Going From Casual Dating to Serious Relationship-Can You Handle It?

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

casual dating to serious relationship

Going from casual dating to serious relationship is a huge transition, with too many benefits to possibly count. In this week’s Love Essentially, published in Chicago Tribune Pioneer Press, I respond to a reader in that situation, in which he asks, “Can I handle it?” 


Can I Handle Being a Boyfriend? By Jackie Pilossoph

Jackie, I recently went from casually seeing someone to officially being her boyfriend. I’m wondering what’s going to change and if I can handle it.

Love is a funny thing. If you’re looking for it and you feel ready, chances are you won’t find it. You’ll be frustrated and sad and have a sense of loneliness or maybe hopelessness. Yet, almost always when you aren’t looking for love or expecting it, it sneaks up on you. Why is that? The only possible explanation I can think of is, perhaps love’s unpredictability is meant to help us feel even more gratitude for such a powerful gift.

Not everyone agrees with me, but I think that people go on dates because they are looking for love. You can fool others or fool yourself and say you are dating just for fun, or for sex, or just to meet interesting people, or to get over your ex, or many other reasons. Ultimately, even if we want those things, we want love, too, which is the real reason we put ourselves in the dating pool.

There are several outcomes of casually dating. Ever have a string of really bad dates that makes you say, “Enough. I need a break.” That recently happened to one of my girlfriends, who declared she was taking a “mancation.”

Then there’s the dry spell, which I personally hate. I have gone through times in my life when I wanted to go on dates and felt like I couldn’t get one to save my life. It’s awful. The good thing about dry spells is, they always come to an end.
That leaves the last outcome of casually dating: you meet someone, you start developing strong feelings for the person, decide you don’t want to date anyone else, and then it hits you: you realize you’re in love. It’s both incredibly scary and the best feeling in the world. Maybe you wanted it, maybe you didn’t. Either way, you’ve got it and you’ve got it bad.


To answer your question, “What’s going to change?” Here are three things:

1. When you were casually dating, it was fun, it was harmless, and honestly, it was safe. Now your relationship is fun, minus harmless and safe. Now you feel like you have something to lose. You might get hurt. You might feel vulnerable, shaky and frantic. These emotions are frightening, but I think they are normal, wonderful feelings that should be embraced and celebrated–not feared or looked at in a negative way.

2. This is tricky. Unlike casual dating…Click here to read the rest of the article, published in Chicago Tribune Pioneer Press. #3 is my favorite!
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Jackie Pilossoph

Editor-in-chief: Jackie Pilossoph

Divorce is a journey. Live it with grace, courage and gratitude. Peace and joy are on the way! Jackie Pilossoph is the creator and Editor-In-Chief of Divorced Girl Smiling. 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.

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