3 Important Questions to Ask Before a Second Date with Someone

Have you ever been in the middle of a rock and a hard place when deciding to go on a second date with someone?

Maybe you weren’t that into it or didn’t learn much.

Maybe you’re feeling needy and want to give someone more than one chance to impress you.

That’s not the end of the world. We have all been there.

What can happen is you end up in a whirlwind where dating becomes “hopeless” and “frustrating” because you did not set yourself up for success.

A way to set yourself up for success is a well-planned vetting system.

No, this is not the checklist where you create unreasonable standards, weeding out every potential option, and end up miserable and alone.

These are well-thought-out vetting systems helping you find someone who aligns with your needs, boundaries, values, and short-term plans.

Is dating exhausting? It can be. Think of everything in your life that can become draining if you don’t have a proper plan.

There are questions you can ask yourself and your prospect that will set you on a path toward improving your dating life.

As we move through this article, let’s make each other one promise. We will keep things real.

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Back to the basics

The first question we ask ourselves seems obvious, but there are more layers to it than we would like to admit to ourselves.

Do you want to know why dating sucks sometimes? No, that’s not the question.

It sucks because people do not know why they’re at the table.

The first question you should ask yourself is, why am I here?

People I talk to have similar answers to that question; I am ready to put myself back out there after a breakup, and I want to have fun, nothing serious.

Well, that’s great for you. What about the person that is sitting across from you?

I, me, and myself are not great reasons to be on the dating market.

We often have these glorious self-perceived views of ourselves and why something is great for us and our story, but we are not considering another person.

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We can unknowingly use others as a pathway to heal our wounds because it feels like what is best for us.

Take the time to answer that question. It should be easy to identify what type of relationship you are looking for.

It might feel like you did not form a bond with someone on a first date, but what if you’re the one who wasn’t ready for a connection?

F is for friends

The purpose of dating is to form a connection with someone on an intimate level, don’t get me wrong.

To form that connection, you have to enjoy that person’s company. Simple enough, right?

One thing I ask before I go on a second date is, would I be friends with this person if we weren’t dating and this was a strictly platonic relationship?

I am not telling you to strip your interest.

We get caught up in our attraction with someone, but we ignore the day-to-day lives we would live with this person if things were to progress.

Relationships can get boring, and people grow apart because they don’t have a piece of intimacy that forms long-lasting relationships.

Friendship is about sharing pieces of yourself that you would not usually release. It is about caring for each other well being. It is about shared interests and values.

I am joking, but a great friendship is as close to a relationship as you will ever get.

Asking yourself if you could be friends with the person you went on a date with will tell you everything you think about the connection you had on the first date.

The third time is a charm

Whenever a first date ends, I hope you have covered the basics; the initial questions to get to know each other and answers to some things you were curious about.

I won’t go too deep into that as it means something different to everybody.

The real courting occurs on a second or third date. You’re a bit more loose, slightly more energetic, and comfortable around the person who is no longer a stranger.

Unfortunately, you might not have that warm fuzzy feeling on the first date.

A good question to ask yourself before a second date is would I go on a third date with this person?

It might not sound like it makes sense to forego thinking about a second date and move on to the idea of a third one, but I promise you this question will give you the clarity you’re looking for.

You will think about how much energy and time you would expend if you were to go on a third date, and it would inform you about how you honestly feel about the second one.

You will think about how good your connection was on the first date and if it’s worth pursuing.

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This post was previously published on medium.com.

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