How to Win on a First Date

If you have ever heard the expression ‘Clothes maketh the man’ – this is true, well, partly true. Bear in mind that your date will be scoring you from the very first second – even before you have opened your mouth, so no pressure then!

You want to create the ‘wow’ factor – and that doesn’t necessarily mean wearing the most expensive clothes, the fanciest watch or the most over-powering aftershave. In fact, quite the opposite, these things can turn a date off, again, even before you have opened your mouth. So what should you do? Well, thankfully I have prepared a quick cheat-sheet for you:

  1. Make an effort. This sounds obvious but you should look and smell clean, with neat hair, clean and cut fingernails, nose/ear hair taken care of, eyebrows neat and facial hair, if you have it, well presented – like you have made an effort. If your date feels you have made an effort they feel valued and respected and this instantly makes you more attractive.
  2. Dress for the occasion. Know what you are going to be doing throughout the date and make sure that what you are wearing suits all activities – so don’t wear jeans to the opera or a dinner suit to the cinema – just something that is smart and appropriate to the event. If you go overboard, you and your date will look odd together. You want to compliment one another’s looks.
  3. Be yourself. This is always good advice, whether you are on a date on in a job interview – you will feel most comfortable if you are being your authentic self. Pretending to be wealthier, more successful or smarter than you are will ALWAYS come back to bite you. Trying too hard to be funny will often backfire – always looking for the joke in any sentence becomes tiresome. Bide your time, let the conversation flow and when something funny naturally pops into your head it will come across more spontaneous and funnier as a result.
  4. Be interested and interesting. Ask your date about their family, their job and their hobbies. Look for common ground and share your areas of commonality. Don’t interrupt like an excited puppy every time they say something that strikes a chord – listen to what they are saying then add your bit. If there is no obvious common ground, probe into their job and free time more – if there is anything unusual, questions like ‘Oh, that’s an unusual hobby. How did you get into that?’ will allow them to relax and open up. If you find yourself doing the majority of the talking, it’s time to take a breather. We know that you are hilarious and interesting but the goal of the date is to find a mutual attraction. If your date doesn’t feel listened to or that you are interested in them, that mutual attraction is unlikely to happen. Even a conversational segue like ‘Anyway, that’s enough of me, tell me more about [insert their interesting job/hobby/skill etc]’
  5. Recognise their effort. The chances are your date is just as nervous as you and went to a whole lot of trouble preparing for the event. You will be able to spot the areas where most attention has been lavished – hair, makeup, outfit, accessories. Pick one and pay a nice compliment – but be careful, this is easy to get wrong. Stick to something that’s not going to trip you up like ‘I love your hair’ or ‘that suit looks great on you.’ Then stop. If you start to list their hair, their makeup, their shoes and compliment them all it immediately sounds insincere and trying too hard. ‘That makeup must have taken ages’ sounds like a compliment. Your date will hear ‘You are wearing too much makeup’. ‘Ooh, is that a Rolex?’ will sound like ‘I am shallow and am only interested in brands and labels’. If you do want to compliment your date on their watch, just say, ‘I like your watch’ and see what their reaction is. More often than not it will have been a present or an heirloom, in which case they can elaborate, which again gives you an opportunity to show interest.
  6. Be modest. In the same way as being brash and showy is unattractive, being modest is a very attractive quality. When asked ‘what do you do?’, you can answer in a number of ways, each of which is the truth but equally, each comes across very differently. Any answer that starts ‘I’m the CEO…’, ‘I own…’, ‘I run…’ basically is designed to let your date know that you are a big deal. A better way is to describe what the company does. This is inherently more interesting as it invites questions about that sector, and as it is your company you should find it easy to talk about. You can then go on to talk about your team and your role if they are sufficiently interested.
  7. Give the right signs. Give the date every chance to succeed. If you show interest, listen, ask appropriate questions and laugh in the right places your effort will be reciprocated. If you decide after five minutes that there is no spark and spend the rest of the date checking your phone then there really is no point in being there. Phones should be out of sight for the duration of the date and even if the server or the person on the table next to you looks more fun, never flirt with them. This is highly disrespectful to the person you are with. I would suggest that even if a date is going badly and there is no spark, at least make it to the end of the date out of politeness. You have both made an effort to be there and would both like to get something out of the date, so just try to make the best of it. You never know – you may be able to turn it around and find some hidden gem of compatibility.

I am by no means guaranteeing that these tips will make you irresistible, or that you will have success on every date, but if you follow this advice you will definitely give yourself the best chance of success.

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