Is Career Risk Too Great For Dating The Boss’s Daughter?

If you fancy sending your romantic relationship dilemma to former Kingston resident Love Doctor Monti, author of Journey To Find The Perfect Partner Forever, submit your question via our form.

Alternatively send a direct email to [email protected] or via WhatsApp to +385 97 655 8066.

Love Doctor Monti is academically trained in interpersonal relationships, partnership intimacy and psychologically.

Question:

I’ve been admiring from afar the single lady who last year joined the company where I work. The problem is that she is the boss’s daughter, and we’ve only exchanged words a handful of times.

She is at least 10 years younger than me, and much flashier. She wears expensive perfumes and clothes plus drives an upscale car.

My heart somersaults every time I see her, although I don’t know if she even knows my name. I realise that I will become the laughing stock at work if I get rejected for a date, is it worth a shot with this gorgeous woman?

W, Kingston

Love Doctor’s Answer:
 
Although I admire your bravado, there are a plethora of potentially negative outcomes should you approach this lady for a date.

Although you find her so attractive that your heart beats faster each time you see her, you could find this vision of beauty unattainable.

My advice is to initially work out your value to her, and I’m not referring to financially. You should calculate what you could offer her in terms of both a short-term and long-term basis.

Although she has all the trappings of wealth by sporting expensive attire and scent as well as driving a flashy car, these are just materialistic things and don’t represent guaranteed happiness.

A caring and considerate nature is an essential element you require, because it sounds like she has been showered with the finer things in life. Frequently, rich parents will attempt to buy the love and affection with gifts.

Ultimately she will be seeking someone who she can admire, have similar aspirations, enjoy fun times together with mutual respect and understanding. There also needs to be chemistry and passion.

BE TRUE TO YOURSELF
However, you don’t want to change your personality just to try and date this lady. You can up the ante on the way you look and smell, but do maintain your unique personality.

Her initial thought, should you ask her for a date, will be whether a relationship with a colleague is both appropriate and workable as there are a plethora of obstacles.  If she has a much higher status at the company then this makes it tricky for you, because she’s bound to be ambitious and won’t wish to be seeing someone who is on a much lower rung than her.

There’s also the significant age gap to consider. In certain cultures, such as Russia, it is expected for a man to date someone young enough to be their daughter. Yet you are in Jamaica, and this could be frowned upon if there’s at least a 20-year gap.

My rule of thumb for any age gap in a romantic relationship is 13 years, although if the couple are true soulmates then this figure can be much higher.

STAY WITHIN YOUR BUDGET
Before you consider asking this lady out, you should figure where you could take on dates and whether you could afford to on a regular basis. You don’t want to be stretching yourself financially just to meet and try to impress her.

Women tend to question why a man would be interested in her. They can assume there’s something wrong with him to be currently single, and if he’s already married or seeing someone then he can’t be trusted. If he picks her, rather than she chooses him, then what are his intentions?

The majority of men, being highly visual creatures, are only attracted to younger ladies who are considered to be beautiful by virtually everyone. These sort of males are generally only interested in fun and frolics, which makes them selfish people because they aren’t actually considering the lady’s feelings.

You have to start scratching below the surface to find out about this women’s personality and hobbies, rather than simply have your head turned by her good looks and the fact that she’s considerably younger than you.

Having similar interests is a perfect foundation for building up a romance. Therefore, I urge you to do some detective work about your love interest’s hobbies. Only if they align with yours should you consider organising an organic way to bump into her.

SET UP A ‘CHANCE MEETING’
When you do, you’ll discover whether she actually knows who you are. If she doesn’t then at least you can mention that you work in the same company and try to engage in conversation.

Your orchestrated ‘chance meeting’ is the perfect scenario to determine whether there could ever be a romantic connection between you.

Although she may initially appear dismissive, this is potentially your only window of opportunity outside work to make an impression by flirting.

As well as making the best of yourself appearance wise, you need to ensure that you undertake some eye-gazing (keep eye contact for two to three seconds), smile with your eyes and just blurt out short sentences that do not include the word I. When she replies do not interrupt, ensure that you nod your head to everything positive she states.

Should she wish to engage in a proper conversation, at the end then you can always tell her how much you enjoyed chatting and if she ever fancies a proper catch up that you know a great bar or cafe that you’ve been meaning to visit. She’ll either agree or shoot you down.

If she agrees, this will only a pre-date rendezvous. It is best to follow my guide on how to dress for a date, so you’ll feel confident when meeting up.

SEIZE YOUR OPPORTUNITY
If you find this lady devilishly attractive, then there are bound to be other admirers at work. So strike while the iron is hot to try and get yourself noticed outside the working environment, to give yourself a fighting chance and stand out from the crowd.

The obvious potential pitfall should you start to date is if the relationship lasts less than a year, like most romances. Your position at work could become tricky with her, your work colleagues and her father.

A messy break-up could damage your standing at work, which could result in you seeking a new job elsewhere. Or your failed romance could become public entertainment for your work colleagues. Think carefully about how you could cope, because you should enjoy going to work.

At the moment this lady is just a fantasy for you, because she is potentially oblivious to your mere existence. Do some soul searching and consider whether it’s her power and position in the company or age and looks as to why you find her attractive.

Until you know more about her personality and hobbies, this lady with her wealthy lifestyle is unattainable. It’s crucial to find out if her character is compatible with you before you try to discover if she could fall for your charms.

Remember to share this article on Facebook and other Social Media Platforms. To submit your own articles or to advertise with us please send us an EMAIL at: [email protected]