Monday 18 December 2017

Michael English advises: I fancy my attractive older boss

Library Image. Dmitriy Melnikov ©
Library Image. Dmitriy Melnikov ©

Michael English

I'm 24 and have just moved to Dublin from the country to start a new job with a big firm. My manager is a very attractive older woman in her early 40s and she has been very nice to me since I started.

She has brought me back a cappuccino from the canteen a few times, and passed on free tickets for a concert.

She also pays a lot of attention to my work, and is always coming down to my desk, leaning over my shoulder to look at my screen and touching my arm as she talks to me. It's a fairly casual office, but I don't think she acts that way with the other lads in our team.

I really like her, to be honest -- she knows how to have the craic and looks really well for her age.

I'm not an expert, but I think she might be interested in me too.

I'd like to ask her out for a pint, just the two of us, and see how we get on.

I've always loved the idea of being with an older woman, and she'd be ideal.

I'm thinking it might be a bit awkward if I'm wrong, though. I don't think I am, but what would be the best way to approach this?

Is there a way I could suss her out a bit more before I make a move?


Hi Alan.

First of all, I know what it's like to move away from home and make your own way in the world. It can often be a lonely place when you land in a big city until you find your feet.

I left home and started in the music business at the age of 17. I travelled lots for many years and still do, and I've made lots of friends along the way.

I know that without these good friends, I wouldn't be able to do what I do as they are always there at the end of the phone when I need them.

But sometimes, I suppose we can mistake good friends and the admiration they have for you -- whether it's in your workplace or your personal life -- for something completely different.

I'm not saying for a second that the vibes you're getting from this person are false, but I would tread lightly.

I know you said this lady is very nice to you by taking you some coffee and even giving you some concert tickets.

She sounds like a really nice person and someone anyone would love to have as their friend. But stop and think for a minute. Maybe this lady feels for you like a mother would feel for their child when they land in a completely new environment?

Perhaps she thinks you're alone in this brand-new set-up, and maybe she has been there in that same place when she was growing up?

I think if she had feelings for you, she wouldn't have just given you the tickets, but would have offered to take you to the concert with her.

Maybe I'm completely wrong, and I don't want to dash your hopes, but sit tight and don't rush into anything for the time being and see what unfolds.

In the meantime, I know it probably is difficult being in this totally new place, so why don't you join clubs and societies that interest you? This is a great way of meeting new people your own age and interacting with them.

When you do meet these new people, you'll be surprised at how quickly you'll become part of a new circle of friends.

If you're finding that you like this person at work more and more, why don't you wait until there is a work get-together and see how you get on?

I'm sure if she feels the same as you do, she will give you some inkling at an event outside of the office.

Personally, I don't think there's anything wrong with an age gap in a relationship, provided that each person has respect and cares for each other. I know plenty of people in such relationships who are very happy.

I also know people who are the same age where things just didn't work out, so I suppose there are no hard and fast rules.

All I can advise you to do is take things slowly, meet new friends and become familiar with your new surroundings.

Who knows, maybe this will all work out with this older lady and she will ask you out on a date? If this happens, go for it -- provided she's not married with five kids!

Best of luck, Michael.

Weekend Magazine

Promoted Links

Style Newsletter

Stay on top of the latest fashion, beauty and celeb gossip in our Style newsletter.

Promoted Links

Editors Choice

Also in this section