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

casual dating to serious relationship

By Jackie Pilossoph, Founder, Divorced Girl Smiling, the place to find trusted, vetted divorce professionals, a podcast, website and mobile app.

Going from casual dating to a serious relationship is a huge transition. It might seem scary or uncomfortable, which is understandable. But I will say, it can also have so many wonderful benefits!

I received this email from a reader:

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. Casual dating to a serious relationship is terrifying for me, even though I love this woman.

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.”


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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, and makes you feel lonely and hopeless. 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 in going from casual dating to serious relationship?” 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, maybe even insecure. You now have a lot to lose. Although scary to put yourself out there and risk being hurt, isn’t it wonderful to have something so special that you don’t want to lose it? Try to see it in a positive way. Embrace it, celebrate it. This is what you’ve been waiting for!



2. This is tricky. Unlike casual dating, serious relationships can be work, at times. Girlfriends can nag. Boyfriends can get complacent. It’s not a bad thing, it’s just reality. Ask yourself, “Am I up for this?” It’s not always going to be rosy. Being in a serious relationship means being there for everything: not just romantic dinner dates and good sex. It means dealing with each other’s families, her cat, her complaints. He might drive you crazy at times. That’s all part of being committed. But being committed is wonderful too!

3. Perhaps the biggest change going from casual dating to serious relationship is the best one: You’re going to experience indescribable happiness. In the right situation, there is nothing more fulfilling, joyous, breathtaking and meaningful than connecting with someone in every possible way. So, forget figuring out if you can “handle it.” Instead, enjoy it! You’re about to embrace the newness of giving yourself to this person and receiving her love in return. That to me means a heck of a lot more than polite dinner conversation, flirting, good night kisses at the door, and wondering if he or she will text you for a second date.

In closing, the key to going from casual dating to being in a relationship is realizing that love isn’t always perfect, and with the bliss comes many imperfections that might seem overwhelming at times. But, I’ll leave you with a quote that should answer your question, “Can I handle it?” It’s from the classic film, “Casablanca.”

“Kiss me as if it were the last time.”

Words like these are reserved only for true love. They aren’t what you hear on a casual date. Who wouldn’t want to handle that?

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


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    Jackie Pilossoph

    Editor-in-chief: Jackie Pilossoph

    Jackie Pilossoph is the Founder of Divorced Girl Smiling, the media company that connects people facing with divorce to trusted, vetted divorce professionals. Pilossoph is a former NBC affiliate television journalist and Chicago Tribune/Pioneer Press features reporter. Her syndicated column, Love Essentially was published in the Chicago Tribune/Pioneer Press and Tribune owned publications for 7 1/2 years. Pilossoph holds a Masters degree in journalism from Boston University. Learn more at: DivorcedGirlSmiling.com

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