The Problem With Dating Through Big Life Transitions

You Can Date Better
5 min readMar 12, 2021


Photo credit: Reza Salehan on Unsplash

It starts off so innocently sometimes. “Well, actually… I’m not in Los Angeles quite yet.” Or maybe a more dramatic approach, stated with bold enthusiasm like, “Yeah, I basically read this book last month and it changed my life, and then I moved out, quit my job, broke up with my ex, traveled Europe for three weeks and got a dog. Not sure what’s next, but I’m never talking to my brother again.”

I don’t know what it is about making monumental shifts in our lives that drives us to use dating as an assist in this convincing-the-world-of-the-new-version-of-ourselves, but I tell ya what… it’s a thing. And I’m not just talking about the classic “rebound” situation. Whether it’s a New Year’s resolution, a hard break up, a big graduation, an upcoming move or a grand spiritual epiphany, prematurely anticipating a “new you” is a common occurrence and can wreak havoc on an unsuspecting dater existing merrily on the level — that is, someone not going through a big transition. There is a vast inequity in the current energetic storyline of these two daters. One is looking over the edge of a life cliff at dawn, filled with adrenaline and the promise of a new day, ready to parachute off, not knowing what’s below them, open to change and disruption and chaos. The other is happily seated in their chaise lounge of planning with blissful consistency and has a nice view of the sunset, finally satisfied to open up and find a complimentary piece to their comfortable arrangement.

These two daters think it’s fine at first. The parachuter is down for anything and the chaise lounger is happy to oblige. They think they know each other and themselves and they might even be falling for each other because it’s just so easy when one half doesn’t have a new life yet so they can simply define it by their current surroundings. They actually think it’s great! No, it’s awesome! It’s goddam inspiring! But doubt is a dirty, lurking beast. One of them truly needs to get to the other side of their transition first. Whoops. They weren’t ready. They were super high on life buzz and now it’s dying and it’s not working and they need time to figure it out and find themselves and WHAT THE FUCK IS GOING ON. The dream bubble pops and everyone’s soaked in soapy confusion.

Looking back at my dating history, I have a mixture of pride and regret for giving so many fellas the benefit of the doubt when I knew they were going through a big transition and I went with it anyway. Hindsight being 20/20, I do think it would have been best to get to know them, let alone get romantic with them, until after their big life transition was over and they really knew a little more about what they were ready for and wanted. Inevitably, I ended up being the stabilizer and feeling as though I was the metal pole in the ground and they were the tethered ball bouncing around my life. It’s a different beast when you’re in something with someone for a bit longer and change hits. There is history there and you’re not sacrificing as much for an unknown outcome. That has its own set of difficulties, but for our purposes here… let’s talk about the parachuters.

When I moved to Los Angeles after a sudden gut feeling epiphany, I was a total parachuter. Recently having emotionally destroyed my unsuspecting, adoring boyfriend in San Diego and carrying immense guilt over that apathetic abandonment, I stayed single for quite a while. I loved flirting but every time I tried to date, I got the feeling I was just floating on the surface of knowing what I was doing or what I wanted. I was in a new city with very little plan for making money and felt I had no business putting my instability on another person. I wasn’t me yet. This wasn’t me yet. I spent several years without any serious attachments and focused on finding some sort of path I felt good about. And it was great. Maybe not coincidentally, those are the years I created some of my strongest friendships and work connections that have sustained me through more than a decade of ups and downs.

Parachuters — stay single until you land and get some footing. Figure your shit out. Stop rushing to find proof of your newfound radicalness and instead use that enthusiasm to drive change in the bigger building blocks of life. That is, unless you’re a constant parachuter. Then you might need to find another parachuter to live that adrenaline life to the fullest, together.

Chaise loungers — I count myself among you now. Let’s be honest with our instincts of what we feel and need. As sexy and fun as it is to date parachuters all the time, if we’re looking for no drama, that is not the type of dater we seek. A common sentiment I tell people when they ask me what I look for in a person when I’m dating is that I like when I get a sense that someone feels satisfied with their life even if they don’t have everything they want right now. They can still be generous and enjoy the moment and aren’t living in a constant state of, “I’ll be happy when…” They seem to know themselves and what they want in a partner, even through heartache or when life throws a curveball. They have inner stability and are not looking for outside sources to ground them. Let the parachuters go through their transition and learn whatever lessons they need to and find a path. Maybe when the timing is right, you can find common ground without the inequity of stability.

Being in a big life transition is a cool, exciting time. I love witnessing the parachuters and wondering where they’ll land, sometimes getting to be a blip on their radar as they search for stable footing. I just know better than to date them for anything long term. When people say “timing is everything” I often think this is what they mean. Couples flourish when they’re truly ready for each other and then they can make whatever sacrifices they need to in order to make it work.

And heck, if you want to just have a wild one night stand or you’re in the mood for some fun… who am I to deny a parachuter their journey. Go forth and date, hand on the ripcord!

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Photo credit: Brenda Lai on Unsplash



You Can Date Better

Writing/content curation by Carrie Prince, founder & boss lady behind — coaching & consulting for the current online dating landscape.