Dear Love Doctor

How Do I Spark A Conversation For A Potential Date? Help Me Love Doctor

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


I’ve been single for too long and now I lack confidence. How do I approach someone single so that I can land a date?

Abigay, St. Andrew 

Love Doctor’s Answer:

Getting a date is a simple process, but landing a suitable date is more difficult. So my first piece of advice is to decide whether you want just any old date or whether you want more from life, and in this case a good quality date.


Love Doctor MontiThe secret to a good quality date is in finding some foundation to build a potential relationship. So if you can meet a single man that you find physically attractive, and he possesses at least one mutual interest, then at least he ticks the boxes.

There are so many ways to approach a man to spark a conversation, depending on the environment and interests. But the basics are to flash a genuine smile, show through positive language that you find him attractive and to ask his advice.

You can just ask a man for the time, for a lighter for your cigarette or even where they got their aftershave from because you couldn’t help noticing. With these three approaches you have shown an interest.

Once in conversation just take your time to build up a rapport. Show your interest by touching his arm whenever he makes you laugh, or you want to reiterate something positive that one of you said.

If you are too shy then the best bet is ideally to grab his eye by standing near him but only within his peripheral vision. However, do not reveal your entire face, just let him see your profile. Then slowly catch a glimpse of him every now and then, to give him a teaser of you. Those single men with confidence will smile or approach you, which makes life easier for you to get chatting.

Do not forget that lacking confidence is an unattractive trait. You need to improve your confidence otherwise many men could soon see that you lack self-esteem, which means that they could take advantage of you or they could lose interest in you.

Self confidence is a state of mind, which you must develop to improve. Whatever has happened in the past, even if your confidence was knocked by a silly comment from an ex-boyfriend, you now need to start afresh with a clean sheet.


Negative energy is a waste of energy is a Jamaican adage that you should employ, so visualise what you are aiming for overall and stick to maintaining a positive mindset.

When you feel good about yourself then you will gain immense confidence, which will inspire you to keep looking after yourself.

By concentrating on looking after yourself – such as dressing better, having a healthy diet, sticking to a good grooming regime, relaxing (listening to music, meditation or watching television etc), undertaking regular exercise – you will accept and recognise yourself as the person that you wish to be.

Once you start to appreciate yourself then others will too, which makes it simpler to find an emotional connection with a potential partner. Positive personality traits, including optimism and strong self-esteem, are going to make you more attractive overall.

Good looks alone are not enough to land a meaningful date, so don’t rely on simply making yourself look attractive because you really don’t want to be stuck with someone who is one dimensional.

Yet men are visual creatures, so they do initially need someone who is pleasing on the eye. Generally speaking, men are not as shallow as we are often portrayed and deep down want our special someone to possess good character.

Sweet romance can develop and move to that amazing experience of being lovey-dovey. The way it happens is that you need to let the relationship kick off with liking each other affectionately, move along to romance before the passion and intimacy arrives.

If you ever possess enough confidence then you can always go down the route of introducing chat-up lines. The majority of single men would be flattered to be chatted up by a pretty lady.

So much depends on the sort of potential partner you are seeking to be your leading man, but you may wish to turn your attention to a cultured man.


Maybe the reason you have yet to meet ‘the one’ is because you are a hopeless romantic, are too fussy, have been overthinking love and relationships, or are looking in the wrong places to meet a potential partner.

As a man’s best friend is perceived to be a dog, then if you want to grab some attention from a man organically I would urge you to consider borrowing a dog from a family member, friend or even a work colleague. In such a relaxed environment it should be easy enough to strike up a conversation with a stranger when furry friends take a liking to each other. You can approach a man to strike a conversation with ease in this situation.

However, you need to show the man that you are expressing a romantic interest in him by using positive body language rather than being forthright. Most men like to be the man in a relationship, so a woman who takes control can be off-putting. Do ensure that you let the man think he is in charge, even if you are manipulating the conversion.

The path of true love never runs smoothly, but you can get the ball rolling by briefly taking the lead if necessary when meeting a new man that you really like romantically.

The way forward is when you chat, try to mention some of your hobbies and interests to garner whether he likes any of these. If he does take the bait, then you can suggest doing the same activity together. Having a similar passion about something is a brilliant basis to build a relationship.

I suggest that for you to truly change things for the better you should seek a specific type of man to fulfil your romantic needs. Most singletons know what they don’t want, but rarely know what they do want apart from the basics of a suitable age range.

If you want to find a fulfilling romance then you need to visit the places where you can meet a viable suitor away from bars, clubs and dancehalls – where there is way too much competition.

Instead I suggest that you go to the places where you have a genuine passion and there will be singletons, whether it is an art gallery, sports club, swimming pool etc. You won’t be so nervous at these places because you feel happy in these environments, and it is easier to start a conversation as you will convey confidence as you have knowledge about these places.

If you are a hopeless romantic then you will be seeking a love interest who has Hollywood looks and only interested in enjoying a candlelit dinner.

Yet the reality factor needs to come into play, so that you don’t try to date those who are not on the same level as you either in terms of education, emotional baggage, finances, looks and so forth.


Once you realise what you can offer a relationship then it is best to ask some close friends if they know of any suitable single local men that they can introduce you to. You could be pleasantly surprised.

What you should seek is a long-term potential partner rather than just a date. A good indication at the start is when a man values the lady, so he gives her his undivided attention by genuinely listening.

A man who listens to you will surprise you after a few dates, such as remembering your favourite drink, holiday destination, scent etc. This type of man is a keeper and even if there is not an instant spark, I would suggest that you give someone like this time so that you can possibly develop a long-term loving partnership.

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