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Everything You Need to Know for a Great First and Second Date with a Woman

Pretty woman on a first date

So you’ve bagged yourself a date and now you’re in need of tips for the first date AND the second date so you don't screw things up. You don't want to have such an incredible first date that you can't follow yourself!

Many men aren't great at first or second dates and feel nervous ahead of the big day, but try not to worry. There is a proven formula that you can follow to ensure that the first couple of dates go exactly as planned.

But it can really help to find out more about what women are looking for and how to talk to them before going on that first date.

Our Top Tips for a First Date for Guys

In this article, we’re going to cover our top tips for what to say and do on that all-important first date with an older woman.

These tips will be useful in any situation regardless of if you initially met in person or through one of the websites from our annual review of the best websites for dating older women.

While many of these apply to being on a first date with a girl of any age, some of these tips are specific to dating attractive women.

Let’s get started with some of our favorite do and don'ts on a first date:

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1. Take her somewhere different is a first date tip that is overlooked

Man and woman looking at a sunset on a dateYou need to make yourself stand out from all the other guys this woman could date. So, how do you do this?

You get creative of course!

This begins before you even get to the date.

An older woman has probably been on more first dates than you could imagine. So taking her out for coffee or a standard meal isn’t going to impress her.

Use what you already know about her to plan a fun and unique first date. Maybe you take her to play crazy golf or to a cocktail making class. You can pack a gourmet picnic and head to the beach.

If you’re stuck and need a little help, here are some ideas for your first date with an older woman.

2. Be yourself

Woman encouraging you to be confidentYou might have convinced yourself that because she’s older than you, you need to pretend to be someone you’re not to impress her. If this is true, then she’s not the kind of woman you want to date anyway. But most women won’t want you to wear a mask. They will enjoy your company even more if you’re authentic. Plus, it’s easy for us to tell if you’re not being genuine.

First dates are all about getting to know each other and see if you click. What's the point of making it to the next date if she hasn't even seen the real you yet?

So always be yourself. This is the only way to tell if the two of you have a genuine connection.

3. Our best tip for a first date with an older woman: be playful

Guy being playful on a first dateDesireable women enjoy how most younger men are more fun, playful and relaxed. This is where your age gives you points because men her own age tend to be fairly serious or even cynical. First dates are supposed to be a good time while both of you are getting to know each other!

So don’t be afraid to tease her a little. Make some jokes and don’t take yourself too seriously. Just in case you need reminding, it’s best not to make jokes about ethnicity, religious beliefs, personal ethics, or her age. You still don’t know what kind of humor she likes, so it’s best to play it safe and not cause any unintended offense on the first date.

4. Don’t mention or discuss the topic of her being older than you

Woman staring at a younger boyIt’s probably obvious that you shouldn’t joke about her age. But it’s also important that you avoid mentioning or discussing her age in any way.

While it’s okay if she raises the subject during your first date, you must avoid raising it yourself.

That’s because you can’t be sure that she won’t be offended in some way.

Quite simply, you should act as if an age difference was never the case. You’re just out on a date with a woman who interests you. Age is irrelevant.

But if she mentions how young you are, gently remind her that age doesn’t matter to you and you date people based on how strong of a connection you have.

5. Compliment her ONCE on her appearance

Couple staring on a first dateAll women like to be told they’re beautiful. Attractive women tend to hear comments like this from men less and less as they get older. So if you do find her attractive, don’t be afraid to tell her.

But as soon as you have, try and keep the rest of your compliments to things that are non-physical. You don’t want her to think you’re only interested in a hookup, especially before you know what it is she’s looking for. Guys who can't stop complimenting women are putting up a big red flag that they're either insecure or don't understand women.

So take the time and effort to actually pay attention to what she tells you on the date. Then do your best to find something non-physical to compliment her on. This might be an achievement in her career, a hobby she’s involved in or even something crazy she did. This is a useful first date tip.

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6. What should you expect on a first date?

You should expect to have fun! Way too many guys are super serious about how they approach dating and turn the first date into an interview instead of a fun way to feel out other out and get to know each other. If you're not laughing and having fun you're doing it wrong!

You want to arrange things so that both of you will be comfortable and able to relax a bit and enjoy your time together. If you get dressed up and spend all that money on a date you want to get the most out of it. You will both be nervous so try to keep things simple at first. Going all out on the first date puts a lot of pressure on both of you for things to go well.

7. Is it ok to kiss on a first date?

Absolutely (we wrote an entire article about if you should kiss on a first date and that's the gist of it)! In fact, it's usually a very good idea to go in for the kiss before you get to the end of the date if you're feeling a good connection. For many women, especially hot women, a kiss is not really a big deal at all. It's definitely a step forward in the relationship but not a huge one!

When you go to kiss a woman confidently but respectfully it sends all the right signals. Be respectful if she stops you but don't be afraid to go for it. There is little downside and if it doesn't go well just go on with the date like nothing happened.

8. First dates are tough but don’t put her on a pedestal

Complimenting an older woman does not mean you’re putting her on a pedestal. That’s because it’s ultimately your mindset towards her that determines if you’re overvaluing her in any way.

While she may be special in her own way, you have to avoid thoughts of seeing her as an extraordinary woman who has taken interest in you by chance. Otherwise, you will exhibit varying degrees of desperate behavior, which will harm your chances with her.

You can see her as an attractive woman. She might be fun to hang out with. So there’s no problem in seeing her for the cool woman that she is.

But don’t view her as some kind of rare, elusive woman who wouldn’t usually give men like you the time of day. They might have different standards and expectations, but they don’t want to be put on a pedestal.

9. Tell her why you like mature women

This is without a doubt one of the best tips for the first date with an older woman. Tell her the reasons why you like mature women. You can choose to be as direct as you’d like to be here.

Make it clear that you’re attracted to the things that only someone with her experience could offer. Tell her you’re over playing games and messing around--you know what you want now. You can also mention that you love that she seems to know exactly what she wants.

The truth is, older women do have a lot to offer that younger women often don’t. Looks are great but they always fade. Intelligence, kindness and wisdom don’t.

10. Be confident on your first date

All women, regardless of their age, are attracted to a man’s confidence. You don’t need to look like Bradley Cooper, drive a Ferrari, or make a million dollars every year to be confident. Confidence comes from within.

It all starts with focusing on all the amazing qualities that you have to offer a woman and remembering this when you’re chatting to her.

Stand up tall and keep your head high. Maintain strong eye contact when you’re talking to each other. Smile often. Speak clearly and avoid talking too fast.

Make sure you look the part too. Take the time to get a haircut and wear some stylish clothes. This will help you to feel more confident even when you’re struggling to. This is one of the best tips for any date.

11. Ask her what she values most in life

Even though you’re on a first date and want to keep things light and casual, there’s no harm in asking some more personal questions. This helps show her your maturity, and also helps both of you see if you’re compatible with each other.

Ask her what she values most in life.

Does she value her family and friends the most?

Are her health and freedom her top priorities?

Does she ultimately want peace and enlightenment?

Don’t be afraid to be open and honest with her and also share your own thoughts. Women love to see a man being vulnerable with them.

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12. Our top tip for a first date with her: remember that age is ultimately irrelevant

Lastly, we must conclude by reminding you that age is irrelevant. She might question you about it or you might have doubts in your mind. She will definitely have doubts of her own. But you must not see the age difference as an issue.

If you act as if her being older than you is trivial, then that’s exactly what it will be. What’s most important is the vibe between you--the chemistry that you have together. So focus on building a connection because there are no rules to dating but the ones that you establish.

You’re Ready to Impress with These Tips for Your First Date

You’ve now got the basics covered when it comes to dating an older woman. The rest can only be learned from real-life experience. So, all that’s left for you to do is get on out there and take an older woman on an incredible first date.

Always remember to be yourself, ignore the age gap, and focus on enjoying each other’s company.


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