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How to Prepare Properly & Successfully For A First Date

Dan Western



How to Prepare Properly & Successfully For A First Date

Previously we’ve discussed motivating yourself to approach women and having the confidence to ask for a date. But what happens if she says yes?

You might spend so much time just getting to that point, that you are actually unprepared for the date itself. But fear not, as organizing yourself before a first date is easy and simple when you know how. Let’s go through it all.


How to Prepare For A First Date

Here’s the basic guide to preparing properly for any first date:


1. Confidence Starts with Your Appearance

If she said yes to a date, then she obviously likes your look, so you don’t need to change it dramatically. She might like men with a slight beard, and could be disappointed if you’ve shaved it off to appear tidier!

If you feel more self-assured with a beard and longer hair, then don’t change a single thing.

Self-assurance goes out the window when you start to change yourself based on what you think others will like.

Similarly, what you wear will make a big impact on how you carry yourself through the date. If you’re the kind of person who feels more comfortable in black jeans, sneakers, and a plaid shirt, then that’s the best version of you. Many girls like that type of look on a man, so simply wear what makes you feel good.

Dressing up does have its place, of course.

A fine sports jacket like these examples is totally appropriate if you believe that’s the type of man she likes and you love wearing one. If you put on something that isn’t normally you, then it will come across on the date – she’ll be able to tell that you’re uncomfortable.

If there’s anyone who can confirm that confidence in what you’re wearing is crucial, then it’s women themselves! Stacey Smith (menswear buyer from, Naomie Harris (actress) and many more women discussed what they believed made men eye-catching.

“It’s about wearing what feels comfortable, and having confidence in how you dress – some of the best-dressed men ignore ‘the rules'” – Stacey Smith

“It’s all about confidence. Being comfortable in your own skin, there is something so attractive about that” – Naomie Harris

If women are happy with you wearing what makes you confident, then you should be too.

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2. Suggest Options for the First Date

So, she wants to meet you soon – that’s the hard part done!

Once you’ve worked out a time that suits both of your schedules, now you’ve got to pick a place to meet. What you end up doing can depend a lot on the time of day, for example, if you can only meet on Saturday afternoon, then suggesting a good coffee shop or park to meet up at are good ideas.

Conversely, if Wednesday night is the only time she is free, then meeting at a bar or concert can be great first dates. Having a first date at the cinema is perhaps a bit old hat nowadays, but if you want to do something a bit more action-packed, then something like bowling or a casino can be a lot of fun.

Not everyone likes the idea of eating in front of someone on the first date, so perhaps save the restaurant for a later date. Check for special events like art gallery openings or markets, as these can be great conversation starters.

The main thing to remember with a first date is to suggest a few different options (but not too many!) and see what she prefers. Be open to her ideas as well, as she might know of a bar that she feels more comfortable in. Simply chat back and forth and come to an agreement on where to meet for the date.


3. Think of Topics to Discuss

While we’re not suggesting you need to bring a script of what to say, it is a good idea to have some topics in mind before the date. If you know she loves movies, then ask her what she’s seen lately and her thoughts on the films. Likewise, if you’re aware that she travels a lot, ask about her experiences and where she’s going next.

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If you’ve been texting before the date, then you’ll probably have a rough idea of what she’s into and her personality, so have some topics in mind before the date, but also be spontaneous. No one wants to answer boring job interview questions like “Where do you see yourself in five years?” Try to have fun and ask interesting questions.

Oh, and don’t even think about pretending to like something just because she does, as you’re bound to get caught out eventually.

If you said you love The Beatles but can’t think of a single song when she asks your favorite… don’t expect the date to last long, let alone earn a second one. Either find common ground or perhaps discuss why you don’t like something she does, but never lie.


4. Be Cool, Calm, and Collected

First date butterflies is totally understandable, especially if it’s been a while since your last date. But what’s vital to keep in mind is that she’s likely going through the same feelings as you. First dates can be a little awkward in the beginning; after all, you’re basically strangers meeting up and don’t know much about each other!

Even if you’re squirming on the inside, do your best to remain relaxed on the outside.

People usually loosen up after chatting for about an hour, so just keep reminding yourself the three C’s: Cool, Calm, and Collected, and you’re bound to ditch those nerves before long.



It’s almost impossible to know how the actual date will end up, as you might click or you might not. However, if you know deep down that you did everything you could to plan well, then that’s all you need to know.

If you dressed and styled your hair in a way that makes you feel cool and confident, chose a place that suited both of you, and were relaxed, charming and funny throughout the date, then there’s more chance of getting a second date.

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How do you prepare for a first date? Leave a comment below.

Dan Western is the founder of Wealthy Gorilla. Dan has been running Wealthy Gorilla and studying self-development, personal finance and investment for the last 7 years, whilst traveling the world and being able to call Bali, Indonesia, his HQ. To this day, Wealthy Gorilla has become one of the fastest growing self-development sites in the world; with over 160 million views worldwide, and more than 200,000 followers on social media. Dan's mission is simply, to inspire others to live their dreams and be the person to whom they say; "Because of you, I never gave up."