Dear Love Doctor

How Do I Actually Secure A Second Date? Please Help Me Love Doctor

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


My dates seem to go badly, as they end up as just one date. I always go out dressed smart,  casual and sport a dress watch and a bit of bling. What sort of watch should I wear to impress on a first date? Should I tone down the bling?

Leroy, Kingston 5

Love Doctor’s Answer:

Sorry to learn that your dates are not ending up as you want with these various ladies.


Love Doctor MontiThe very first date is all about the expectation followed by sheer excitement. If there is a connection, a common interest and a physical spark then you are likely to be soon arranging a second date.

There are loads of tell-tale signs on the first date that you need to pay attention to, such as body language and whether you are asked “How long have you been single?”, so that you can determine whether she is interested in you.

You need to be prepared for a date, not just treat it like a set of questions as though it is a job interview for her or simply talk about yourself too much.

My main tips if you want to obtain a second date is to remain mysterious, be a great listener, throw in quips about doing things together and show utter respect.

Being mysterious means that you do not reveal so much about yourself on your first date that she knows absolutely everything she can about you. Otherwise there is little point of her going on a second date, because she will hear the same things about you.

So hold back your funny stories and impressive details, instead offer her a drip-drip feed of information to maintain her genuine interest in you.

Being a good listener involves you not only contributing around 20 per cent of the conversation on a first date, but also laughing, nodding and smiling at what nuggets of information she is revealing about herself. You need to be genuine, glean these details and be able to refer to them during the conversation so that she knows you are being attentive.


It is a great sign that there is a future relationship when one person begins talking about doing things together in the future. For example, if you start talking about how good you are at dancing and she says: “I am pretty good too. We should go sometime and see who really is the best dancer” then that is the signal to sort out a second date.

You should seize any more opportunities like this, to build on that excitement of getting to know each other.

I strongly recommend that you should close your date with the view to setting up a second date. You can either ask them while you are still out together, or the more modern yet vague approach is to let them know that you would like to go out again but not actually arrange anything.

Regardless, at the end of your first date I urge you to let the lady know that you had a great time – if you really did – and beam her a beautiful smile.

If you want to ask her out for a second date then and there you should offer her two options, here are some examples for you:

“I had loads of fun with you tonight and would love to take you out again. Do you fancy Sunday Dinner at xyz or to catch a movie during the week?”, and;

“Those cocktails were so delicious and I had a really nice time with you. Let’s get together sometime soon again to try others on the menu, let me know if Friday night or Saturday evening suits you best?”

If you prefer to walk away then message or call them, then do so within an hour of going your separate ways with a caring message along the lines of:

“I had a terrific time tonight with you. We should definitely do this again sometime. I will text you, and;


“Tonight was a lot of fun with you, maybe we can do it again sometime. I will call you.” 

Then if you text make it more personal and casual:

“Hey beautiful, I had so much fun the other night because of you. I would love to see you again. Do you fancy Sunday Dinner at xyz or to catch a movie during the week?, and;

The other night was a real blast with you. Those cocktails were so delicious. Let’s get together to try some others on the menu, let me know if Friday night or Saturday evening suits you best?”

As dating is all about momentum, then the key to securing a second date is about not waiting too long to see each other.

It is no use playing games and being coy by waiting days before you message her. Be direct and tell her that you had fun and would like to see her again, but you must offer her something to get her to say yes. Give her an incentive to see you, such as going for a cocktail, dancing, Sunday Dinner etc.

Do not wait too long between the first and second date. As time passes without seeing each other, then there is the real risk that any chemistry that you built will begin to fade.

Your other questions about your appearance are interesting. Smart casual is always a good option, but it depends on the venue and you really do not want to turn up in white sneakers or sportswear.

A light-coloured crisp shirt, cotton or linen, coupled with a smart pair of chinos is always going to work. Especially if you wear a jacket and a pair of sunglasses too. A modern suit jacket is something that ladies like to see on a man, it is a man’s armour and certainly gets looks off the ladies.

As for the bling. You can overdo bling if you are rattling too much when you are on a dinner date with the lady. It is always going to be off-putting for any lady to have a man more blinged out than her, so my advice is simply wear slightly less bling than your date.


With respect to your watch, then I would suggest on your first date (and second dates in the future) to opt for an oversized watch that shows the lady you are a real man. Yes you may have the diamond encrusted watch or a designer watch, but leave those at home because you are trying to impress your date about you and not your attire. The same goes for a classic dress watch, these tend to be high-end watches so save those for a dinner date or meeting her friends/family.

Armoured with this information, toning down your bling and sporting an oversized macho watch should have you securing second dates with aplomb.

However, do not forget to ask her “What made you go on a second date with me?” during your rendezvous. This will allow you to gauge whether a third date is on the cards.

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