I Need More Than Flirty Fun But How Do I Land A Date? Help Me Love Doctor

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


How can I get a date with men I meet and like?

I’m baffled because they flirt like crazy, yet they never ask me out.

Shelley-Ann, Kingston



Love Doctor’s Answer:

Love Doctor MontiEmbarking on a potential new relationship is not as easy as it used to be. It sounds like hooking the first date is becoming a bit of project for you.

One of the things that may be putting off a new beau is that you are invariably coming across as emotionally needy. A tell-tale sign is when someone leans towards the other person when in conversation, so try to avoid that.

Ensure that you are not at all clingy when you meet a man that you like. If you believe that there is a connection then you need to play it cool but not aloof.

Men tend to lose interest when a woman on him like a rash. Sure, he is delighted that you are so attracted to him, but he wants to be the one to undertake the chase.

Another quick way to kill off the thrill of the chase is by initially revealing too much about yourself. If he learns plenty about you over a couple of drinks in a bar, then unless it is merely lust there’s not much chance of you going on a date. He knows all about you already, so there’s not going to be much mystery in a date.

However, there’s a tried and tested trick you could employ. This tends to work wonders for when a lady knows that she will constantly bump into a love interest at a certain venue around the same time each day or week. However, for this old trick you do require a male friend to act as a stooge.

By asking a man, who could never be more than friends, to join you in this deception is crucial. He can assist you in turning this potential beau’s head.


All you are doing is showing this love interest that you are attracting other men. This should make him partly jealous as well as let him realise that he’s not the only one romantically interested in you.

This simple trick of having a male colleague or friend intensely flirt with you near a potential beau works. It should prompt him to ask you out, as long as he’s interested in you romantically and obviously unattached.

After you have implemented this trick there is a follow-up plan. The next time you get a chance to speak to a man you have a genuine interest in, without your stooge nearby, then you can unapologetically flirty in a delicate manner.

Flirty fun includes the two must-do actions of locking his gaze with unnerving eye contact and subtly mirroring his actions.

He will feel flattered by your attention if you smile and nod at him when he offers an opinion. When a man says something humorous ensure that you flick or touch your hair as you chuckle. Show that you care by removing something, pretend if necessary, off his clothing such as a strand of your hair.

And when you are about to disappear from him, even if it is only briefly to powder you nose, try to leave a lasting physical impression. Give him a tingle by lightly brushing his hand or leg by accident as you get up. On your return, ensure that you touch him on the hand, knee or shoulder when you say something like “Sorry, I hope I didn’t keep you waiting too long”.

Every man knows that a woman will not physically touch a man unless she likes him, so this action will definitely boost his ego and have him eating out of the palm of your hand.

Should this man still not take these signals to ask you out then you need to seriously up the ante. A quick way to success is to start making an impression on his friends and/or colleagues, because if they like you he has the seal of approval to start chasing you.

To show his friends and/or colleagues that you are special then you simply need to ooze confidence. We are all generally attracted to those who act, look and speak with an air of confidence. Just make sure that you don’t come across as arrogant, as that would jeopardise your plans.


Men are naturally drawn to feminine energy, so dress to impress in what makes you feel good. Once your femininity draws the attention of his male friends and/or colleagues, this will not go unnoticed by him. Ultimately that should mean the has the desire to chase you for a date.

Once he has plucked up the courage to ask you out there is no need to snap his hand off, otherwise it undoes all of your endeavours. You need to stick to your plan to make him curious about you, as well as keep him dangling.

When he suggests going out for a dance, dinner, drink or perusing an activity then the best to do is to pretend that you are unavailable on the first night he suggests. Be a bit nonchalant by stating that you busy. This will leave his imagination running wild, and plants the seeds of doubt as to why his suggestion was refused.

You are now on his mind, which enhances your chances of a long-term healthy relationship. 

Don’t ever offer to change your plans for a first (or second) date to suit him. It’s good to show him that you are busy and not readily available when he wants to see you.

This will not only make you more memorable to him, but it also slightly dents his ego. Ultimately that means on your early dates he will be extremely determined to prove to you that he’s boyfriend material worthy of your attention.

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