Knowing When to Date Again

Melvin Tillman, Melvin Tillman, MA

Posted by: Melvin Tillman
Melvin Tillman, MA
267-428-2612

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After some deliberation, you made the conscious effort to stay single for some time.  Specifically, you decided to take a break from pursuing a committed relationship. Perhaps you found yourself consistently rushing into relationships, or losing part of your identity while in them.  Regardless of your personal reason, you’ve decided to take a hiatus from the dating scene. However, how do you know when you are ready to pursue a new relationship? It may initially seem intuitive (e.g., “You just know.”), but actually knowing when to date again can be quite tricky.  This becomes even more difficult due to the lure of relationships. After all, dating can be fun and exciting, but it can also obstruct your personal reasons for being single. To help you make an informed decision, this article is going to explore the ins and outs of knowing when to date again.

Understand Why You Were Single in the First Place

A primary step in knowing when to date again is to understand why you decided to be single.  These reasons vary based on the individual; however, there are some reasons that tend to reoccur.  For example, one common reason why a person decides to be single is to process their previous relationship.  Being in love with someone can be truly joyous and fulfilling; however, the end of that love can bring heartache and pain.  Healing from that wound can take time and conscious effort, which is difficult to occur within a new relationship. Imagine that you sprained your ankle while running a half-marathon, and now imagine running another one the next day.  You naturally need time to recover, and relationships are no different. However, this is simply one example for why some people want to stay single. Here are more.

  • Trying to break the cycle of being a serial dater
  • Wanting to become more comfortable with being alone
  • The desire to focus more on one’s self
  • Wanting to save money
  • Being too busy with work and other social requirements

After you’ve taken some time to identify why you wanted to be single, reflect on the progress of your goal.  If you have met your goals, that is usually a good sign that you’re ready to date again. For example, let’s say that you decided to be single to become more comfortable with being alone.  Can you confidently say that your current desire to date is independent of the anxiety of being by yourself? Essentially, you want your actions to align with your goals. To be clear, entering a relationship can be quite healthy and beneficial.  It’s simply difficult to experience these benefits if entering a relationship interferes with your personal goals.

Do a Check-In with Your Emotions

Reflecting on the progress of your goals can be challenging, and perhaps insufficient in informing your readiness to date again.  This is partly due to the multiple definitions of dating. One revolves around meeting new people, while another definition is the pursuit of a committed relationship.  Here’s an activity for the latter definition. Pick a time during the day where you tend to be in a neutral state. Specifically, this is a time where you don’t experience many stressors or emotionally stimulating events (e.g., taking a shower, getting ready for bed, riding a bus).  Following this, close your eyes and imagine what it would be like to enter a relationship. As you do this, pay close attention to your emotions. To help facilitate this emotional check-in, here are some situations to imagine yourself in.

  • Posting a picture of you and your partner on social media
  • Sharing your bed with someone else
  • Checking in with someone regularly
  • Publicly changing your relationship status
  • Emotionally supporting a new person
  • Traveling to your new partner’s place

As you imagine these different scenarios, which feelings come up?  Additionally, what is happening inside your body? Physiological sensations often reflect one’s emotional state.  For instance, quick breathing could indicate nervousness or excitement, whereas a smile usually implies happiness.  To help understand these sensations, reflect on when they usually occur, as well as what you felt during those moments (e.g., “My hands tend to shake when I’m feeling anxious, but not when I’m feeling excited.”).    While doing this activity, you may struggle to put words to what you’re feeling. If so, here’s a useful link to a feeling chart.  

Create a Pros and Cons List

It’s easy to get stuck in your head when contemplating whether to date again.  To make things easier for you, create a pros and cons list. Grab a sheet of paper, and on one side of it, write down all the reasons why entering a relationship would be beneficial.  Really focus on how your life would be different by having a new partner. Next, do the same thing on the other side: list all the deficits of ending your singlehood. After you have done that, go back and rank each answer.  For instance, if you have five items in your pros section, rank each benefit from 1-5. Ranking your answers can illuminate what you currently prioritize, which can then highlight any poor/unhealthy reasons to date again. Here’s an example to make everything clear.

Entering a New Relationship

                   Pros                                                                Cons

+Less likely to feel lonely (#3)                       -May distract from processing my relationships (#2)

+I can have sex more consistently (#5)          -Dating will take up my precious free time (#5)

+I’ll feel more confident (#2)                         -I’ll no longer be able to work on living alone (#3)

+I’ll have more emotional support (#4)          -I may be serial dating again (#1)

+Dating makes me happy (#1)                        -Dating will add stress into my life (#4)

In this example, the person may not be ready to date again.  It appears that their main motivation to date is to avoid the discomfort of being alone.  To be clear, wanting to be with someone is natural and completely understandable. However, if your goal is to be more comfortable with being by yourself, dating to avoid loneliness may not be the best.  Once again, allow your goals to inform your decision whether to date again. Besides creating a pros and cons list, here’s another concrete activity to do.

Create a Checklist on Being Prepared

When you are free from obligations and stress, take some time to define what it truly means to be prepared to date again.  Furthermore, what are the signs that will let you know that you are ready to enter another relationship? These answers can be complicated due to how personal they are, and that’s okay.  Simply reflect on the previous interventions to help inform your answers. For instance, if one has the goal of breaking their serial dating pattern, being single for six months is a good sign of progress.  Additionally, no longer feeling anxious or scared with being alone can highlight growth. Once you have reflected on these signs of progress, grab some paper and create a concrete checklist on being prepared to date again.  Here’s an example on how this can all look.

Knowing That I’m Ready to Date Again

Original Goal for Being Single: “Wanting to Break Serial Dating Habits”

  • I can go 6 months straight without being in a relationship
  • I’m no longer afraid to stay single
  • I can interact with people of my desired sex without having the pull to date them
  • I’m comfortable with doing activities on my own
  • I can rely on myself to regulate my emotions
  • I have fully processed my past relationship
  • I can decline relationship offers

Once again, this is simply one example of how this activity can look.  Regardless of what your original goal is, the more items you can check off on your list, the more likely you are prepared to date again.  To be clear, this checklist is simply to inform your decision to date again; it doesn’t have to dictate it.  In other words,  your created checklist is simply one of the many ways to know when you’re ready to date again.


Knowing when to date again is a subject that many people struggle with.  People are all unique, so there are no universal answers. Nevertheless, there are still things that you can do to figure out when you’re ready.  Reminding yourself why you were single, checking in with your emotions, and creating a checklist are all ways to guide your future, romantic decisions.  If all of this still seems too complicated, talking to someone one-on-one could help. Schedule a session with a therapist at https://www.therapyinphiladelphia.com/contact/ .