Dear Love Doctor

Spoiled For Choice, But Which Route Do I Take? Help Me Love Doctor

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

Next month is going to be exciting as I’m planning to go on my first blind date since my divorce. This has been lined up by my best friend, but since then a new guy at work has arrived and we are flirting on a daily basis.

I’m torn whether to bin my blind date, who sounds great, or be adventurous and take this flirting to the next stage with my colleague. What’s your view?

A, Kingston 5, Jamaica

Well they say that when you wait for a bus to come along that at least two arrive, and this analogy seems perfectly true in your case.


Love Doctor MontiA blind date set up by a bestie may sound promising, however your friend is going to have probably trod on the side of caution when selecting a potential beau for you following your divorce.

Bearing that in mind, this possible suitor is likely to tick many boxes for you, although the importance of you both finding a connection has yet to be tested. The build-up to this first blind date should be exhilarating, as expectations will be high and you are clearly out of practice.

Your best friend won’t want you to be emotionally hurt by your next date, so she is highly likely to have picked out a safety net guy with some trepidation just to get you back into the swing of things.

On the other hand, you need to be courageous on the dating scene. If this blind date becomes a loving, long-term relationship, or is just a one-off, then at least you are back out there dating.

Maybe the reason you are flirting with your new colleague is because you have discovered a new-found confidence as you have a date lined up. There’s bound to be a new spring in your step, and there is the fact that you are gradually preparing yourself for your first date.

This more confident you is obviously shining through in the workplace, and already you have become a head turner with this new guy.

Yet so much depends upon your particular roles at work as to whether it is actually appropriate, and indeed practical, to take your mutual daily flirting to the next level.


Such factors that will determine this is whether he is genuinely single, or whether he is just being playful. Would a full-on relationship jeopardise either of your positions at work? If one of you could one be in charge of the other person then how would the workplace management react?

When work colleagues date then, as long as their work doesn’t get affected, the management should be pleased. Happy people tend to be more productive.

Yet should this relationship come crashing down, the heartbroken couple need to concentrate on work. So many individuals throw themselves into work as a form of distraction to deal with a break-up. So again, the work management are going to be delighted with you both as individuals.

That was the good aspect. The main bad aspect of entering a romance at work is ultimately the gossip, which can spread like wildfire. The rumours surrounding you both can have a negative impact on the work environment, which can then ruin each of your long-term career plans.

As you are going to be new to the dating scene, following your trauma of going through a divorce, then of course you want your future romance to be a bed of roses.

Dating a new work colleague offers risks, such as how you would react should things not work out. However, he has definitely turned your head. To ensure that you don’t get hurt, I suggest that you simply be direct and ask him outright what his intentions are.

Maybe during a break at work you two could go for a coffee, then you can lay down your cards. Ask why he is just being flirty and nothing more.

You need to find out if you are giving off vibes, and whether this is just a sensual spark or could you develop into a loving partnership. Find out each other’s interests, to see if you could grow together romantically.

If you feel comfortable after your brief one-to-one with the new work guy, a romantic date seems the logical way forward so make sure that you arrange it.


I urge you to take matters of the heart slowly as you are only just bouncing back, so may not be emotionally ready for love and romance. This is why the blind date may be a better bet on a long-term basis.

You could, as long as you are not getting too serious, start dating the work guy and still go on your blind date. It wouldn’t be betrayal as long as you approached it as a one-off meeting with the blind date, and on top of that were not emotionally attached with the work guy by then.

At least you can discover which man is ideal for you. But please don’t carry on seeing two men, because that will cause problems and you would be unfair to both of them by offering false hopes.

Should you decide to date the new colleague and things are running smoothly, then you can always cancel your blind date. He may well meet someone before next month and cancel your blind date.

It is advisable above all else to ask your bestie who set up the blind date about the scenario. You may discover that your potential suitor is not that great for you, but he was being utilised to ease you back out there. Obviously don’t ask about this matter if your blind date is a relative of your friend.

Ultimately, the choice is yours. Weight up the pros and cons. Could a work romance really develop or is it just playful flirting? Is a blind date going to deliver you ‘the one’ that you desire?

You need to undertake some soul searching, and may well find that once you try a date then you simply aren’t ready for romance as your heart needs time to heal.

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