Sometimes, love feels like it’s hiding in the very city that’s supposed to be overflowing with options.
That’s how one woman is feeling after six years of dating in New York and coming up empty.
And now, she’s wondering if her career might actually be scaring men off before things even get started.
A Promising Date Turns Awkward Over One Topic
At 28, she’s done everything from swiping on apps to joining social events and even trying out running clubs just to meet someone special.
Finally, it seemed like things might be going somewhere with a guy she met in a coffee shop.
The conversations were flowing, the vibes were great — until their most recent dinner.
That night, they finally got around to talking about work.
He shared that he’s a software engineer, and she casually mentioned she’s the personal assistant to a high-profile tech CEO — a billionaire, no less, and very much in the public eye. The mood shifted immediately.
Suddenly, everything felt off. He agreed to split the bill (which he never did before), and after she texted to thank him later, he ghosted. It’s been a week — radio silence.
Is Her Boss the Real Problem?
Now, she’s spiraling. Has this been happening all along? She’s noticed that men never seem particularly enthusiastic when she brings up her job, but she always assumed it was just… boring.
But what if the real issue isn’t boredom — what if it’s intimidation? Is her boss’s success — and his looks — triggering some insecurity in the men she dates?
Could they be assuming something inappropriate is going on, or do they just feel overshadowed?
She’s starting to question whether being this close to power makes her seem like a threat — or worse, an “ick.”
Should She Quit for the Sake of Love?
Feeling defeated, she wonders if she needs to quit her job just to have a shot at finding someone.
But that idea? Jane Green, the voice behind the advice column, says absolutely not.
Jane’s Advice: Don’t Shrink Yourself for Small-Minded Men
Jane gets it — when you notice a pattern, it’s easy to blame yourself.
But in this case, Jane makes it clear: the issue isn’t the job, it’s the kind of man who feels insecure about it.
A confident partner will celebrate your success, not feel threatened by it.
A man who’s uncomfortable with your proximity to power is showing a major red flag — not of your worth, but of his own lack of self-esteem.
Rather than changing yourself to make these men feel more secure, Jane says it’s time to flip the script: build the life you love, and trust that the right person will be drawn to it — not scared off by it.
Build Your Worth, Don’t Bargain With It
Jane also reminds her — and all of us — that too often women shrink themselves to avoid bruising someone else’s ego.
But you shouldn’t have to dim your light just to get someone to stick around.
Instead, get clear on what you’re looking for in a partner.
Make that list, hold it close, and start being picky.
Therapy, books, podcasts — whatever it takes to reconnect with your own value, do it.
Because the right relationship won’t require you to trade ambition for affection.
When a Roommate Becomes a Crush in Disguise
Now let’s jump to Chicago, where a temporary work assignment has unexpectedly sparked a classic rom-com situation.
One woman moved into a new apartment for a few months — and found herself falling hard for her roommate.
From Carrying Luggage to Catching Feelings
She didn’t know him before moving in. He’s a friend of a friend, and the ex-boyfriend of someone in her extended circle.
But from the moment he helped her drag her suitcases upstairs, something clicked.
That first weekend, he insisted on showing her around the city.
Since then, they’ve spent nearly all their free time together — cooking, exploring, hanging out like a couple… only they’re not.
And she has no idea if he feels the same way.
To Confess or Not to Confess?
Now she’s stuck. Her crush is getting stronger by the day, but so are her concerns.
Is it worth the risk? What if things get awkward in their shared apartment? And what about that whole ex-of-a-friend situation?
She’s worried that if she says something and he doesn’t feel the same, it could ruin everything — not just the living arrangement, but the friendship too.
Jane’s Advice: Read the Room Before Making a Move
Jane totally understands the thrill — and the torment — of catching feelings for someone you see every day.
Crushes have a way of making us overanalyze every word and action, searching for signs that they might feel the same.
But Jane offers a word of caution. In her own experience, she once developed strong feelings for a close male friend, only to discover he didn’t feel the same.
Things got awkward, and the friendship shifted. They recovered eventually, but it was never quite the same.
Try a Softer Approach First
So, instead of a full-on confession, Jane suggests easing into it.
Start a casual conversation about dating or crushes — see where his head is at.
If he doesn’t mention liking you or hint at any romantic feelings, maybe keep your crush to yourself.
After all, not every connection needs to be romantic to be meaningful.
If he turns out to just be a great roommate and friend, that’s still a win — and it keeps the peace for the rest of your stay.
Jane’s Sunday Reminder: Choose the People Who Choose You
In both these situations — and so many others — Jane brings it back to this simple truth: we often settle when we don’t feel like we’re enough.
But when you truly love and value yourself, you’ll stop accepting crumbs and start expecting the whole cake.
Loving yourself doesn’t mean you won’t want companionship — it just means you won’t need it to feel whole.
Anyone who enters your life should add to the joy you already have, not complete a puzzle that was never missing pieces to begin with.