How Long Should You Casually Date Someone?

how long should you casually date someone

By Jackie Pilossoph, Creator and Editor-in-chief, Divorced Girl Smiling site, podcast and app, Love Essentially columnist and author

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?


It sounds like you are still healing from your divorce and not in a place to be in a serious relationship, which is completely fine. 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 you right now, and that DOES NOT mean you have 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 him. If he doesn’t understand and is still wanting sex, then it’s not the right relationship and you should break up.


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I think people put way too much pressure on themselves when it comes to sex. Having sex seems to be everyone’s biggest fear—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 relationship after divorce, and I’m so glad I did that. I had a lot of fun and learned so much.

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.


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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.


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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.

Like this article? Check out, “9 Signs of a Healthy Romantic Relationship”


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Jackie Pilossoph

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.

2 Responses to “How Long Should You Casually Date Someone?”

  1. Lena

    I just found you and tend to agree with you about first date sex. Though with the caveat that dates these days tend to be hookups. I will add that my darling ex husband (still a friend, not good for relationships) and I had sex two hours after meeting on a beach and talking each other hoarse.

    You have to feel happy with your choice and perhaps experience gives you the judgement you need.

  2. phil carey

    ive recently become seperated after 12 years i have 1 daughter 10 yers old n 2 step children who are 18 n 15 i meet my wife when the step kids were only 5 and 3 years old my daughter of 10 is the only talking and seeing x has alfeady moved a guy in since we split less than 3 weels ago im at my wits end how do i cope


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