Dear Love Doctor

Should I Make The First Move?

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


I’m in spin about a new man I met in a cocktail bar with my galpal the other day. As we ordered the same rum-based drink we got chatting for a bit, and exchanged cell phone numbers.

I’ve not contacted him yet, because I don’t want to look too desperate. He hasn’t been in touch, which makes me worry that he already has someone in his life.

When should I cave in and make contact? Or should I wait for him to be the man?


B, Westmoreland


Love Doctor’s Answer:

The fear factor of rejection puts most people off trying to start a conversation. You obviously remain keen on this potential love interest. It is great that you are treading with some trepidation, rather than becoming overzealous, by contemplating whether to make the initial move.

As it was only a matter of days since you swapped cell phone numbers, then give it a week before you prompt him. You may be right about him already having a partner, and it was just a bar flirting exercise for him.

Alternatively, he is trying to play it cool or he is possibly not worth your time and efforts by lacking etiquette. Too many men in this day and age genuinely believe that they should be playing the waiting game to keep the lady guessing. This is a silly ploy that can backfire, and of course it can come across as controlling behaviour.

My suggestion is for you, after a week, to message him rather than make a call. Most men need a push when it comes to romance. So ideally shoot off a message with some humour, and suggest a cocktail rendezvous so that it jolts him and offers some value to a meet up. Do put your initial rather than your name, and ensure that you are showing interest by putting a kiss in lower case to him.

Here’s some examples that should generate a response:

– Do you find it sexy when a woman makes the first move or should I have waited for you? B x


– Remember me? Just wondering how you are getting on? Hopefully you are still enjoying those rum cocktails. B x

– Hi, let me know when you fancy more cocktails and conversation. B x

– Sorry to disturb you, I wondered if you fancied some company for another cocktail next weekend? B x

– I cannot figure out how I should begin this conversation. Maybe with a compliment about how handsome and charming you were? B x

– Hey, what sort of trouble are you getting into this weekend? B x

Most men enjoy a challenge, and your choice of message hopefully will flicker some interest. If he’s genuinely keen on you then he would be foolish to let this golden opportunity slip away, otherwise what was the point of exchanging numbers?

Then you have to play the waiting game, and if there’s no response then don’t waste your efforts on him as he would most probably be a lousy boyfriend who would not give you the attention you deserve. His loss rather than yours.

Although most people message rather than make a call, if you prise open the channels of communication then don’t limit the conversations to just texting after a while.

If you can land a date, are able to impress him and like each other, inject a phone conversation into the equation every now and again. This will be a terrific litmus test, because you will want to ensure that he can actually hold a decent conversation with you rather than his very short messages by text or WhatsApp.


With men and ladies having equality in the dating world, I urge you to go after what you want without coming over like an overeager puppy dog. Do give him a week to text you first before you make the first leap, so that can suffer a bit and he may realise what he’s missing.

If he still doesn’t respond after a week then by all means make a move, although if he fails to reply then rest assured that you can do better and he is a time-waster. However, he may be swamped with commitment, such as work or family. If he hasn’t got time for a part-time job then he certainly doesn’t have time for a relationship with you.

If it is all going pear-shaped then ask your friend who was at the bar with you. Her opinion will be unbiased, she will tell you whether it’s best to back off or chase him.

If he is going to be a gentleman who isn’t playing games then he will apologise for the delay in getting back to you, and suggest a rendezvous.

On the other hand, if he’s no good then you’ll never hear back from him. His steely silence is insulting, because he has played with your emotions. The sort of man that reverts to using silent treatment is not ever going to be happy with any lady, so you will have done well to have swerved him.

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