Woman texting









Back in our twenties, the rules for dating were straightforward:

1. Look as ‘hot’ as humanly possible with the resources available.

2. Don’t allow looking ‘hot’ to prevent you from getting up off your chair due to tight and restrictive clothing, or from putting one foot in front of the other because your shoes are so painful.

3. Try not to drink so much that you end up wittering inanely or throwing up in a cab.


Dating in middle-age (i.e. over 40, not Tudor England) is a daunting prospect.

For anyone on the dating scene now, not only is life in general more complicated – considering whether to Tweet, message or Facebook him, for example, is far more tricky than simply having to wait for your entire family to go out so that you can make a private (and potentially humiliating) call on the communal phone strategically placed in a drafty hallway.

To make finding your life partner even more complex, over the years, all of us accumulate personal baggage and these days, you may feel a lot less inclined to put up with complications and being messed around.

I can’t profess to be able to help you figure out just what it is that middle-aged men want from a date, but, if you are totally flummoxed by what to wear for your first date in years, here I might be able to help!

Here are my rules for Hot Date Dressing:

The Don’ts

  • Wearing Red Lipstick.

You might feel very glam in your carefully painted red lip BUT it will stain your coffee cup or wine glass. This will remind ‘him’ that, if he kisses you, it will be all over him too. Red lipstick in particular seems to bleed more easily and make a mess, and, unlike your best friend, your date will not tell you when you’ve got lipstick on your teeth. Embarrassing.

  • Too Much On Show.

You want him to find you attractive so you might think you need to dress in an overtly flirtatious way. STOP!

Choosing one part of your body to reveal is more than enough. It could be your long legs, your arms, your cleavage or even just a subtle skin display, like your forearms or décolletage.

You are not sixteen anymore, you are a sophisticated woman, sexy in your own right, but not desperate.

  • Dressing in a way that isn’t authentic to you.

You all know how I feel about this: when you wear clothes that aren’t your usual style, there’s a danger that you won’t feel like you. If you don’t feel like you, you might not act like you. If he falls for you but it isn’t really you, you really will have a problem.

The Dos

  • Dress for you

If you feel comfortable and feminine, you will relax into the conversation and are more likely to have a good time.

This means:

  • Don’t wear towering heels unless that’s what you always do. Let your man feel like a man. The quickest way to put him off is to turn-up and be a foot taller than him.
  • Don’t trowel on the make-up. Research shows that men (believe they) prefer women make-up free. A gentle enhancement of your features and cover up of bags and blemishes is enough.
  • Select either your cleavage, your arms or your legs to show off. Leave him guessing about the other bits.
  • Don’t wear anything that requires careful arranging and constant re-arranging. The simpler, the better. Fussing over your clothes makes you look high maintenance or nervous.
  • Play up your strengths.

If you have a tiny waist, show it off. Great calves? Wear a pencil skirt. Lovely décolletage? Wear an open necked top.

Choose a colour that flatters your skin tone and makes you look healthy. Our primeval programming means that we are naturally attracted to people who appear to be bursting with life and not as though they are about to keel over, bringing no end of trauma to our calm and peaceful middle-aged set up.

  • Be you.

If he falls for the woman you are pretending to be the relationship is over before it has begun. Unlike back in your twenties, if you don’t like football, you don’t need to pretend to like football. (Seriously, don’t do this, or you could end up watching every Rumbelows cup quarter final for the rest of your natural life).

You will want to show this person the real you. So dress to express who you are. Feeling and showing confidence will give you amazing powers of attraction and you will feel far more self-assured, if you dress in something that makes you feel comfortable but sexy. If you need help working out what this could be, contact me, I’d love to help.

Most importantly: don’t forget, times have changed so much that your date may also be nervous about what to wear; a washed out ‘Jamaica, no problem’ t-shirt and dirty jeans are no longer considered acceptable date-wear for the 21st century man. Amen to that.


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