How can I tell my boss I have feelings for him before I leave the country?

9 May 2022

Anonymous asks:

I have feelings for my boss. I’m 30 and he’s around 15 years older than me so I’m not sure if he sees me in a romantic way, but I do feel we have a strong connection. I’ve been through some difficult times during my time at the company and he’s emotionally supported me. He’s very respectful and as a HR Director he’s very aware of how to act so I think even if he felt the same way he’d be careful not to show it or act on it in case of crossing a line or making me feel uncomfortable. However I’ve felt a connection since I first met him. I’ll be leaving the company in 2 weeks time and moving back to my home country to start a new role. Since I’m leaving I want to subtly let him know how I feel and I know he plans to take me to lunch on one of the days during my last week. How can I test if he likes me without making a fool of myself and being too obvious? He’s unlikely to have any influence over my future career but we’ve developed a sort of friendship (within professional boundaries) and have agreed to stay in touch so I wouldn’t want to taint his impression of me as a professional or come across as desperate.

Karen Mooney says: Your boss sounds like a lovely, kind, caring man with very professional work ethics. You say he is older than you, if he is very much older that you, he may well have supported you in the past when you had some challenging times thinking of himself as a father figure. Think back to the times he has supported you, and what did he say to you and exactly how did he support you? This could be really quite revealing. Did he support you emotionally on a personal level or did he support you on a work-based level focusing solely on your happiness at work? If he supported you on a personal level this could show he has feelings for you, whether romantically or as a friend. You need to find out which one of these it is.

Igor Stevanovic / Alamy Stock Photo

You also say you will be returning to your home country, as you were in a strange country he could also have wanted to help and support you because he is a caring person, and you were far away from home. Ask him about his friends and his family life, try to get an insight of the man behind your boss. Ask him what he wants to do in the future, how does he spend his spare time. This will also tell you more. These are the type of questions a friend would ask.

My advice to you is to wait until you have lunch with him and say something in a lighthearted way, which gives him the opportunity to let you know if he has feelings for you. Something like “If you hadn’t been my boss, I think we could have been really good friends if not more…….”

You will not come across as desperate, I promise.

I hope this works. You must do something otherwise you will, leave the UK, never knowing what might have been.

Good luck

Karen Mooney is the Founder and CEO of Sara Eden Introductions which she started in 1988 after one too many friends had complained to her about their difficulty in finding a partner.

At the time she was working for the Royalty and Diplomatic Protection Department at Buckingham Palace. With the name ‘Sara’ meaning Princess and ‘Eden’ meaning paradise and love, it was with a nod to the past that she started on a future that has seen her become the UK’s leading matchmaker and relationship expert.

Over the past 33 years Karen has been responsible for literally thousands of marriages and long-term relationships.

She has been featured in a host of magazine articles and on numerous TV and radio shows.

A forthright and funny blonde, she pulls no punches when it comes to expressing her opinions.

Karen's clients are successful professionals and retired professionals ranging in age up the late 80’s. The level of membership she personally looks after has an amazing 95% success rate.

Her days are spent handling people with tact and diplomacy, dealing with their relationship problems and finding them a partner for life. She becomes her clients' confidante and trusted adviser.

Her attitude to matching is simple, "'We do what families used to do 100 years ago" says Karen "Then, they used their contacts to find a good match for their daughters, like in a Jane Austen book. We do the same thing; we use our extensive database. People don't have to settle for Mr or Miss Second Best nowadays."

Her clients include a host of well-known media personalities, although, understandably, she is the soul of discretion when it comes to revealing their names.