He Liked My Ambition—Until He Didn’t: A True Story of Ambitious Women and Soft Men

A true story of mental health, ambitious women, and sensitive men.

---

By Jenny Smith Mattfeldt Published May 05, 2025

Names have been changed for privacy.

It started in December—one of those snowy, cinnamon-scented seasons where everything feels like it could be the beginning of a rom-com. Lola met Ryan in a way that felt promising: quiet car rides to see Christmas lights, side-by-side conversations that didn't require eye contact, just honesty and the hum of the road. They talked about everything. Her law school chaos. His paralegal job. Their mutual exhaustion with the system and their shared understanding of what this career path actually demands.

He got it. He got her. And for Lola, who usually kept people at arm's length, that meant something. He was soft-spoken, sweet, and he even knew her mom—so, sure. She let herself lean in a little.

Things started the way these things usually do: late-night texts, FaceTimes between case briefs, mutual support. He understood what it meant to spend twelve hours in the library and still feel behind. He understood the pressure, the panic, the need to prove yourself in a room full of people who look like they were born for the Supreme Court. It felt like a rare kind of comfort. Like being truly seen.

But fast forward a few months, and Lola is on my couch, sipping an espresso martini and asking one of those three-month-in questions every woman faces eventually: "How do you bring something up that’s bothering you without it blowing up the relationship?"

It’s the evolution every high-achieving, emotionally guarded woman goes through. Learning to communicate feelings you’ve spent years hiding. Giving voice to the things that hurt, instead of swallowing them. Taking the risk of being seen not just for your ambition, but your vulnerability.

So Lola brought it up.

She told him—gently—that it hurt when he disappeared for entire weekends without a text. That it worried her how much he was partying. She wasn’t accusatory. She wasn’t dramatic. She just... brought it up. Like women are told to do. Like he said he wanted her to do.

His response?

"I just get so anxious. I’m scared of upsetting you. I thought you’d be home more often. I don’t like that you’re away at school so much, it makes me feel disconnected."

Ah, yes. The modern soft boy’s greatest trick: ask for emotional honesty, then retreat into a shell

the moment you receive it. Say you have no issues in the relationship until she does, then rapid fire everything you can.

It didn’t stop there. At some point, he brought up that his family was concerned about her being on SSRIs. That maybe, they thought, she wasn’t really herself on them. As if managing anxiety in law school makes you less real. As if mental health support is something to whisper about in shame, instead of applaud. And then, the kicker—he asked if she would ever consider getting off of them.

(It also begged the question: why was her prescription being discussed at his family dinner table in the first place?)

Eventually, he called and ended things. Said he couldn’t handle the emotional weight of it all. And Lola, for all her ambition and toughness, was heartbroken... for a minute. But in the way that all wise women eventually do, she saw the humor. She saw the pattern.

And so did I.

Because here’s the thing: we’ve been told—finally, loudly, proudly—that it’s okay to be ambitious. That we can be strong, successful, career-driven women who still find love. But what if that’s only half true?

What if our ambition cuts our dating pool in half?

What if the kind of men who claim to love driven women... only love the idea of them?

We’re in an era where women are thriving more than ever. By 2030, two-thirds of the world’s wealth will be in women’s hands. We’re building empires, running courtrooms, saving lives. But in our personal lives? We're still being told to shrink. To be less sharp. Less sensitive. Less driven. Less much.

And the wildest part is—it’s not coming from the traditionally masculine types. It’s coming from the men who say all the right things. The ones who like your ambition, until it makes them feel small. Who ask for honesty, until it reflects something they don’t want to see. Who say they value emotional openness, right up until you express an emotion that inconveniences them.

We don’t need softer men to balance us out. We need stronger ones. Men solid enough in their own masculinity that they don’t feel threatened by ours. The kind of men who build you up not out of obligation, but out of confidence. Who don't shrink when you shine. Who want to see you win.

Lola doesn’t need a man to balance out her masculine energy. She needs one strong enough to let her rest in her feminine.

So if you see yourself in this story—if you’ve dated the man who loved your ambition until it asked something of him—maybe it’s time to step away from the boy who spirals over texts, and toward the man who’s too busy building a life to be afraid of yours.

---