Starting Fresh: Post-Break Up Guide

man and woman sitting at outdoor table drinking coffee

You broke up with your ex sometime ago, and you’ve gone through the grieving process and learned more about what you want in your future relationship. You’ve taken the right steps forward so that you can enter a new relationship without unprocessed baggage – and that’s an important step.

But now it’s time to take a leap and meet new people. Are you a little nervous? Don’t worry; we’ve all been in the same spot as you. In this guide, you’re going to learn how to start dating post-breakup.

You’re single, now what?

Your relationship is over, and now you’re single. Though you may feel that this is a bad thing, it’s not. Being single has many perks, and now, during the post-breakup period, you can focus on what you want out of your life.

When you’re in a relationship, it’s easy to lose sight of your needs, and now, the spotlight is on you. Now that you’re single, you have the time to think about yourself, as you should. And there are some things you need to ask yourself before moving forward.

Sex with your Ex: Yes or No?

white couple kissing in bed

Ok. I feel I should mention this because, let’s face it—many times, your ex will try to come back to you if they’re experiencing a dry spell. You guys aren’t together anymore, but you know what the sex is like, and why would you spend your time trying to get to know someone if you just want to relieve your horniness? Right? Wrong! 

I hear of men and women making the fatal mistake of sleeping with their ex-partner during the post-breakup to relieve their physical needs. But while relieving their sexual frustrations, they’re also prolonging the grieving process and hurting themselves even more.

If you really want to have sex, you can find someone else to have sex with. Going back to your ex for sex isn’t going to help you out in the long-run. So, to answer this question, no, don’t have sex with your ex. If you want to move forward with your life, leave your ex in the past, and focus on what’s really important in your future.

Identify what went wrong in your past relationships

If you want to enter the dating world with unresolved baggage, you not have the best experience. You run the risk of allowing yourself to enter a relationship that’s similar to your past ones. But that’s not what you want.

Your previous relationship ended for reasons that you don’t want to repeat. In order to prevent making the same mistakes over again, you need to understand your past relationship and identify what went wrong.

Sit down with yourself and self-reflect on your previous relationship during the post-breakup period. Write down the things you liked about the relationship and the things you didn’t like. Look at what brought you to break-up with your ex-partner. Was it a lack of communication? Cheating? A lack of respect?

Understanding your break-up’s root cause can help you see the things you need to focus on in your future relationships. So, be honest with yourself and admit to the things you need to work on during the post-breakup period. We all have things we need, and by working on your issues, you’ll be able to grow and be a better partner.

Dating after a break-up

As someone who wants to work on themselves and process the breakup, you read The Break-Up Guide and took the time to process the breakup and think about what you want in your future. Whether it took months or years to process, you feel you’re now ready to move forward.

This is a great step for you! But now, you’re thinking, “ok, what do I do now?” You were out of the dating scene for some time and forget how things work. In addition, you don’t want to make the same mistake twice and end up in a new relationship that feels a lot like your previous one. 

Focusing on the future

You’re doing your part in working on yourself and giving time to process your past relationship, which is great. And now that you feel you’re ready to date, this is a sign you’re ready to be vulnerable again and meet new people.

Go in with a positive mindset

Breakups are never easy, and when thinking about dating, it can bring up some painful past memories. But that was the past, and now, you’re looking into the future. If you want to enjoy your dating experiences, stay positive. With a positive mindset, you’ll exhibit positive behavior and energy, which increases your chances of a better dating experience. 

Take things nice and slow

When you meet someone you connect with, you get excited, and you want to spend more time with them and move things forward. But meeting the right person isn’t a race. It’s important you give yourself time to get back into dating and take things slow. Get to know the person without trying to push the relationship forward. 

Don’t focus only on dating

It’s easy to get caught up in the idea of finding someone new to be with, but dating shouldn’t be the only thing you spend your free time with. Whether your friends are setting you up with other singles or you’re on a dating app, don’t let it take over your life. Focus your time on other activities and hobbies in your life. While you’re living your life to the fullest, you’ll eventually meet someone in time. 

Reflect on what you want and don’t want in a partner

Since your last relationship has been some time, you can now look at it objectively and see what went wrong and what you liked/didn’t like. By reflecting on your past relationship, you can find a partner who’s a better fit for you. Make a list of positive and negative characteristics your ex-partner/relationship had to help remind yourself of what you want in your future. 

Don’t compare your dates to your ex

Oh, don’t do this! Comparing your dates to your ex isn’t going to do good for you. This is an unhealthy habit, and it’s one that’s very common. But if you’re comparing your dates to your ex, this is something you’ll need to break. If you want to move on truly, then you need to focus on the future and not bring your past into your dating life. 

Be realistic with your expectations

Of course, you should have a positive mindset when dating, but you shouldn’t go into a date with unrealistic expectations. This is when you run the risk of being disappointed, and you don’t need that. Don’t try to rush the experience in hopes of finding someone. It takes time to meet someone you connect with. 

Be yourself

This sounds a little cheesy, I know. But it’s extremely important to be your genuine and authentic self when dating new people. If you’re trying to be someone you think your date will like, it’s not going to work in the long-run. Always be yourself, and if it’s not a match, that’s ok. Pay attention to how you feel around this person and what your heart tells you. 

Now that you know what you need to do before going on a date, it’s important you know the conversations you need to have with a date and some interesting questions to ask when getting to know someone new. 

8 Conversations to Have With Your New Partner

It took some time, but you went through the emotional hurdles during the post-breakup, and you feel like you’re ready to move on with a new partner. If you’ve started to see someone new, that’s great, but there are some crucial conversations you need to have with them to help you understand if the relationship is right for you.

These are conversations many of us avoid talking about because we don’t want to face the possible consequences after knowing our partner’s opinions and feelings. But if you want to create a strong foundation for your new relationship, here are eight conversations you should have with them.

Work and Finances

What does money mean to you? What does money mean to your partner? By understanding the value of money in your relationship, you’ll be able to resolve conflicts around money better. Because, whether you like it or not, you most likely will go through financially tough times, but it doesn’t have to end your relationship.


Many couples experience a lack of connection after having a child. And this drop continues with each child they bring into the world. This doesn’t mean you should avoid having children to keep your relationship at the status quo. Instead, this means you need to communicate with your partner about conflict resolution and how to maintain your sexual relationship. 

Intimacy and Sex

The real difference between friendship and romantic relationships is intimacy. A deep and satisfying relationship is one where the couple can talk openly about the sex and intimacy they’re having in the relationship. It’s a hard topic to discuss, but it becomes easier with time once it’s opened. 

Relationship Conflict

It’s everyone’s dream to be in a relationship without any conflict, but what if I told you conflict can actually be good for the relationship. In every relationship, a conflict exists. We’re human; we’re all different. But having conflict in a relationship doesn’t mean your relationship is doomed.

Conflict serves a powerful purpose, and when properly understood, it can help grow the relationship and create a deeper connection between partners. Not only do you learn about yourself, but through conflict, you learn to express your feelings and work through your differences.


Commitment has changed throughout the years, and people view commitment in different ways. This isn’t good or bad; what matters is you’re both on the same page when it comes to what commitment means for your relationship. If you choose to fully commit to your partner, it means you’re accepting them for who they are, flaws, and all. 

Personal Growth

As individuals, we will grow and change. This also means our relationships are subject to change with time. However, this isn’t a change that should be feared. Instead, focus on how you and your partner will work with the change. How will you support the growth of your partner and vice versa?

Fun and Play

Relationships are work, but they’re also a lot of fun. Healthy relationships consist of adventure and fun. This doesn’t mean you both view fun and adventure in the same ways. If you both have different ways of having fun, that’s perfectly fine. What’s important is to learn how to respect each other’s ideas of fun and adventure.


We all have our own dreams and aspirations outside of our relationships. Just because you’re in a relationship doesn’t mean you need to give up your dreams. Dr. Gottman’s research has shown that relationship conflict is rooted in unfulfilled dreams. Both you and your partner should support each other’s dreams, as when they’re supported, the relationship feels more rewarding.

These are eight conversations you want to have with the person you’re seeing, but of course, you don’t necessarily have to dive right into these conversations on the first date. Here are 30 interesting questions to ask someone if you want to get to know them better.

30 Questions to Ask to Get to Know Someone Better

Do you want to get to know someone better? Well, here are 30 questions that can turn small talk into a real conversation.

  1. What’s your go-to guilty pleasure?
  2.  How do you like your coffee?
  3. What are your biggest pet peeves?
  4. Do you believe in having a “five-year plan”? If so, do you have one?
  5. How do you deal with stress?
  6. Do you want to have a family of your own?
  7. What’s the best piece of advice a family member has given you?
  8. If you want children, how do you want to raise them?
  9. Do you believe in conspiracy theories? (non-judgemental question)
  10. If you could only eat one thing for the rest of your life, what would it be?
  11. Do you have allergies?
  12. If you could change anything about yourself, would you?
  13. What’s your favorite tv show/movie?
  14. If you came back as an animal in your next life, what animal do you think you would be?
  15. There’s a puddle on the ground, do you walk around it or jump right in?
  16. Does your family go on trips together?
  17. What do you think of supernatural life? Do you believe we’re alone in the universe?
  18. How do you think your perspective has changed over the years?
  19. What’s a relationship deal-breaker for you?
  20. Which family member are you the closest to?
  21. What’s your favorite way to exercise?
  22. Pick your favorite meal: breakfast, lunch, or dinner?
  23. What’s your favorite book?
  24. How do you practice self-care?
  25. What was the best vacation you took, and why?
  26. How would you describe yourself? An introvert or an extrovert?
  27. Who was your celebrity crush growing up?
  28. What was the worst job you ever had?
  29. Do you love what you do (As a career)?
  30. Which is more important? Friends or family?

Final Thoughts

Moving forward with your life and jumping back into the dating world can feel a bit intimidating, but that’s a part of the experience. What’s important during the post-breakup is that you identify your needs before seeing new people and learn from your past relationships.


On Key

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