Dear Love Doctor

How Do I Retrieve The Art Of Flirting? – Help Me Love Doctor

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


With this social distancing dragging on, I find myself way out of practice with flirting.

Any tips for when we return to some semblance of normality?


Cassandra, St Andrew

Love Doctor’s Answer:

Love Doctor MontiFine-tuning flirting skills should automatically be updated throughout your life, similar to modernising your appearance and attire.

However, you are not alone in re-evaluating your amorous advances. So many singletons find themselves way out of practice because of the Covid-19 pandemic, with an incredibly high number having lost their romantic mojo.

Toying with making flirtatious conversations to virtual strangers has been extremely difficult an unnerving. The dating scene is becoming a quagmire as chance encounters appear to the thing of the past.

As sexual beings we all seek that magic spark with someone special to complete our own love jigsaw, but a certain amount of flirting is necessary to connect with someone.

Digital dating can be torturous with the numerous pitfalls, while organised events are fun but difficult to find because of the pandemic restrictions.

Therefore, many individuals will feel more confidence in simply sending something from afar. My advice is to avoid social media channels, as it takes the mystery out of you and opens up a can of worms if the potential relationship falters.

My recommendation, if you feel too shy to make contact with someone you like or previously dated, is to let them know you are attracted to them via text message. If you wish to kick-off a potential romance text messages can trigger things off.


However, you could be playing text tennis for months unless you go for the kill and send a message, when appropriate, that reads “Want to have this conversation in person?” The answer that he/she sends to that will determine whether it is just flirty fun that will never materialise into a potential date.

And if you land a date, then on the morning send something to maintain the mystery and interest such as “You will to love the outfit I wear tonight” but do not respond to any questions about this as you wish to remain enigmatic.

Text message suggestions:

Although I don’t have anything really interesting to tell you right now, I’ve messaged as I really wanted to communicate with you.

Even when I am with you, I cannot seem to get close enough to get to know you.

Just to let you know that I’m using my last 3% of battery to text you that I’m thinking about you.

Look at this ridiculous pic of Spot. He told me to tell you: “Woof.

Seeing your name pop up on my phone screen makes me smile.

What is your week looking like? Any room for me?

For those who don’t have their cellphone number or it is a total stranger, then the best bet is to simply walk straight up to them and utter the magic words of “Hello, my name is Cassandra, what’s your name?”


A tried and tested trick is to reply that “Oh that’s my father’s middle name/my grandfather’s name etc”, which you should admit on your date that that you were only kidding about.

Many find this scenario to walk up to an attractive individual awkward, yet it is often preferred to a cheesy chat-up line. I urge you to only make an approach if you have experienced eye contact with them and smiled, otherwise you will make them feel uncomfortable. 

If there is mutual attraction then the body language should indicate the genuine excitement that you initiated a conversation. Be bold and break the touch barrier early on to reiterate that you are interested, for example a gentle touch on the arm.

Next is to throw in some genuine compliments that should boost their confidence. Brighten their day by telling them how much that their jewellery/outfit/shoes suit them and match their eyes/hair/smile. Remember that all singletons have pretty much been starved of attention for so long, so this will be welcomed.

If you are simply seeking a bit of fun then opting to use chat-up lines are terrific for banter. But if you are after a potential relationship then get to know them better and ask questions. I suggest that you avoid the usual ones that cover age, car, children, emotional baggage, job and pets – save those for the dinner date.

You must maintain an air of mystery about yourself to keep your sexiness, otherwise there is little point on going on a date if everything about you is already known. Listening is a high-rated skill, and an especially attractive one for those who have been socially anxious after months of isolation.

My advice is to be honest and direct with someone that you are romantically interested in. Face-to-face you can state “I seem to have lost the art of flirting, do you think I can get it back?” The response will determine whether there are sparks flying or not. And if there appears to be a mutual connection then you can be frank and suggest exchanging cellphone numbers.

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