked couples how they met, where they came from and what kept them connected. Over time, she saw patterns around compatibility and long-term partnership.
“I found a lot of trends in what created compatibility and long-term partnership,” Norman said. “From that, I transitioned over into this side of love, the other side of love, and helping people find that connection.”
Harbor understood the concept quickly. Matchmaking, to him, sounds a lot like football. Talent matters, but talent without direction can still look like a mess.
“The concept of matchmaking to me fits perfectly because it’s like you have a coach,” Harbor said. “Every great football team, you have the best players, but you’re only as good as your coach.” And yes, before anyone panics, Three Day Rule is not telling people to wait three business days before sending a text. In this dating climate, that is not mystery. That is how you get accused of ghosting before anyone even picks a restaurant. Norman said the name plays on the old dating rule, not the company’s actual advice.
“We do not suggest doing that,” Norman said. “We want people to just be genuine, authentic, be yourself, and that’s how you really can build a long-term lasting relationship.”
Harbor, who is now in a relationship, said dating changed as he matured. His younger years were less intentional, but time sharpened what he wanted. “I am more focused on getting to know someone and building something that is more intellectual than physical,” Harbor said. “When you start to mature in dating, you realize that’s the more important thing.”
His public dating experiences also taught him to be clearer. Harbor joked that he went from being judged by thousands on Sundays for football to being judged by even more people on Mondays through Bachelor Nation. Still, the lesson was useful: say what you want.
“I’ve learned over my dating experience just how being intentional and upfront and letting people know what your intentions are, what you’re looking for, what you want out of this is very important,” Harbor said.
Still, neither Harbor nor Norman believes people need to become perfect before dating. That idea sounds mature, but it can also become a very polished excuse to avoid being vulnerable. Heal, yes. Grow, absolutely. But waiting until every flaw disappears may keep people standing at the edge forever.
“There’s never a perfect time,” Norman said. “A lot of times people want to say, ‘Oh, I want to be completely ready before I step into this,’ but there’s so much growth that happens within a relationship and within dating. You don’t have to be perfectly ready before you start.”
Harbor agreed and brought it back to the field. “You’re still playing football and you’re getting better at football at the same time you’re getting stronger,” he said. “It all works together.”
When asked what makes someone most matchable, Norman said self-awareness matters, but so does openness. People should know their core values, but they also have to leave room for surprise. Translation: your type may not be the prize you think it is.
“I would say that somebody coming into the process, knowing their core values, knowing who they are and what really matters to them on a deeper level, but then also allowing yourself to be surprised,” Norman said. “Making sure that you’re dating a little bit outside your type.”
Harbor met his current girlfriend the old-fashioned way: at a bar in the West Loop during Halloween weekend. No app. No matchmaker. No dramatic rose ceremony. Just Chicago, chance and apparently enough nerve to say something.
When asked what makes a Chicago woman different, he pointed to Midwest values and local energy. “For me, it’s something about the Midwest,” Harbor said. “When you do meet people from the same area, you do kind of have this connection and you feel like you have something in common, and you kind of view things the same way.”
That feels about right. Chicago sits somewhere between calm and absolutely not. Friendly, but not foolish. Warm, but still watching. For people tired of dating, Norman does not suggest doubling down on whatever already feels draining. Instead, she said people should spend more time doing what makes them feel alive.
“Do things that you love,” Norman said. “Take a little bit less focus on the constant swiping and constantly forcing yourself to get into a habit that’s maybe draining you, and really spend your time doing things that you’re passionate about that you love.”
Her larger advice is even simpler: go outside, look up and give people an opening. “I would tell people to put themselves out there,” Norman said. “Go outside, look up from your phone, talk to the people around you, put yourself in situations that maybe you aren’t always as comfortable in.”
Harbor’s final advice was less about rules and more about releasing the pressure to find one perfect path. “Don’t worry about the right way,” Harbor said. “There’s no right way to do it. How you get there, it’s just about getting there.”
Maybe that is where modern dating keeps tripping people up. Everyone wants the perfect app, perfect person, perfect timing, perfect story and perfect explanation for why they are still single, dating again, trying again or taking a break. But love has never been that clean.
Sometimes it starts with a matchmaker. Sometimes it starts at a bar in the West Loop. Sometimes it starts because someone finally looks up from a phone long enough to notice who is standing there. Either way, the point is not to win dating. The point is to stop treating connection like a game nobody wants to admit they are playing.