How to Ask for a Second Date: 10 Best Ways

Oscar Wilde once said, “be yourself; everyone else is already taken.” If only it were that easy. The minefield of how to ask for a second date in this digital age can be overwhelming. Do you text? Do you wait? Most importantly, how do you overcome your anxieties?

How long should you wait to ask for a second date?

In the world of social media, everyone looks perfect with perfect lives and perfect partners. All that comparison puts so much pressure on us to not mess up our dating lives.

So, how soon to ask for a second date?

To make things even more complicated, it’s different for everyone. Some people might hit it off such that the conversation at the end naturally finds its way to planning the second date.

For others, things might be slower and more mysterious but equally positive. In that case, a good rule of thumb for how long after the first date you can ask for the second date is usually around 2 to 3 days.

Although, how to ask for a second date isn’t about playing games or second-guessing the other person. It’s about focusing on your needs and sharing them confidently and groundedly.

This brings us to the question, “who should ask for a second date.” This one is a good debate for the traditionalists versus the modernists but at the end of the day, it shouldn’t matter.

How to ask for a second date is about what feels right for you. The key element behind this is managing your worries so you can state what you want compassionately and respectfully.

When to ask for a second date

It might seem like asking for a second date is all about timing. In some ways, yes it is. After all, if you wait for weeks, the other person will most likely have moved on.

Alternatively, calling each other the minute you’ve left might seem slightly needy. So, how to ask for a second date is about balance.

At this point, ask yourself why you want a date. Search deep inside as you explore whether this is to fill a gap in your life or if, on the other hand, you’re looking for someone to learn from and grow with.

Whether you have a traumatic past or a so-called normal one, we all carry baggage that can sometimes trigger us, especially in romance.

This can make it challenging when it comes to how to ask for a second date because our baggage tends to hold us back.

So, if you find yourself checking your phone every few minutes and unable to think about anything else, you might want to work on appreciating what you already have.

The more you can value yourself and have a balanced approach to the other areas of your life, the more likely your date will reach out to you before you consider calling.

While it’s easy to give you a rule, such as waiting for 1 to 3 days, for how to ask for a second date, the vital difference is how you ask and what drives you.

It’s all down to accepting the consequences of what you ask for.

10 best ways to ask for a second date

Remember that a grounded and secure person doesn’t base their life on who likes and doesn’t like. They simply accept reality and move on to the next.

Of course, that isn’t necessarily easy to do, so if you find yourself repeating the same patterns of unsuccessful dates and pointless relationships, help yourself and reach out to individual or couples counseling.

With that in mind, here are some tips for how to ask for a second date.

1. Manage your fear of rejection 

As a clinical psychologist explains in her article on the ego’s driving emotion, fear shapes our reality. So, instead of asking for a second date, we get lost in blaming the other person, or we are simply stuck in fear.

Our minds then get frozen in some sort of fight-flight-freeze mode and we can’t think clearly. Not only can we not pluck up the courage to call but we can’t even put a simple sentence together.

All of that happens because you don’t want to face the possibility of rejection. In other words, our fragile egos can’t deal with the idea that we might not be perfect.

Of course, rejection can happen, but how is that so bad? Only some people are meant for us, but if you reach out, you’ll never know.

If you feel your fears are holding you back, try to find individual or couples counseling. They’ll help you reconnect with yourself such that you can become more confident which, in turn, makes you more appealing.

2. Practice your message

How to ask for a second date can be less daunting if you prepare beforehand. It’s so simple to write down what you’ll say and then sleep on it.

Often, when we review these things in the morning, it’s easier to see the impact they will have on other people. We can then amend accordingly.

Then, before going on a second date, prepare yourself mentally with various relaxation techniques, as detailed in this relaxation skills guide.

3. Follow up, don’t chase 

The big question is always, “how soon to ask for a second date.” There is no perfect answer to this question because there is no such thing as perfection in this world.

What matters is that you follow up from a place of calm and confidence. If you’re needy and desperate, this will come across regardless of how long you wait before you call.

Moreover, if you’re caught up in self-doubt, you won’t be able to read the situation’s dynamics.

On the other hand, confident people act despite their fears and they support themselves with self-compassion.

4. Be assertive

Asking for a second date is about being direct and honest. If you’re trying to force things or to be someone you’re not, this will automatically put your potential date off.

The biggest hurdles to assertiveness are emotions and core beliefs. If you don’t value yourself deep down, this comes across to others who take advantage or walk away. The irony is that often, that pushes people to try even harder and appear even more clingy.

Instead, work on your assertiveness by engaging with your emotions and exploring what you believe about yourself. In other words, what does that voice in your head say to you?

To help you with this work, review this therapist assertiveness training as a starting point.

5. Find a hook 

Like great speech writers and advertisers, sometimes you need something to engage people. There’s nothing malicious about it. It’s simply a technique to connect with your potential date through a common passion.

Some people might find funny ways to ask for a second date. Others might leverage a new movie that’s just been released or a great restaurant with your date’s favorite food.

Think of it like the start of a shared hobby and you’ll naturally find something to engage in together.

6. Be specific

How to ask for a second date means being clear. This might sound obvious but our fears can unconsciously make us wishy-washy.

For example, don’t just suggest going out again. Instead, state that you’re free on Friday, for instance. You can then add that you would love their company to check out the hip new coffee shop that’s just opened.

7. Leverage existing plans 

Another great technique to take the pressure off is to use existing plans, such as attending a sports match with friends. Why not ask them to join you?

Of course, you can always use funny ways to ask for a second date and release the tension. Either way, sometimes it’s helpful to use your existing social life to make a date daunting.

Moreover, you’ll have your friends around you to support you.

8. “No” happens for a reason

We are nervous about asking someone out because rejection can feel personal. We then turn it into a general belief that we’re “awful people” and no one wants us.

At this point, it’s key to get some perspective. Remind yourself of all the great people in your life. Alternatively, make a note that you can’t please everyone. Sometimes getting a rejection can save us from a world of pain later down the line.

Things happen for a reason, and remembering this is helpful to avoid catastrophizing.

So, how to ask for a second date is about setting the mindset that this person is just another person. In other words, their response doesn’t necessarily signal the end of opportunities if things don’t go to plan.

9. Focus on the big picture 

When the phrase “should I ask him on a second date” is going round and round in your head, try to take a break. A good way to do that is to look at the other areas of your life to remind yourself of all the other ways you can find joy.

For instance, how do your hobbies, friends, family and work support you in your day-to-day life?

Another aspect of this is to work with your ego to avoid taking whatever outcome happens personally. This ego isn’t about arrogance; it’s the “I” that we all define and need to function properly.

For most of us though, the ego is a little too enthusiastic in its role. Instead, the more we can detach ourselves from “me, myself and I” and connect to what others are experiencing, the more we can open up and create deeper connections.

As this psychology article on “dropping the ego” further explains, we can get out of our ruminating thoughts and nurture a more realistic view of life.

At that point, you’ll no longer worry about how to ask for a second date. Instead, you’ll be more in touch with the dynamic you created with your date the first time. You’ll then simply know when and if it’s right to ask again.

10. Make a strengths list 

Another great exercise to build your confidence and to ask for what you want is the strengths exercise. Simply work through this strengths-use plan worksheet where you list all your positive traits.

You can then re-read the list before asking for a second date as a reminder of all the things you have to offer. With time, you’ll also build your self-esteem. Although to further help you, you might want to check in with individual or couples counseling.

Some commonly asked questions

Here are the answers to some questions that can help clarify your doubts about asking someone out on a second date:

  • How many dates count as dating?

Generally, most people seem to go for 5 or 6 dates before they consider themselves dating. Although, remember that everyone is different and the key is to check in with your date and set expectations.

  • Should you kiss on a second date?

As mentioned, how to ask for a second date isn’t about following some rules people have invented. It’s about feeling what’s right for you at the time. It’s the same regarding kissing and what things to ask on a second date.

  • What is the 3-day rule after a first date?

How to ask for a second date has been turned into a process. Although, again, do what feels right for you. Don’t try to second-guess the other person and their thoughts about going on a second date.

Although, some people swear by the three-day rule when considering how long you can ask for the second date after the first date. The idea behind the three day rule is that you don’t look desperate, but most importantly, give them a chance to miss you.

So, if you’re wondering, “should I ask him on a second date” also ask yourself, “what can I propose for a second date.” The more you plan, the less you’ll have time to worry.

  • Who should initiate the second date?

Again, don’t let other people tell you what to do, especially when it comes to who should ask for a second date.

Of course, if you’re a woman, you might read that some men like to be in charge. Nevertheless, don’t pretend you’re someone else if it isn’t your style to let that happen. This will only cause you disagreements and pain later on.

  • What are the second date rules?

A date is a connection with someone, just like any other conversation you have in your life. Every time you interact with someone, you have a choice. You can make it about you or create a positive dynamic about “us.”

So, things to ask on a second date involve being curious about them, their hobbies, friends, family and work. Similarly, share who you are and what makes you “you.”

Final takeaway

How to ask for a second date can feel daunting because of the emotions and beliefs we attach to the event. The more you value yourself and what you offer to others, the less anxiety you’ll have in asking for the date.

The inner work involved in becoming grounded and secure in our relationships takes time and often needs the help of a therapist. Nevertheless, you can help yourself with simple exercises. These include relaxation techniques, the strengths-use plan and focusing on the big picture.

Finally, how to ask for a second date is about being clear and specific. Furthermore, remember that you can leverage your friends and existing social plans to invite your date and release the tension.

Last but not least, remember that rejections aren’t the end of the world and happen for a reason. We can’t please everyone and someone else will be worth the effort.

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