How should I prepare for my first date?

So you’ve clinched it! You’ve got beyond the endless messaging to actually arranging a date! What should you do next? Here are some tips from someone who had 22 first dates in 2016, plus some stories from my clients ….

  1. Where are you going to have your date? Many seasoned daters say meet for a coffee for the first date. Then it isn’t too expensive and you don’t waste a whole evening if things are going badly. This means it will be less romantic, but that’s no bad thing the first time. Creating an artificially romantic frame for a first date can encourage false and premature intimacy, emotional and even physical. If you don’t like them in the cold light of day at the beginning, then there’s not much point – assuming you’re looking for a relationship rather than a one nighter.
  2. How long should the date be? Keep it short – if you both go away wanting more, that’s a really good thing. I’ve had very long first dates that have been amazing, but you need time alone to reflect, to go over what was discussed, what was left out that you need to find out about next time, were there any warning signs, how you feel now you’re away from them. You simply can’t do this when you’re together. If things are going really well your judgment will be flawed because your emotions will be getting in the way. How you feel the next day is a much better measure than how you feel when you’re with your date. I would suggest one to three hours maximum. 
  1. What should I wear? Really I’d need to see you in a few outfits before I can decide. (When I did my Seven Dates in Seven Days Challenge, I wore the same outfit every time to eliminate extraneous variables … And yes I did wash it in between ….) It depends on your age and where you’re going, but in general I would advise: 

For women: Smart but not too smart. For example, I often wear a short skirt with black tights or leggings and ankle boots, with a more interesting top. Personally I would say don’t wear heels AND a short skirt … Fashion gurus say this is too much, that you need to balance glamorous with casual to get the right effect. You don’t want to appear to be trying too hard but you want to be stylish. Tom suggests: “Don’t dress as if you’re going to the allotment. Smart work clothes are fine for after-work drinks. Dress as if you’re going out for dinner but not to a wedding. Show that you’ve made an effort – that shows you value your date.”

On the other hand, many of my older clients complain that women they date are dressed too sloppily in jeans and an old T shirt, or even sportswear– a definite no-no.

Make sure there isn’t a big discrepancy between what you’re wearing in your photos and what you wear on the date. Women often post pictures of themselves dressed up to the nines and then it can be a disappointment when they turn up in a sweatshirt.

David’s advice is: “Study the way your date dresses in his/her photos to get an idea of what dress style they value.” John says: “I like women to wear some but not too much make-up. Many go to one extreme or another.” Stephen advises: “Wear a little make-up to show you respect the occasion. Don’t wear jeans or trainers. Men have often gone through a lot of rejections when dating and it helps them feel good about themselves if they feel the woman is dressing in a way that means she’s taking the date seriously.”

For men: Men are often TOO casually dressed for a date. Personally I like my dates to wear shoes rather than trainers, and something with a collar. But others may be happy with more casual. Make sure everything is very clean, polished and ironed and fits properly. Don’t just wear black, grey or navy blue – try to be a little more interesting! Get advice from female friends, especially about your jacket – you can ruin a good outfit with an unflattering jacket. Don’t wear shoes that are too casual for the rest of the outfit. Amanda says: “Any kind of sportswear, including caps, is out.” Rebecca thinks a suit is too formal. Jo says deck shoes are a no-no. But I don’t mind them!

I suggest you read my blog post on Aromatic Dates to make sure you’re smelling your best. It might seem obvious, but about 50% of my dates last year didn’t smell good.

And don’t forget to wear a smile! Very important.

  1. How much homework should I do about my date? If you’ve met them online, you need to memorize their profile. It shows that you’re really interested in them as an individual, and that they’re not just another date in a big long line of (mostly failed) dates. Personally, I don’t read through their answers to all the questions (e.g. on OKCupid) because then you’d have nothing to talk about. If you’ve met through a Meetup event, you can check out which other Meetup groups they’re in. If you’ve met through a friend, you could ask the friend for more information – but then they’re bound to go and tell them! Many people google their date too. But don’t tell them if you do. It makes you sound like a stalker. However, if you decide to go somewhere to eat on your first date, do ask them what kind of food they like before suggesting somewhere. And if you want to go to a bar, make sure they do actually drink. 

makingnotes

  1. What are some good questions to ask on a first date? “Prepare what to say on the date? I’ve never done that before!” I hear you say. But I think a date can be a work of art and that doesn’t just happen, however amazing your social skills. Think of it in the same way you would going for a job:
  • What do you actually want to find out about them?
  • What can you follow up on from their profile and find out more about?
  • What is missing from their profile that you want to know?

To do this effectively, you’re going to need my 100 dating questions – purchase them here. Obviously don’t bombard them with too many – they don’t want to feel like they’re being interrogated. And not everyone likes it when you get out your list …. Although some guys I’ve dated loved it, which in itself was a Very Good Sign. (Some of my clients have notebooks, especially when they’ve got several first dates lined up in a week – which is a Good Thing, by the way. More on that another time.)

You need to plan the questions to start at a more superficial level, and gradually move deeper if you feel it’s appropriate. My questions are graded on three levels of depth. Don’t forget to ask your date back the same question they ask you – it’s clearly something that’s important to them.

  1. What are the common no-nos on first dates?

This list could be very long ….

  • Having your phone on and out on the table
  • Not making eye contact
  • Making eye contact with other women
  • Watching the football on the TV screen in the pub
  • Not responding verbally to what your date says
  • Telling your date why peanuts are not actually nuts or other boring facts
  • Talking about sex (at all, probably, but especially within the first hour)
  • Arguing
  • Talking about your children for more than about two minutes
  • Talking about your ex
  • Talking for more than two minutes at a time generally
  • Telling lots of bad date stories
  • Being negative about yourself, others, relationships, life generally
  • Talking about really personal stuff like medical conditions or your shaving habits
  • Saying “Oh, you look shorter/older than in your pictures!” even if it’s true

Do send me your own examples!

  1. Who should pay? As a woman, I would always offer to go halves, or pay if it’s just coffees. Men have a lot of dates and often have to pay, and that’s not fair. Men, you should feel no qualms about asking to go halves, especially if you’re not getting good vibes about it leading to another date. Just say confidently “Is it OK if we split the bill?” However, if you REALLY want to pay, and the woman doesn’t object too strongly, that’s OK too! Don’t let the woman order an expensive bottle of wine without discussing payment first. The woman should make it clear early on that she’s willing to go halves if there is going to be a big bill. But if you don’t want to end up forking out for a big bill, go to a coffee shop! 
  1. How should I end the date? It’s always good to be the one who ends the date. Then you are in control, appearing to be confident and having other things to do, and the other person is left wanting more (hopefully). Don’t talk about whether you want to meet again at this point. You should both go and away and think about it for a few hours. If you’re pretty sure you don’t want to meet again, just say “It was good to meet you”. If you think you might be interested, say “I’ve enjoyed getting to know you and I’ll be in touch”. If there has been no physical contact, you could kiss on the cheek. It’ll be clear if the other person is receptive to a kiss on the lips. If I wanted to kiss on the lips and wasn’t sure what signals I was receiving, I might make a joke out of it and explicitly ask “Do you think we’re at the kissing stage?!” But usually it’s pretty obvious. 

Don’t prolong the goodbye or waffle on embarrassingly. Be decisive and don’t look back. Continental men see their women all the way home, apparently, whereas British men will walk a woman to the tube or bus stop if they’re lucky. There is nothing to stop the woman walking the man to his bus stop or tube if that is equally safe, however.

9. How soon do I communicate after the date? Then I wouldn’t text for a couple of hours at the absolute minimum, even if you’re really keen. There is a very delicate balancing act here between showing you’re still interested and coming on too strong. This is a point at which a lot of people need coaching, because you can easily say the wrong thing.

10. What do I say after the date? If you’re interested in a second date, just say so in a text: “I really enjoyed our date and I’d love to see you again. Perhaps a walk or dinner next time?” Sound confident but not needy.

If you’re NOT interested, say something like: “I enjoyed meeting you but I’m afraid I don’t think you’re right for me. All the best for dating!” or “That was fun but there wasn’t any chemistry for me, I’m afraid”. Don’t be patronising or overly apologetic. Don’t just not text them – that’s cowardly. Treat them as a fellow human being.

If you get the thumbs down from your date, you may want to ask them for more feedback. It can be very useful if you are having trouble getting past the first date. Just ask: “I’d love to know if there was anything you think I should have done differently, or a bit more detail about exactly why you didn’t think I was right for you.” It’s risky for your self-esteem but in the long run it will be useful to know whether there are things you can change, or whether they are always things out of your control.

Dates should be FUN!

Remember, dates should be enjoyed not endured, but many don’t lead to a second date, so if you expect that, rather than getting your hopes up, you can treat them as good dating practice and an enjoyable way to broaden your horizons by meeting new and different kinds of people. Try to learn something new on every date, whether it’s factual or personal.

laughing on date

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