Dear Love Doctor

Should I Follow My Heart With A Lady I Only Just Met?

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


I recently got to know a stunning single girl, who is moving back to the island from Canada next year, for a few days. We got on brilliantly, swimming in the sea and just spending high quality time together.

I’m tickled to death because she’s career-minded, very good looking and has a sparkling personality. I’m just concerned that now she’s gone I’m suddenly having second thoughts.

Apart from her being nine years younger than me there were some red flags that included the fact that she drinks quite a lot and loves herself by constantly calling herself “hot”.


Should I pursue her and celebrate the potential of a romance blossoming, or wait for her to get back in touch? I’m so torn.

Sheldon, MoBay

Love Doctor MontiLove Doctor’s Answer:

Although it sounds like you enjoyed an amazing experience together, albeit briefly, you have already found flaws in her. My personal advice will always be “if in doubt go without”.

The course of true love never runs smoothly, but the blip should have been how to deal with the distance between the pair of you until she secures her move back to the island rather than your issue.

When romance starts, generally speaking we look beyond the obvious flaws and tend to brush them under the carpet. But that’s not a magic carpet where everything vanishes and couples live happily together for the rest of their lives.

The fact that you are having concerns already probably means one of four major factors. Maybe you have realised that she is not the perfect match that you so wanted. Or you simply need to find flaws so that you can move on guilt-free. Alternatively, you remain in love with another lady so won’t commit, or truly believe you’re such damaged goods that you don’t want to risk her getting involved and ultimately hurt.

Regardless of which of these apply, deep down this is all about self preservation to avoid heartache, pain and tears.


When you mention that she was drinking, don’t forget that she was on vacation so was only trying to chill. She may also have required some Dutch courage as you obviously turned her head, which she undoubtedly was not expecting.

Referring to herself as hot could have been because she was fishing for compliments from you, maybe she’s been single for a long time or is just plain insecure.

These two issues that are your red flags are easily outweighed by the lovely words you used to describe her as well as the time you spent together. You obviously had some sort of mutual attraction and connection.

You can’t rely on another lady to appear that will sweep you off your feet like this again, so you should trust your first and most natural instincts. I personally believe that you are scared that someone will take your place back in Canada.

When you state your query about pursuing her, then act smart otherwise she could break your heart. The more you chase the faster she could run, which appears to be what is the real issue here.

Be the man, be direct and simply send a message to her about how much you enjoyed your time together. Ensure everything is about her not you, so that she can appreciate that you care about her. The conversation needs to progress organically, with a natural ebb and flow.

I suggest you treat the conversation like a game of tennis, for example don’t ask her any questions until she asks you questions. 

The ability to get a romance blooming is always going to be worth celebrating, as only love and money really do make the world go round.

If she’s been silent since returning to Canada, then there’s a reason for this. She is probably catching up with work duties as well as family and friends.


Wait for a weekend before you contact her, as you’ve already mentioned that she’s career-focused. If you want her attention then get in touch when you believe she’s not at the office.

An exchange of affectionate messages will follow unless it becomes a one-sided love affair, in which case then you would be better off forgetting her. If you don’t gamble on a roll of the dice then you cannot possibly win.

This lady definitely has something that no one else has got in your eyes, which was the main reason why you wanted to spend time together. Yes, it was a spontaneous act and you both capitalised on being able to enjoy each other’s company.

Unless that was the wrong decision then there’s no reason to wallow or over analyse the scenario.

This isn’t the time to say goodbye to her. This is the perfect opportunity to learn more about each other without being intrusive. More importantly this is just the beginning of something that could turn into a loving long-term relationship.

Seize this beautiful moment and try to make it work so that you two can prove good for one another.

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