Relationships

A Dating Expert Says You’re Probably ‘Over-icking’ Yourself Out of Love

Maggie Ekberg
June 11, 2026
Why Modern Dating Feels So Impossible, According to a Dating Expert
Image: Priscilla Du Preez 🇨🇦/Unsplash

If you’ve ever found yourself staring at your phone wondering why dating feels borderline impossible lately, Amy Chan has some news: it’s probably not bad luck. 

On The Wellness Process, host Elizabeth Endres sits down with the dating expert to get into all the sneaky ways modern dating trips us up, from how we pick people to why the spark fades right on cue. Most of it, Chan says, comes down to patterns we don’t even realize we’re repeating, which makes them a lot easier to change than you’d expect. 

Why Modern Dating Feels So Impossible, According to a Dating Expert

You might be ‘over-icking’ yourself out of love

Dating apps trained us to shop for people like a custom order. “The endless options cause us to assemble partners like Build-A-Bear,” Chan says, picking a height, an age, a vibe, until people stop feeling like people. Pair that with a feed where red-flag content always outperforms green-flag content, and you get a culture of bailing on someone over nothing before a connection has a chance to form.

The fix isn’t lowering your standards, it’s catching which way you lean. On one end is no standards at all, on the other is being so guarded you “dismiss people before they have a chance.” Both make a real connection impossible. As Chan puts it, you have to “know where you are on that spectrum and figure out how you can get back toward the center.”

Figure out where you get stuck in the ‘dating funnel’

Chan maps dating as a five-stage funnel: prospecting, discovery (dates one to two), evaluation (dates three to 20), commitment, and retention. The key insight is that people tend to get stuck in the same stage every single time.

Instead of declaring yourself bad at dating and giving up, you find your specific sticking point. “If I know you can’t go from discovery to evaluation, there’s only about five probable scenarios,” she says. “When we work on that, you convert and you keep going down the funnel.” Suddenly, it’s a fixable glitch, not a personality flaw.

Remember: the first two months don’t count

That giddy, can’t-stop-smiling high at the start of something? Chan says to take it with a grain of salt. “The first two months of dating don’t count. You are hopped up on love drugs, namely dopamine,” she explains. The problem is we treat that honeymoon rush like it’s the baseline, so when someone eventually levels out, we panic and start over-proving ourselves to win the high back.

This is the whole reason the evaluation stage matters, and why anxious daters especially can’t rush through it. “There’s no fast forward,” she says. You only really learn who someone is by giving it time, long after the dopamine wears off.

Know that the 18-month mark breaks people

Chan says 60 percent of breakups happen around the 18-month mark, and it’s not a coincidence; it’s chemistry. Your brain shifts from the dopamine-fueled passion stage into the calmer, oxytocin-driven companion stage.

The mistake is reading that calm as falling out of love. “They think that, ‘Oh my gosh, something is wrong. I don’t feel butterflies. I love you, but I’m not in love with you.’ And they break up with their partner,” she says, when really it’s just the natural evolution. The fix is novelty, what she calls relationship hygiene: try something new together, travel somewhere unfamiliar, stay genuinely curious about each other. “It doesn’t happen automatically.”

Listen to the full episode on The Wellness Process, available wherever you listen to podcasts.


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