Which is better, spontaneous or planned dates?

I’m going to be answering the question “should I ask for dates spontaneously or plan the dates out ahead of time?” You wonder which is better especially if you’re a little inexperienced with dating. Answering this question really aligns with timing because recently, I was on a Lyft ride with a woman and when she found out I’m dating coach, she expressed how she sees more men nowadays spontaneously ask for a date and not plan things out anymore. She wanted my insight on if that’s a common behavior all guys do and asked “where did chivalry go? Is it dead?” and it got me really inspired to talk about this today!

It just so happened that I saw this question in the ask Ruby form and then that happened. The question is, are her thoughts common with all women? Don’t women appreciate spontaneity?  Let’s make this clear for you!

Which kind of date is better?

Let’s answer the question, which one: Spontaneous or planned dates? Yes, spontaneous dates can be great, it’s adventurous and fun, right? However, it is actually better to plan the dates out. Why is that?

Just to clarify,  this is for when you’re asking for the date. This isn’t when you’re already in the date and you’re trying to figure out what to do in the moment (spontaneity is really great for on the date). This is if you texted a girl saying “hey, what are you doing right now?” and then a “7:00, my place?” Similar to this text below:

A spontaneous ask for a date is any form of asking her out out of the blue for a last-minute date. It’s normally the day of or even in the right now.  This form of spontaneity is NOT suggested to do for dates, especially if it’s a first date.

It actually does not work as as often as you may think. It only works if you’ve already been dating and there’s been a strong connection built there. When you already know you two like each other, being  spontaneous is great because it keeps both of you on your toes, on new adventures, and builds momentum. But if you’re newly dating a woman, it’s only been the first 3-4 dates or so, and especially if you haven’t met yet, spontaneity isn’t great.

Why wouldn’t women want spontaneity?

When you ask a woman if she prefers spontaneous or planned dates, they’ll pick planned. Here are some reasons why women actually don’t like spontaneity at the start:

• She doesn’t have enough rapport and trust built yet to rearrange her time for you
• She doesn’t feel like she knows you yet to be excited to do anything with you
• It could feel you’re pushing her to bend to you
• It shows you’re not as much of a gentleman, you do things only on your terms
• Most importantly….women have lives. 

You can see this chat below where she made it clear she has a life so he can’t just be springing up plans out of nowhere! Note: These screenshots are sent in by the woman so the texting bubble is from her perspective/screen

People, not only women, have a life! People have plans. Unless…of course, you know you both are super introverts and don’t like to make plans. Maybe you know they don’t have friends or family around them.You could think it’s okay when in your conversation, they say they’ve been chilling all day at home and love it. Sure, it maybe okay to ask because you share the same kind of lifestyle and you’d figure she’d be free. But, even so, they could have plans to stay in and have time to themselves. Most people will say this about introverted, shy, or reserved ladies….but they need to plan the most!

Introverted ladies need to know where there energy goes every day and plan to use it ahead of time. And they only have an allotted amount of energy to expend so that they’re not drained. Introverts are don’t feel drained only if they’re spending it with people they’re already close to. And, quite honestly in this case, you’re not close to her yet. So once again, I don’t suggest to do this if you’ve not seen each other or even if it’s only been the second or third date.

Planning a date

I do suggest to plan a date ahead of time, but don’t wait too long. The other side of planning a date that isn’t good is planning a date two weeks out. That’s too far off. And when you have something that’s far away, you have to hope that the texting momentum is on fire.

Of course, there are exceptions. If you need to plan 2-3 weeks ahead because you travel plans, that’s okay! Just make sure that’s known to her and she’ll appreciate you making time for her even with your busy schedule. And as you wait for the date, make sure you’re on your texting game. Because waiting for the date with all that time can make it very easy to forget. It’s easy to lose momentum, and then you lose the date.

How long ahead of time is the best time to plan a date

So, what is the perfect window to plan a date? It’s best within the week or 3-4 days prior to the date. If you text on a Wednesday asking what she’s doing on the weekend, she then says she’s free Saturday, that’s perfect! You only have two more days to plan things out, keep texting, and then it’ll already be time to see each other.

It’s best when planning out the date, you include her in on it as well. You can throw up (great and amazing) date ideas and options to show you’re taking the lead, but having her participate adds to the excitement. She’ll look forward to it more because it’s something she really wants to do.

You don’t want to make it all about you

When you ask her out spontaneously out of the blue, you’re not having her be a part of the process. You’re just saying “Hey, we’re doing this. Want to show up? Here’s where I’m going, come join me”

You’re not giving her a voice or decision on what to do. Has that forwardness worked? Yes. BUT, only if she’s extremely already highly interested in you — like how any woman would do anything if Ryan Gosling was in front of them. If you have a Ryan Gosling vibe, everyone already loves you and women are always throwing themselves at you. But, I’d assume if you’re reading this…you are not in the same boat as him and this isn’t the case.

Include her in the planning

Asking a woman out beforehand shows you’re not afraid to take the lead. Then, it’s best to include her in on it by first giving ideas and asking for her thoughts. You can ask something as simple as “Any sort of Cuisine you do or don’t like?” or “Have you heard of this area? Would you be open to exploring it?”

You’re still taking initiative to plan but allowing her to share what she likes and she enjoys so becomes more of a collaborative process. It gets her excited for it! Planning the date allows her to make time for you.

My own personal story as an example

I do want to share with you a personal fact/story! When I started out with my boyfriend, there’s actually a mix of both dates.  He definitely took the lead and planned out the options for what we could do, he asked me to choose what I’d prefer,  and after our date, it was very clear we had a deep connection. That’s when he would spontaneously call me and say “hey, what are you doing?” And in that moment, I would hesitate because I’d be working late or working on a project. I’d, then, think for a bit “I don’t know…” I had to decide if I wanted to  interrupt what I’m already doing for time with him. However, in my case, I had high very high chemistry with him, I really enjoyed his company. and there was already so much Rapport built. I trusted him.

Spontaneity is good, just not at first

So, it worked for us! I, also, love spontaneity as well 🙂 And I think a lot of women do too. Remember when you’re thinking of spontaneous or planned dates, know it’s okay to be spontaneous on the date! During the date, maybe you’re exploring an area, and you spontaneously hop to one bar to another – that’s fun! Spontaneity is actually really great, it becomes an adventure. But, once again, only ask for the date spontaneously if you already really, really, really, really know the chemistry is extremely high. You know when you both have expressed how much  you really liked each other. So, you’re very confident she is going to say yes .

And that’s it! I hope that all makes sense when you’re planning your date and deciding between spontaneous or planned dates. Ask her what she’s doing this weekend, see what she’s doing, and see if you can plan something. Then, if there’s Rapport built, add some more spontaneity to add fun in the moment. Adding a mix of both dates as you continue to date is what makes it interesting, fun, and keeps the momentum going 🙂 You got this!