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Introducing my advice column: Dear Jilla
Submit your questions on change, heartbreak and the hard stuff in life
Today, I’m introducing my new advice column, Dear Jilla. Submit your questions about change, heartbreak, healing and dealing with the hard stuff in life here, and I might answer them in a future edition of the newsletter. More on the column below.
I’ve been single for about five of the eight-and-a-half years I’ve lived in New York City. I’ve gone on dozens of dates here, most of them too unmemorable to recall, and a select few of them deeply life-affirming. Dating has always been challenging for me, and I’ve gone through a lot of heartbreak and feelings of inadequacy and longing. I still do. But I’ve never stopped trying to find love, or to further embrace my sexuality.
That’s why I volunteered to write a sex and dating advice column. For two years, I wrote Let Us Sex-plain for Time Out New York. Every week, I answered readers’ questions about sex involving toes, butt stuff, pubic hair, what virginity means, and much more. I tried my best to answer questions from a place of empathy, honesty and forceful feminism.
Advice on heartbreak I gave from three years ago feels like I could have written it yesterday:
My girlfriend and I dated for a couple months, and I was really in love with her. Earlier this month, she broke up with me. I recently went out looking for a rebound to try and help me move on, but I ended up back in my apartment crying and alone. How can I help myself, and how long should I wait before I look for someone new? I’m also reluctant to move on in case she comes back.
Aw, Kate, I know how much you’re hurting. While heartbreak feels crushingly singular in the moment, it’s universal, and you will get through this. You’re nowhere near ready to date, and any rebound you take on right now would cause you much more pain and confusion than it’s worth. Before you can begin to move on, you need to accept this woman isn’t coming back. Cut off contact with her for at least a month; trust me, the sooner you stick to this, the sooner you’ll move on. Then get busy: Pick up a new hobby, focus on doing the things you’re passionate about, and spend time with people you love. It might be a month or a year before you’re ready to date again, but just remember to be extra patient with yourself.
Years later, I’m still writing about heartbreak, love, and how we live. And I feel I have more to say directly to those who need someone to listen. So I’m starting an advice column here in CSBC: Dear Jilla.
I have no professional credentials to give anyone advice. But I am a single woman who feels both loss and hope deeply; who constantly wonders what the point of all of this is or what a good life even looks like; who doubts and fears and fails but keeps going; who’s sentimental as hell; who finds exquisite beauty and pain along the way. I know what my values are, and I believe that, for the most part, I live them. I created this newsletter to be a source of comfort and growth for myself, and for anyone else suffering and in need of a friendly mirror. I want you to look into the mirror and find the support you seek. I want to connect with you.
So, if you trust me, submit your question. Tell me about your change, heartbreak, or hardship. Make it as long as you wish; spill every detail. I will do my best to steer you toward the light, as I do with myself every day.
In late 2018, I was invited to TedxNYU to talk about what I knew about sex and dating from my experience writing the column. I used some of the takeaways from my final column about dating with intent to construct the talk. Read the full speech below:
I’ve thought a lot about dating in New York City. I was single for about five years here. I ran Time Out New York’s Undateables column for a year, which pairs people on blind dates then interviews them about their experiences, and I also authored a sex and dating advice column, Let Us Sex-plain, for two years. In my final column, I wrote about the best advice I had to offer people confused about dating in NYC, and I’ll share it with you today: Date with intent. Now, let me give you a sense of what I mean by that.
For many of us, dating is important. Like, really important. Depending on a person’s vision of their ideal future, finding “the one” can become a top priority, ahead of our careers, family, friends and interests. But have you ever stopped to think about what finding a partner is actually worth to you?
How much time is it worth to you? You have 168 hours in every week. Let’s say you spend 40 hours a week either in school or at your full-time job, or 60-80 hours if you’re trying to do both. That leaves 108 hours. Maybe you sleep six hours a night. Now you’re left with 66 hours. You still need time to commute (5 hours), shop, eat and cook (10 hours), work out (3 hours). This means you’re left with just 24 hours, or 3 hours per day, to spend on whatever you want.
How much of that time is worth it to you to devote to dating? Do you find yourself setting up dates but continually canceling them last minute, or dreading going on them at all, wishing you could just stay home to watch Game of Thrones?
Ask yourself, is it really worth your time to drag yourself to meet someone new halfheartedly? If you’re going to take time to date, date with intent.
Now, what would you hypothetically be willing to spend to find the perfect partner? $500? $5,000? More? Dating often is a financial commitment in some way, with money spent on taxis, coffee, concert tickets, and more. But there’s a whole bunch of people out there who are actually paying matchmakers to find partners for them.
In 2016 I interviewed some of the city’s top matchmaking services, and the low end price of starter packages, which usually include the outcome of at least three dates, start around $5,000. And more high-end packages, some of which guarantee you a relationship that will last at least a year, can cost $25,000 or more. If you’re thinking, well, only older, rich, desperate people would hire a matchmaker; nope! Many people in their twenties are spending this kind of money on matchmaking, including a personal friend of mine who is now engaged to her match. Some of them have very little time, but they do have some money. It’s worth it to them.
If you’re going to spend even a few dollars of your hard-earned money on dating, spend that money with intent.
No matter what you’re looking for in dating—meeting interesting people, hooking up, a marriage to last forever—the truth is that dating costs us. It costs us time, money, and, most importantly, emotional bandwidth. Any dating experience, good or bad, can stay with us for years, shaping our futures in substantial ways. A bad partner can affect our self-confidence and lead us to retreat from the people and things we love. They can make us fearful or bitter. Meanwhile, a good partner, even one you eventually part ways with, can help you reach your greatest potential. They can give you the support to create or achieve in ways you didn’t feel the confidence to do before.
The way that we date has consequences.
So use your time with intent. If you are looking for a relationship: Mindlessly swiping on the faces of strangers you’re judging within milliseconds until you run out of potential matches likely isn’t a productive use of your time. Make choices. Decide to go on one date you really care about each week, or even each month.
Incorporate dating into the things you love. If you love writing, or manga, or searching for the Hot Duck in Central Park, join a group where you have a high chance of meeting someone with similar interests. If there’s a specific experience you want to have—going to a sex party, dating someone completely different than your “type” that hasn’t served you well in the past, kissing in the rain in the West Village—you can have those things. Just search for them and ask for them with intent. And for god’s sake, stop spending time on small talk on dates. Jump right into the good stuff, like asking your date what one of his most formative life experiences was. That answer will be infinitely more interesting than talking about how unseasonably warm it is outside.
And spend your money with intent. Short on cash? Skip the six tequila sodas during which you’ll only artificially get to know someone, and instead take a free walk all the way down the West Side highway. Attend a free reading of an author you both love. Down to spend some money? Spend it on an experience both of you will be having for the very first time—going to your first burlesque show will stick out more in both of your memories than that same old dive bar you take all your dates to ever could.
Finally, love yourself above all with intent. When I wrote the sex and dating column, people wrote in asking all sorts of questions: Is he my boyfriend or not? Can long distance relationships work? How do I tell my girlfriend she smells?
But the most common question I got was: Am I normal?
The short answer is YES! Normal is nothing and everything. So many of us are so worried about different shades of the exact same problem. What feels so singular is actually so universal.
Part of loving yourself is figuring out what you’re actually looking for, and putting that out into the world in a meaningful way.
Do you know you want to be married in the next two years? Great! You’re going to take finding a life partner very seriously, and you’re definitely not going to keep seeing that person you know isn’t right for you.
Do you know you want to spend this year never sleeping in the same person’s bed twice? Cool! You’re going to make it crystal clear to the people you meet that you are not interested in a relationship, and you’re likely going to have some really weird and fun sex.
Do you feel pressure to be in a relationship but know commitment isn’t really the right thing for you right now? Okay! Face that head on and stop trying to fake yourself into dating people just for the sake of making your parents happy.
Go to therapy! Spend time alone! Be grateful for your own freedom! The type of love you’re seeking will come to you, it just may not come to you on your preferred timeline.
But no matter what you want, your intent matters. How you treat people in the world matters. And how you allow yourself to be treated matters.
So don’t let yourself down. Take a serious look at how you’ve been dating, and ask yourself if it’s fulfilling. If it’s authentic. If it’s intentional. Listen to yourself, the first time, and every time. Whatever you hear, that’s normal.
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