Dear Jane,

I’m 28 years old and, although I’ve been actively going on dates since I moved to New York six years ago, I’m painfully single.

I’ve tried everything — dating apps, matchmaking events, blind dates and even run clubs — but nothing has stuck.

Over the past few weeks, I have been seeing a guy I met at a coffee shop, and things have been going pretty well. 

For whatever reason, my job never came up as a topic on the first few dates because we were so busy talking about other things. 

During our latest dinner date, the subject of our jobs finally came up. He mentioned that he works as a software engineer, and I shared that I am the personal assistant to the CEO of a prominent tech firm.

The atmosphere changed instantly, and the rest of the dinner felt uncomfortable. When it was time to pay, I offered to go halfsies, like I usually do. Normally, he would insist on covering the cost, but this time, he agreed to split the bill.

I texted him afterwards to thank him for a good date and he still hasn’t responded a week later.

Dear Jane: Every time I tell a man what my real job is, he dumps me. Will I ever find a man who can handle my career?

The change was apparent after I talked about my job, leading me to question whether other guys have also lost interest after learning about my work.

The CEO I work for is a public figure, he’s very handsome, successful and a billionaire.

I’m now wondering if the men I’ve dated think less of me because I’m the assistant to such a hotshot businessman. Maybe they feel threatened by his success, or maybe they assume I’m hooking up with him.

Looking back, no boy I’ve dated has ever reacted enthusiastically when I tell them about my work — but I always thought it was just because I have a boring job. Now I’m wondering if my career is an ick, or an instant turn-off to men.

I fear my job is preventing me from finding ‘the one’ and I don’t know what to do. Shall I quit?

From,

Professional ick

International best-selling author Jane Green offers sage advice on readers’ most burning issues in her agony aunt column

Dear Professional ick,

I can see why it must feel like there is a pattern here, and I also understand why you’re jumping to conclusions.

However, it’s very clear to me that anyone who is intimidated by someone you work for is not the man for you.

Who knows what your future holds, or who you might be working for – or with – as you progress in your career. 

But what I do know is that a man who isn’t immediately curious about your work – and who seems jealous of your employer – is showing glaring signs of insecurity. 

Rather than changing to make yourself more palatable to the men you date, you need to reverse your thinking: live the life you want to, and trust that the right man will be delighted just to be a part of it. 

The right man won’t be intimidated or threatened. In fact, he’ll be enormously proud of you.

Women too often try and change themselves to fit into someone else’s narrative. We make ourselves smaller, quieter or less impressive so as not to damage another person’s fragile ego. There are lots of awful men out there that make us feel the need to do this, but I can promise you, there are also some good ones, too.

Become discerning about who you date: make a list of all the qualities you want in a man and know what you deserve. 

Above all else, focus on building your own sense of worth, whether that’s through therapy, self-help books or online coaches.

Dear Jane,

I recently moved to Chicago for work, but I’m only here for a few months, so I’m subletting an apartment I found through mutual friends.

It’s a two-bedroom apartment, and the other boy living there is a friend of a friend — he is also the ex-boyfriend of my friend’s best friend, but I had never previously met him.

From the very first time I laid eyes on him, as he helped me haul my suitcases up the stairs to the apartment we would share, I was attracted to him. And the attraction only grew from there.

He insisted on showing me around the city, so I spent almost the entire first weekend I lived here hanging out with him.

From then on, we spent almost all our spare time together. He introduced me to his friends, and we almost always cook dinner and watch TV together — all the while, I’ve been developing a huge crush on him, and I have no idea if he feels the same way about me.

I’m now in an awkward position. I really like this boy — but I have to live with him for the next few months, and he’s the ex-boyfriend of a close friend’s friend.

I definitely don’t want things to get messy, but I feel as though we could be great together, and I don’t want to regret not confessing my true feelings.

Should I tell him I like him, or bury my feelings for the sake of peaceful living?

From,

Roommate romance

Dear Roommate romance,

A crush is the sweetest thing imaginable – but it comes with problems. 

When you have a crush on someone, it’s easy to start reading into it every single thing they do – interpreting each little look or comment as a sign that they might like you, too.

This is certainly not to say that your roommate doesn’t reciprocate your feelings, but in my experience, most men tend to be more explicit when they like someone.

But, of course, that is not always the case. Perhaps he is just shy or scared to confess his feelings for the same reasons as you. 

I can definitely relate to the uncertainty that often goes hand in hand with having a crush. When I was in my early twenties, I had a male best friend whom I developed an enormous crush on. 

We lived around the corner from one another, and I spent most evenings with him. We were both single, he was a great cook, we went to endless gigs, parties and concerts together. I was falling head over heels. 

We even went on holiday together, and I was convinced that not only would we make a great couple, but that he was surely harboring secret feelings for me. Why else was he spending so much time with me?

Eventually, I confessed my feelings… and it changed the friendship completely. 

He didn’t feel the same way about me, and for a while there were no more cozy dinners or fun outings. 

He quickly met a wonderful woman, and years later, they are some of my closest friends – and he and I still go to gigs and parties together when we are in the same town.

All this to say, things always change when one person confesses that they have romantic feelings for a friend. And, given that you are sharing an apartment, I would advise a more gentle approach. 

Perhaps initiate a conversation about romance – about who he might like or whether he has a crush on anyone. 

Really listen to what he tells you, and give him the opportunity to fess up, if he indeed does have anything to reveal. If he does not tell you that he has feelings for you, keep your own crush quiet. Appreciate him as a lovely man, a lovely roommate and a lovely friend.