Dear Love Doctor

How Do I Prevent A Stopover Date?

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


I recently left the island for a vacation, where I met a middle-aged gentleman who’s also from Jamaica but miles away in Ochi.

We spent four days on vacation chatting away and flirting, we didn’t hold hands or move on romantically.

We exchanged cell phone numbers before I flew back. That was two weeks ago and he had ignored me until yesterday. His message said that he would like to meet up in early April in Kingston.


I’ve yet to respond. I really like this man but I don’t want him thinking that he can stop over.

Rita, Kingston


Love Doctor’s Answer:

Love Doctor Monti and his Criss Ting

The fact that he’s finally been the man and made contact speaks volumes, and means that he is making an effort by suggesting a visit to Kingston.

Ocho Rios is only around an hour away by car, so there’s no reason that he should get overly amorous and expect a dirty stopover with you when there was nothing more than chatting and flirting. You really don’t need to overthink his gesture to visit you in Kingston.

My advice is to suggest a lunchtime rendezvous with him in Kingston, maybe somewhere classy and relaxing like Bath Fountain Hotel & Spa or the Pegasus Hotel.

You can even boldly suggest that he brings his swimwear as the outdoor pool at the Pegasus is impressive, and cheekily flirt by referring to your vacation (assuming that you went on a beach break).

I suggest that you make plans with some galpals for late on Saturday night, so it gives you an excuse to disappear after 9pm and he gets the message that he should return to his own bed.


As he only lives 80km away then he’s bound to have seen most of the sights of Kingston. However, do ask him if there’s anywhere special in the bustling city that he would like to visit. It’s pretty romantic going on the Kingston Blue Mountains Tour with coffee tasting.

Remember that he’s coming to see you rather than go around the city, and that you don’t really want to spend so long together that you feel he will want to stop over. You just wish to try and impress him.

There’s plenty of idyllic places to spend time together such as Devon House, Emancipation Park, Holywell Park and Lime Cay.

As you profess to liking this man romantically, treat this get together as your first proper date. In fact you even tell this love interest that you are looking forward to your first proper date.

Once he is armed with this information he may up the ante and become chivalrous by pulling out all the stops for your first date.

If he reacts positively about this being your initial date, as the previous encounters were only on vacation, then he should be the man and suggest where to meet and discuss an itinerary. This is when you can inform him you have plans from 9pm.

The scenario is very different to a typical first date as you’ve both probably revealed quite a lot about yourselves. If he considers this to be a date, now knowing quite a bit about you, then he’s obviously interested in you romantically.

Just bear in mind that you don’t want to say the same things that were mentioned on vacation, especially any funny stories, so aim for some conversation starters.

To maintain some genuine interest between you, consider the information that you’ve already been given. I suggest researching some of his interests/hobbies, so that you can bring these into conversation. Having a mutual interest is the glue that can hold a couple together during the early days of courting.


If you’ve forgotten what his hobbies are then you should try looking him up on social media, but obviously don’t ever inform him that you checked out his profile.

Your best bet, once you’ve sorted out a date to meet up again, is to prepare yourself both mentally and physically.

Mentally you can try visual tricks to reiterate to yourself that the rendezvous will run smoothly. When you have some spare time, try to envisage where you will go, what you will wear and what genuine compliments you wish to dish out. By undertaking these visualisations, when it comes to your date you won’t feel nervous.

Physically you need to make the best of yourself in order to impress him. Work your way from top to bottom with an improved grooming regime. As part of your grooming overhaul, I suggest that you invest in some good scent. You’ve probably got lots, but by getting a new one it will instil confidence and this can become your signature smell for this potential beau.

During the date don’t forget to inform him that you’ve already got plans with galpals from 9pm onwards.

Although he’ll probably be disappointed, if you want to move things along romantically for future dates then give him some clear-cut signals. A playful touch and locking eyes a little longer than you do with friends are terrific ways to flirt. The best signal, now that you know each other reasonably well, is to start talking about doing certain things together in the future.

When it comes to closing out this date and going off with your friends, I urge you to let him know that you had a great time and try to set up another date. The thrill of the chase is particularly exciting and rewarding for men, so more than likely a second proper date can be arranged.

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