Is It a Good Time to Begin Dating?

What does it mean to be ready? The case of Olivia Wilde.

Posted Nov 30, 2020

S_Bukley on Shutterstock
Source: S_Bukley on Shutterstock

Anyone who has been through a breakup knows how hard it is to get back out into the world of dating and begin again. There are so many questions: Am I ready? What should I keep in mind as I open myself back up to someone new? How long should I wait?

Actors Olivia Wilde and Jason Sudeikis recently announced they are breaking their engagement after spending nine years together and having two children. According to sources, they both say there was no drama, they simply grew apart and struggled to maintain their bicoastal life together.

Who knows when either of them will be ready to meet someone new, but Wilde spoke openly about meeting Sudeikis years ago, before she expected to be ready to get serious again. “I was just learning to be by myself,” the actress told Marie Claire in 2013. “I’d been divorced for nine months. We were both seeing people but were single. He seemed to really see me, see through the bulls–t.”

It sounds as though she wasn’t actively looking to get involved with someone new, but he caught her attention. So, how can you know when the time is right, and what can you do to prepare so that you can give your new relationship the best shot possible?

After a heartbreak, filling your calendar with hopeful connections often seems like a positive step, keeping you from being consumed with  recent loss and the emptiness that typically follows. However, it can be a good idea to give yourself time to cleanse your palate, so to speak, before jumping in to a new relationship.

It is hard to walk away from a relationship that has ended without believing that you or your partner did something wrong. Depending on which one of you ended things,the breakup can affect you in different ways. If your partner was the one to call it quits and say goodbye, your self-esteem may have taken a hit, in which case it is important to find ways to feel good about yourself before embarking on the quest for new love. That might involve surrounding yourself with family and friends who help bring out your best or taking up an activity that boosts you. The point is to spend time with people and do things that make you feel valued and supported, allowing you to rebuild your confidence.

If, on the other hand, you were the one who ended it, you might be consumed with guilt. If that is where you find yourself, it might be good to allow a little time to ease your burden. Take the opportunity to develop a clear sense of direction. In other words, now that you have some idea of what didn’t work for you in a romantic relationship, it might be easier to figure out what you need from someone so that it will work.

As you proceed, you can either try to find a version of what you had in your last relationship or you can explorer being with someone completely different and experiencing something new. You want to avoid going out with someone while you are still steeped in feelings of sadness and inadequacy.

Two risks can arise from reentering the dating world too soon. The first is talking to your new romantic interest about your ex, which can be a real turnoff, since it signals your unavailability to begin a new relationship. The more distance you have from your breakup, the less likely you are to share too much about your past relationship.

The other risk is that talking about your ex could lead your new partner to think they are being compared to your old partner and fear not measuring up. In fact, without realizing it, you may be comparing everyone you meet to your previous partner and failing to give yourself a chance to get to know the people you are meeting.

There is no set timeline for getting back out there. Everyone deals with it in different ways. For some, it could be immediately or just a few weeks, for others it could be months.

However, it is always important to look toward the future. As Wilde said, when she first met Sudeikis, her impression was that she was able to be herself with him. After that, they had nine good years together. The key is being able to be authentic with the person you are dating, no matter when you meet each other.