How to Date Again After a Hiatus or Heartbreak

It can feel challenging to know how to date again when it’s been a while. Here is the best way to jump back in.

We get it:

If it’s been a long time since you’ve been on a date, it can make you feel like you need to learn how to date again from scratch.

Especially if the reason for your hiatus was a previous heartbreak, starting over might seem like a better idea than jumping back in where you left off.

However, this article is all about how you can use your past to inform your future how to date again, without letting it impact you in a negative way.

You can do things like…

  • letting go of feelings that don’t serve you anymore,
  • setting clear and realistic goals for your next relationship, and
  • staying patient if you start to worry about when good things will happen for you.

Dust off your first-date clothes, because if you feel you’re ready to find out how to date again, then you’re ready.

Ultimately, you don’t have to learn how to date again from the very beginning. Your previous experience, even if it wasn’t optimal, is still valuable. You just have to understand how to use it!


Why is it sometimes challenging to learn how to date again?

The answer to this question may vary depending on the reason for your hiatus.

You may have…

  • taken some time to work on yourself, your career, or another life goal,
  • had a rough time with dating and decided you needed a break, or
  • gone through a breakup and needed time to heal.

These things can all affect your confidence level, your status in life, and your emotional health.

The more unresolved feelings you have about the dating experience because of your past, the more hesitation you may feel about whether you’re ready to learn how to date again.

We created this post to reassure you that it’s absolutely possible to start dating again, and your past actually makes you more likely to have success.

To reap the best results as you get back into dating, download this free ebook. It’s packed with confidence-boosting tips and ways to discover what you can do to become even more attractive to women. >> Get it here! <<

Now, let’s get started with how to date again when you’ve had a long hiatus.


Stay positive, and keep the past in the past.

No matter the reason for your hiatus from dating, you may have some hesitation about how things will go once you begin dating again.

Often, this hesitation comes from your emotions surrounding things that happened to you in the past. It may be a particular thing that happened in a previous relationship, something an ex once told you, or just your general confidence level.

The good news is, those things don’t have to (and shouldn’t!) define your future.

Everyone has challenges that they need to overcome. Once those pass, they become valuable experiences that actually make you more likely to experience success with dating, not less.

The key is to remind yourself that the past is in the past. It has already happened, and it doesn’t need to keep happening to you in your mind. You can absolutely choose to take the lessons you have learned with you as you move forward and leave all the rest.

This lesson is especially important to learn if you have the tendency to be preoccupied in comparing your present situation to your past. Not only does this make you less happy, it can also cause any woman you date to feel like you might be comparing her to an ex.


If you need help letting go of the past before you can fully embrace the future, try this:

Write down everything you can remember about the situation you’re holding onto: the good, the bad, the mundane, everything.

Jot it down in a notebook or on the computer, and then file it away for safekeeping. Put it somewhere you won’t come across very often. Try the back of a closet, in the attic, or in a locked file buried in some obscure folder on your hard drive.

That way, you are acknowledging that the past still exists and you can return to those memories anytime. You don’t have to hold them in your head anymore.

You can safely let the thoughts ease away, knowing that they’re preserved somewhere safe if you ever change your mind. This frees your mind and your heart up, like clearing space on a memory card, so you can fill them with new experiences and form new memories.


Keep your expectations and boundaries clear.

Even though heartbreak is painful, breakups teach us so much about what we do and don’t want in future relationships.

Being able to objectively evaluate your needs and enforce your boundaries are skills best learned from experience.

Even beyond that, you probably understand your expectations for yourself better, too. You know what is expected of you in relationships, things you excel at, and things that maybe you need to work on.

If you keep these things in mind as you explore how to date again, you might be surprised how you intuitively understand what you need to do.

Once you actively start going on dates again, you’ll be able to recognize much more quickly which matches have real potential for compatibility.

With expectations that have been built from experience, you’re equipped to…

  • find the best match for you in the dating pool,
  • attract her attention based on your strengths, and
  • address your challenges so you can be the best partner for her.

Sounds great, right?

The key is to keep those expectations and boundaries at the forefront of your mind as you begin to go on dates.


Don’t get caught up in the timing of things.

One of the most common questions about how to date again is the “when” factor.

You’ve taken a break, and now you’re eager to get back into dating. It may feel like it’s been a long time, and valuable months or years have slipped past, and so you want things to happen now, because you’re ready now.

However, love doesn’t work like that. (Anyone remember that Toto song, “Love isn’t always on time?”)

You may hop on a dating app and find the love of your life tomorrow. Or, it may take a year or more before you find someone you even feel like hanging out with.

That’s okay.

While we know you’re eager to jumpstart your romantic life, there’s really no time limit. You don’t lose the life lessons you’ve learned just because some more time has passed. In fact, the more time passes, in general, the more wisdom you gain.

Trust that when you do find “the one,” all this time spent looking for her was purposeful. You will have used that time to grow and become the great partner she will need you to be.


Conclusion on how to date again after a hiatus or a heartbreak:

First Date Coffee - How to Date AgainThe reason it can feel challenging to know how to date again after taking time off has to do with your feelings surrounding dating, your past, and yourself.

Happily, by…

  • allowing yourself to leave the past in the past and keep a positive mindset,
  • setting reasonable expectations and boundaries, and
  • focusing on the “what,” not the “when,”

… you can move forward into a healthy and fun dating life.


For more useful steps on building up your dating life, download our free ebook, “Why PUA Doesn’t Work for Introverts & What Works Instead.”

If you feel like your confidence could use some loving care before you get back into dating after your hiatus, check out our Magnetic Confidence program. In this four-week program, you’ll learn all about discovering what makes you awesome, setting healthy boundaries for relationships, and pursuing what you really want! Read about it here.

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Kelly from IA
Kelly is resident writer here at Introverted Alpha, which is known as the premier dating coaching company for introverted men; featured by Forbes, Business Insider, Cosmo, and more. Pick up your free copy of our 22-page ebook inside the blue box just below.

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Attracting An Amazing Girlfriend Starts With Finding Your Own Vibe.

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--> A 3-step exercise to find what makes you uniquely attractive
--> Why the “pickup artist” approach will never work for introverts and what works instead

--> How to attract women naturally being your best self

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