How Long Should You Casually Date Someone

A Divorced Girl Smiling reader wrote this: I am recently divorced and not sure I want to get into another relationship right away, but don’t want to sleep around either. Is casual dating without sex even possible? And, how long should you casually date someone before they expect it to be more?

 How long should you casually date someone?

It sounds like this woman is still healing from her divorce and not in a place to be in a serious relationship, which is completely understandable. Divorce is a huge life transition, and it can take months or even years before you are ready to get into a deep, meaningful relationship.

Casual dating is actually a great idea for this woman right now, and that DOES NOT mean she has to have sex! It IS possible to date and not have sex, and if someone you are dating is pressuring you to sleep together, then you should talk about it with the person. If he/she doesn’t understand and is still wanting sex, then it’s not the right relationship and you should break up.

I think people put way too much pressure on themselves when it comes to sex. Having sex seems to be a big fear—for men and women in dating after divorce, which is understandable because it is a vulnerable, scary time where self-esteem isn’t at its best. So, take your time with sex and seriousness.

I love the idea of recently divorced people dating casually. It’s a wonderful time to get to know yourself again, and figure out what you want in a partner this time around. The more you date (casually) the more you get a sense of what and who make you happy. You also become wiser, you are better at reading red flags, and you learn how to have fun more, and not focus on the pressure of finding husband #2.

I dated a lot of men casually before getting into a a serious relationship after divorce, and I’m so glad I did that. I had a lot of fun and learned so much. Yes, it did come with disappointments, tears, and frustration, at times, but in dating–before or after divorce, that comes with the territory.

So, how long should you casually date someone?

When it comes to how long you should casually date someone, there are no rules. A couple can casually date for months, even years or forever. It all depends on the expectations each person has and what each one wants. If casual works for both, that’s wonderful. But, if one person in the relationship wants more, that’s when issues and conflict might start to come up.

Let’s break this down into two scenarios:

1. You are the one who is ready to go from casual to serious.

It can feel very frustrating when you are dating someone who wants the relationship to stay friendly and fun, and you feel like you’re falling in love and want more. It can feel hurtful and sad and you can start resenting the person. My advice is to talk with the person you are dating and tell him or her how you feel. Then at least you can say you tried. The person will either want to give the serious relationship a shot, or they will say they aren’t ready, and/or that you aren’t the one. That can feel devastating, but at least you know, and you can move on and try to meet someone else who wants what you want.

2. The person you are dating wants to go from casual to serious.

This can make someone feel very guilty and sad. You feel a tremendous amount of pressure, like you are doing something wrong, like maybe you led the person on and now he/she wants to take it to another level and you don’t. I think you owe it to yourself to be completely honest and tell the person how you feel, that it just doesn’t feel right right now, that either you aren’t in a place to be in a serious relationship or that he/she isn’t the right person. You will probably feel immensely relieved if you are upfront and honest. Plus, you are doing the person a favor by setting them free to find someone who wants what they want.

Neither of these scenarios are easy, and someone will get hurt if two people want different things. But that’s all part of dating. Remember, that when it comes to how long you should casually date someone, there is no right or wrong answer. Just be happy, be honest with yourself, and be honest with the person you are casually dating. You are divorced and have already been through so much. It’s time to be selfish and be true to yourself.

You will know when it’s time to take your casual relationship to a serious one. If you aren’t sure, that means you’re not ready.

Editor-in-chief: Jackie Pilossoph

Divorced Girl Smiling is here to empower, connect and inspire you. Jackie Pilossoph is the creator and Editor-In-Chief of Divorced Girl Smiling, the site, the podcast and the app. A former television journalist and newspaper features reporter, Pilossoph is also the author of four novels and the writer of her weekly relationship column, Love Essentially. Pilossoph holds a Masters degree in journalism and lives in Chicago with her two teenagers.

The author of the novels, Divorced Girl Smiling and Free Gift With Purchase, Pilossoph also writes the weekly dating and relationships advice column, “Love Essentially”, published in the Chicago Tribune Pioneer Press and the Chicago Tribune online. Additionally, she is a Huffington Post contributor. Pilossoph holds a Masters degree in journalism from Boston University.