Dear Love Doctor

Can I Hit The Jackpot or Steer Clear?

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


I’ve been single for virtually a year. I met a dreamy guy I liked in town. We chatted and swapped numbers.

I asked around before I will ever make contact with him. Apparently he had a horrible break-up with his last girlfriend, it ended up in big fights. I don’t know the full story. I’m very religious and my family would frown upon a man who mistreats his woman.

I’m wondering whether to send a message or leave it. He’s not contacted me since. I’ve not seen him around. It could be the start of a big romance or it could be a disaster. What do you think?


Stephanie, Ocho Rios


Love Doctor’s Answer:

Love Doctor Monti and his Criss Ting

When a chance meeting occurs and there’s an instant attraction then it’s common to exchange numbers.

My advice is for any female to always be wary, and just take the man’s number. If he respects you then that’s going to be cool with him, should he get angry then walk away because it is his loss.

Should you give out your number next time, leave off the last digit. If the man is genuinely keen on you then he will add zero, one, two and so forth at the end until he finds you. If he goes to that much trouble at the start, then you can expect lots of attention from any potential beau.

Although there was an exchange of numbers, and you refer to him as dreamy, there was only a physical connection. Next is to peel off the layers to discover each other’s characters and dreams.

At least by undertaking some research you’ve learned that if you two date it may not be a bed of roses.

Innocent until proven guilty is how you should treat him, because you never know the ins and outs of his previous relationship. Maybe you can quiz him on a second or third date by asking him directly why his last romance ended.


Beware if he starts moaning in a bad way about his ex, and then gets nasty about any other former girlfriends. This reaction will strongly indicate he is a man who clearly doesn’t respect women.

Your family shouldn’t be dismissive of who you date, unless it is someone that really has caused immense problems. They are only being protective because they love you, but already you are talking yourself out of a potential date let alone a romance.

If you think that it will end in tears, for whatever reason, then steer clear of any form of contact. It sounds like it is a non-starter for him because he hasn’t been in touch. Although there may be a valid excuse, such as losing your number.

There are a plethora of ways to meet single men with ease, so you don’t have to just try to date him because you haven’t any other admirers.

As he is on your mind, but you’re treading with trepidation, my advice is to ask a close friend if she would be interested in a double date. That way you will feel safer with your galpal and her boyfriend near you on a first date.

It’s unusual to kick off a possible romance with a double date, but as you are unsure about things this may be the best way forward. At least then you are giving this man a chance.

You can also ask for feedback from your friend and her partner, with the all important question posed to them of whether they think your parents will like him.

A first date is always going to be a nervous scenario for both parties, as it is going into the unknown. I suggest having a keyword to go to the toilet with your galpal and then disappear to discuss this man. Women seem to love to powder their nose together for a bit of gossip, so it won’t seem an odd thing to do. It leaves the guys together to chat.

At least you aren’t sounding desperate, just because you’ve been single for some considerable time now. This man has turned your head and now it’s time to make a move if you really want to. Only you can determine this. If you remain in doubt then follow the adage of “If in doubt go without”.


Until you message or call him you won’t know if a date is on the cards. He could be feeling unwanted that you didn’t make contact, has not got your number any longer for some reason, he may have had second thoughts so lost interest or he might have met someone else.

You’ve got very little to lose, apart from time. I urge you to make contact with him if you remain interested in a date. Keep it short and sweet. Offer him two options of when you can meet, and don’t act too keen to see him.

This could be the start of a budding romance, or it could fall flat as a pancake with no date taking place.

If you initiate a first date, be aware that it should never be used as the litmus test. Both parties will be super nervous and just a few things are discovered, otherwise it becomes like an intimate job interview.

The next date, and there are ways to land a second date, is when you can learn more about each other. Finding a mutual interest is the key to moving forwards, and having similar aspirations greatly helps.

It’s up to you to seize the moment, you can always end things if he is actually a bad boy. Yet fate has paved the way for you to make progress on your journey to find love and romance, so take a gamble and here’s hoping it pays dividends. You may have hit the jackpot this time.

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