Dating Again In My 30s

Storytime with Kate

We're in the theme of Courage in the 2024 Self Study Program and if you've read anything about courage from us, you know that where there's courage, there's also always fear.

I've been single since I was 24. I had a longterm boyfriend from 18-24. We had known each other since we were kids. I feel in love with him the first time I met him in 8th grade at another school's dance. We talked about kids and getting married all the time. You know when people say, "when you know you know?" I knew with him. I knew how much I loved him.

He moved to Nashville for us to be together after I graduated from college.

Things were always rocky for us. He wanted to stay in our home town (lol - where I'm living now) and have babies young.

and I had to find myself. unpack her. get her out from under the rubble. play with her too.

I didn't know how to give him what he needed and get what I needed all at the same time.

After going on the first retreat Ruby ever hosted, I came home and we broke up. I knew when I knew.

He called me a year later and said, "would you be mad, happy, or sad, if I got engaged?" I had to hang up on him to throw up only to call him back to tell him that I wanted him to do what he wanted to do.

In a very perceptive way he told me, "I don't think that getting married and having babies is what you want. I think you want to want it, but I just don't think you do. 10 years from now even, if you start dating someone new, I know I'll be jealous."

The good news for him is that it's 10 years later now - and I'm still single.

I've loved my life being single. I've built businesses that MEAN something to me. I've gotten to love my life, especially my work, and get to know myself.

I joke with Ruby about the My Self Study Practice being how I've learned how to be kind to myself - I've spend 10 years learning how to listen to myself instead of him. Instead of my mother. Instead of the patriarchy.

That honestly makes me fucking furious that it's taken me this long and that kindness towards myself will be something that I have to practice, on purpose, for the rest of my life. Not furious at myself, but furious at the environment that sets us up for self-hatred, and chronically "hard on myself." Rage really. wtf?!?!

Yall got my email two weeks ago about the roots? Well sometimes what this whole process feels like is ripping a plant up by the roots and shaking off all the dirt - this part is when you feel wildly exposed and vulnerable. And then the next part of this whole thing is realizing that those roots need ground - so what kind of soil do you get? How big do you dig the hole? How much sun will you need? How close to other plants can you be? Water?!

So when I say I'm dating again what I mean is that I've been on and off the apps for a decade. I've dated a few people over the years but never in an "I'm thinking about wanting to build a life with you" kind of way.

In fact a man asked me if I would go to rooms-to-go today to help him pick out a couch and I couldn't help but burst out laughing. I said, "that was something I would have said yes to in my early 20s" because that ex and I did that. Bought a house. Picked out furniture, fixtures, lights, paints. Sold the house. Had wild sex in the kitchen that I had painted bright yellow - a pattern for me. Yes, the sex in the kitchen part and the wanting a yellow kitchen part (although, right now, my kitchen is pink - I consider it part of the whole new soil thing... pink is involved in a way that it never has been. It's feeling nourishing.)

The apps are not it for me though and I'm feeling more secure and less scarce in feeling that way. That instead of having to be discerning on an app (which as a demisexual + bisexual my options both feel wildly limited to needing an emotional connection and also completely open-ended because I don't seem to be deterred by anyone's gender), I get to be discerning in real life.

But now the barrier is: I mostly go to work, to the gym, and to home right now. My coworkers and clients are at work - all of whom I feel close to but my boundaries do NOT mix work and romance. The gym is a place for me so I'm often just in my own zone with my headphones in and my head bopping to the tunes. And at home, I'm alone there with my dog, out in the peacefulness of the country. It's serene.

And it highlights loneliness and jealousy right now.

I'm jealous that SOME other people have versions of relationships that I want.

My life has been FULL of seeing relationships that haven't made me feel jealous at ALL but I'm beginning to notice the things in some of my closest friends relationship that make me feel wildly jealous - my body going, "hey hun. we WANT that. In a big way."

So I'm taking myself on dates - I'm going on one each week. Different times of day. Different places. I'm terrified of sitting at a bar alone. So I haven't done that yet but damn I do love a $14 cocktail and I'm gonna take myself to have one in a cute outfit with a new book. Soon. I'm gonna do that soon. (narrators note: I cannot stress how terrifying this is to the writer. do not let her firey attitude and seemingly confident air about her downplay the terror of going to a restaurant alone.) I went to see a movie this past weekend - Inside Out 2. It was adorable. Never as good as the first but still totally worth seeing.

And that makes me want to note that I might be using the word jealousy when I really mean envy in this email... they're different emotions. but I sure do get them confused and jumbled.

Google AI says: "Although many people consider “envy” and “jealousy” synonymous, they actually have distinct meanings. Envy is “the painful feeling of wanting what someone else has, like attributes or possessions.” If you're jealous, you feel “threatened, protective, or fearful of losing one's position or situation to someone else.”

I guess when I feel envious I also often feen jealous. My envy often threatens a sense of self. Like, feeling envious tells me that I want connection and closeness but also brings up feelings of jealousy because I've been happily and proudly single for a decade.

WHOAH IT'S BEEN A LOT.

Anyway, do you see why this is taking a lot of courage?!

But yeah, I want to be romanced. I want to be taken out, I want to be planned for, I want to do activities that I'm often left out of "because I'm single." So I'm doing those things :)

The permission slip I wrote for myself in the 30 day "Courage is Contagious" Challenge for this month in Heartland (our online community if you don't already know! She's only $7 per month. Join me in all this?!?!) is "I give myself permission to be really uncomfortable and jealous and do it anyway."

I have my next date coming up tonight. I'm going out for a cocktail. I haven't picked the place yet so I guess you'll just have to be on the edge of your seat waiting to find out ;)

In all this I hope you hear that your jumbled mess of jealousy and envy is here to show you what you WANT. All you have to do with that information is go for it :) and you going for it (this is for the fawn-ers and people-pleasers amongst us) does NOT inherently take it away from someone else. (unless of course you're stealing shit that isn't yours... we don't do that - discernment and integrity is the name of the game). And also, you might not always get what you want. But, and I know this from DEEP EXPERIENCE, you miss 100% of the shots that you don't take. barf. I know.

I love you.

I love me.

I love Ruby.

this kind of courage is what the My Self Study Practice is designed to guide you into. 1-on-1 Self Study Coaching is a good place to start. Ruby and I are literally obsessed with doing this co-creative living-the-life-of-my-dreams work. We're on your team and there's nothing wrong with you.

i'm so glad you're here. 🧡

you're doing great,
Kate

PS Mark your calendar for Wednesday, July 10th, 6:30-8:30pm ET - We're still working on all the marketing details, so the official page and price is TBD, but if you sign up now, you can join us for just $19!  The price goes up June 26th, so RSVP to save your spot.

* if you are currently enrolled in the Self Study Program this workshop is included and you will receive the direct link to attend closer to the date

We hope to see you there!