How Do I Shake Things Up Because I’m Young, Desperate And Single? – Help Me Love Doctor

Why not send former Kingston-resident Love Doctor your relationship queries? Use the form to submit your question(s).

Love Doctor MontiQuestion

Valentine’s Day makes me think more than ever about being seriously single, made worse since socialising was restricted across the island last year. Every day is like groundhog day as far as lack of romance is concerned. How do I shake things up?

I admit I don’t know what I’m looking for but I’m almost 40 and live in Kingston, there has to be a girl out there for me in 2021. When will I find her?


Denzel – St Andrew

Love Doctor’s Answer

The fear of rejection can be discarded, to a certain extent, once a year with St. Valentine’s Day but the coronavirus crisis is dragging on and now the curfew has been lengthened then socialising is trickier than ever.

Groundhog day is exactly what it feels like, but Bill Murray’s character in the hit movie spent his days upsetting people and harming himself. He only escaped the drudgery of the daily loop he was stuck in when he showed love towards people. And that is exactly what you need to do to get out of your predicament of being single.

With traditional physical flirting – eye contact, handing out compliments, mirroring each other’s movements, reading body language, smiling, touching etc – out of the question, because people aren’t going out like they used to, means you need to be armoured with new weapons in the dating world. Namely small talk, showing your intentions, learning some compliments to deliver, polishing up your humour and self-improvement.

I would imagine that you have made contact with an ex-girlfriend or two as well as dipped your toe into the digital dating arena.

I suggest you prepare some small talk subjects that are common interests, but ensure you keep it light, for every lady that you’re trying to impress.

Body language normally gives the game away about whether there is a mutual spark, so by talking on the phone or online you must explain your intentions early on to ensure that you have the same or similar objectives as to where the potential relationship is heading.


Prepare some compliments that are bona fide just about her, not only will she realise that you have been thinking about her but by making her feel special will ensure that she will realise her worth from your carefully chosen words.

On the subject of words, dust down those lame jokes and come up with some new ones to inject some humour into her life. They say the way to a man’s heart is food and the way to a woman’s heart is a sense of humour. To give yourself a fighting chance you need to develop some jokes so that your love interest laughs, which will be a huge plus during this time of uncertainty.

Reaching the age of 40 is a major milestone in terms of romance, because it is generally when both genders believe that they are able to enter the last chance saloon. They tend to be desperate to settle down and have children.

Yet those aged 39 and 40 often stink of desperation, so there is usually disinterest from potential partners. Perhaps that has been your situation.

Jamaica is different to the rest of the globe because when a man has a love interest, the lady in question is oftentimes expected to like him back. He will ‘psst’ at a woman, yet even if she refuses to give him time of day he will pursue her and even insult her. Peer pressure has encouraged this attitude, even though it doesn’t occur the other way round with a lady liking a man.

As Jamaican men tend to believe that they deserve the most beautiful and sexy women to be theirs, there tends to be no reality check and too many men love to bun (cheat). If you are like this then maybe it is time to take a reality check and appreciate that your options are more limited during the pandemic.

Best bet is to spend this time to look at yourself to see how you can improve your chances in terms of attitude, lifestyle (a road terrorist pon di road or a stay at home guy?) and looks (consider a fresh haircut, new clothing etc).

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