Dear Love Doctor

Double Trouble, Which One Should I 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 bumped into an ex from years ago who wants to meet up as we are both single, and we have exchanged our new numbers.

A few days before this chance meeting, a family friend suggested that I meet a man for a one-off date. He looks like my type of beau.

I sort of would like to see this new potential suitor to discover if there’s a mutual connection. I don’t want my ex to know as he would be mortified.


Should I meet up with either of these men?

Jayden, Jamaica

Love Doctor’s Answer

In a way it is a good dilemma to have, as men obviously find you charming and attractive. However, it is wise to be cautious and so caring with this delicate situation.

Love Doctor MontiAt least you are not taking the bad attitude of having your cake and eating it, so well done for that.

You need to make a decision as to why you are so bothered about not wishing to hurt your former partner. Being protective towards him indicates that you still have deep-rooted feelings for him. Yet do you yearn to rekindle your relationship?

If the answer is yes, and you strongly believe that despite your past that you could make things work this time, then it seems illogical to entertain going on a blind date.

Many singletons would have been pushed into a one-off date just to make their ex jealous, but this is not the case with your scenario. The fact that you respect his feelings means that you could return to a loving relationship with him.


Before you dismiss this chance of a blind date, and remember that he could turn out to be ‘the one’, you should recall why you split up with your ex.

It is wonderful that there is no animosity between you, although the fact that you both have different numbers nowadays could have been the result of one of you being enamoured by the other even after you broke up.

I suggest that you make contact with your ex and be direct. Let him know that you were delighted to bump into him and would be happy to catch up over a drink, but don’t appear overzealous by offering to cook him a meal. The thrill of the chase is required to inject some excitement into your relationship blossoming once again.

You need to establish, before you meet up, his romantic status and also ask whether you are meeting as friends or has he got an interest in you. Once you have been courageous enough to find out his intentions, only then can you make a decision about whether you wish to pursue a blind date.

As you sort of wish to go out with a stranger, then your heart is not really in because of your ex.

The fact that your head has been turned by your former boyfriend strongly suggests that you believe he was the one that got away. However, he may not feel that way and maybe he was just being polite when you briefly saw each other.

Don’t get carried away by a fairytale finish with your ex, instead keep your feet firmly on the ground and ensure that you determine asap exactly how he feels about you.

There should definitely have been some chemistry when the two of you had a brief encounter. However, when you spend a considerable amount of time together then this may fade, alternatively the bond will grow stronger.

My advice is to get this established before you make a decision about the potential blind date. You sound considerate so won’t be dating both men, but you should give yourself a fighting chance on the journey of love and romance.


Your best bet is to know what is going on with your ex, and be honest with yourself about your true feelings. He may be flattered that you show a keen interest, but you are currently unaware of his emotional baggage whether from you and/or anyone else.

If it is going to be just a rendezvous as friends, or he no longer feels the same about you, then you should focus on the future by embracing this unexpected opportunity of a one-off date.

At least you can bide your time about setting up a blind date, and either let him down gently by explaining to your family friend that you are dating. Alternatively, try to give your ex another whirl and if that works out then you will live happily ever after.

But, as many people will no doubt have told you, it is always a dangerous game to play returning to a former partner. You broke up for a reason. In rare cases the status quo can return, with some couples finding their love for each deeper than the first time round.

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