Dear Life., Guest Posts, Relationships

Dear Life: Help! Dating Is Hard.

January 20, 2015


Welcome to Dear Life: An Unconventional Advice Column.*

Your questions get sent to various authors from around the world to answer (and please keep sending because I have like 567 writers that want to answer your burning questions. Click here to submit a letter or email Different writers offer their input when it comes to navigating through life’s messiness. We are “making messy okay.” Today’s letter is answered by A. Wolfe!

Send us your questions because there loads of crazy authors waiting to answer ‘em. Just kidding, they aren’t crazy.

Well okay, maybe a little. Aren’t we all? xo, Jen Pastiloff, Crazy Beauty Hunter. ps, I will see you in London Feb 14th!! Only 5 spots left!


Dear Life,

I don’t mean to brag, but I’m a pretty cool person. Well, maybe not “cool,” I’ve never been cool (other than for a few inexplicable months in second grade), but I have a lot to offer the world, as a worker, as a thinker, as a friend, as a girlfriend.

The girlfriend part is hypothetical; I’ve never really had a boyfriend. I think I could be a pretty good girlfriend, accounting for a learning curve. And I’ll admit, I don’t come across this brashly in real life, there’s just something about writing that gives me confidence. The point is, I’m a good person, and I think I’d be a good girlfriend. But I’m just terrible at meeting guys! I find myself accidentally leading more and more towards a monastic lifestyle. I work from home, and when I go out for dinner or whatever, I’m usually catching up with a friend and focusing on them, not on trying to flirt with boys. I’ve tried online dating, but I’m not really in an online dating “mood” right now (and I definitely need to be in the right mood for it).

I’m at peace with being single, don’t get me wrong, but I’d like to try having a boyfriend for a bit. In my 23 years on this planet, I’ve occasionally gotten close to a relationship, but never quite reached that point. But please, life, give me the kick in the butt I need to get out there and meet some boys! And some how-to tips would be most appreciated.


Jen Pastiloff is the founder of The Manifest-Station. Join her in Tuscany for her annual Manifestation Retreat. Click the Tuscan hills above. No yoga experience required. Only requirement: Just be a human being.

Jen Pastiloff is the founder of The Manifest-Station. Join her in Tuscany for her annual Manifestation Retreat. Click the Tuscan hills above. No yoga experience required. Only requirement: Just be a human being.

Dear K.,

Dating is hard. About one-third of the workforce is now freelance with many working from home like you are, making meeting people that much more difficult. So you’re definitely not alone. You’re not alone in being completely comfortable and content not being in a relationship, either. But, like many people, being comfortable alone also means overcoming inertia, and this will be your main goal.

The good news is your dedication to friends and career means you’ve already checked some important things off the to-do list, but the truth is that dating and getting yourself into a position to date takes so so much work, especially if you’re fighting inertia. Unfortunately, you are a victim of our new cultural habits, because the physical disconnect we’ve acquired either from working at home or staying connected almost solely through social media—especially in the past five years, the years when a person your age would be venturing into their first serious relationships—has warranted that meeting people in real life requires serious work.

Think of it like this.

A person’s world can be divided into fours: family, friends, career, and romantic love. These are the absolute most important elements to every person’s life, some less equal than others. Each one has its own obstacles, but you’ve probably heard the saying that nothing worthwhile ever comes easy. Let’s say you decide you want a fellowship. Once you say you want that fellowship, wouldn’t you immediately work your ass off day and night to get it? But let’s say you decide you want to be in a relationship. Despite romantic love being one of those four parts of a whole life, we are often not willing to put that same work into getting our desired outcome, or more likely are afraid to admit that it might be something we really, really want or even need. Because…is that weakness?

I don’t think we’re totally sure anymore. I mean, it almost sounds disgusting writing it, kind of sleazy like reality dating shows breeding Bridezilla women who only focus on getting a man in their lives. This might be the reason we feel the need to preface our requests for love with the proclamation that we are completely comfortable being alone. I see it often. I’ve even done it myself. Maybe I was afraid the romantic love part wouldn’t work out, so I omitted it. But wouldn’t it be nice if our comfort being alone was just a given, and we didn’t have to justify our wanting romantic love? I wanted romantic love simply because I wanted it, and I know I had to come to terms with its importance in my life.

So my advice to you firstly is to recognize that the time and effort you’re putting into being out with a friend and keeping sincere eye contact is so so admirable. But the reality is that when you find a relationship or get into a relationship, you will no doubt be adding a new textural layer to your life, and it will require a great deal of your time and energy, even if you are an independent, free thinker. This will sound like the lamest, most anti-feminist thing in the world, but you may have to sacrifice bits and pieces of your friend relationships when you get into a romantic relationship. And you will feel weird about it until you feel a little less weird. Men have to do this, too, but it’s a necessary period of adjustment to get ready for a worthy addition to your life that will take time and energy.

I’m not saying to crassly ditch your friends and flash strangers in a bar. Please don’t get me wrong. But I am saying that you need to open up yourself and your time for someone. That means, for instance, having some kind of occasional pact in place with your friends for when you go out, so that if someone catches your eye, you will feel free to divert your attention to them and not feel as though you are a terrible person. You? If you’re as good a friend as it seems, your friends will probably understand. You’ve earned it. This won’t be an all-the-time thing, but they’ll trust you when your eyes wander that you’re not being insensitive. We have come a long way in regenerating our deep female friendships. It’s fantastic. But I think those friendships can occasionally become a crutch to us when we are afraid of the consequences with the romantic world.

I once went out with a friend who was single and looking. We sat at the bar—where people sit if they want to mingle—and a handsome man politely excused himself before leaning between us to pick up his drink. He smiled wide, friendly, directly at my friend, and my friend—who literally just told me she is ready to get into a relationship—completely ignored him. I mentioned that the guy was trying to flirt with her, and she said, “What guy?” It seemed my friend was ready to get into a relationship but had disconnected herself from the daily interactions that lead to such relationships.

Not every interaction has to lead to a flirting session and to a relationship. It’s difficult to be a single-and-looking heterosexual woman right now, because you’re bombarded by things like catcalling and want to just shut down after so much uninvited male attention. But being aware of others, recognizing respectful approaches, and engaging in flirting is still good practice. And remember, practice helps break inertia. Yes, sometimes you might get a guy who is creeping a little too much, and you’ll have to do the fancy footwork with your friend’s help to get out of it. But you might also meet a nice and respectful person to chat with for a few minutes. The alternative is to take control and be the flirting instigator. I met my partner by walking up to him and asserting, “I’m supposed to know you.” Turns out we had the same sense of humor, and he thought I was funny. I have, however, been shot down with my approaches before, but you have to try.

Now I will get into the practical advice of dating. Online dating is fine. I even know a few marriages that have come from OkCupid, but that’s not what I’ll be focusing on in this, as it seems you’re longing for a face-to-face connection. And I have some good news for you. Like, really really good news. Because the absolute best way to meet someone in real life is to do so through a creative connection.

You are a writer. Maybe even an artist of another sort. My suspicion is that you would find yourself happy with someone else who displays a creative outlet, even if they’re not doing it for a career. So my best piece of advice is to put yourself out there creatively to find a venue to meet men. In every city, there are readings, art shows, performance series, microcinemas, and multi-media whathaveyou’s. You need to not only be going to these places and events but participating in them.

Let’s say there’s a local reading series, and you go to one of these events, then introduce yourself to the organizer. If you get to read one of your pieces at the next event, especially if it’s a personal one, you will already be opening yourself up to people in the room. It’s like an invitation: I’m sharing myself, and I’m open, so please come and talk to me. And if someone’s at a reading series, then they’re already interested in writing, and you already have a solid shared interest. Better than attending someone else’s event is throwing your own.

Approach a local bookstore or bar with an idea for a quarterly reading and performance series. Hit up all your friends for possible artists to participate, and when the big night comes, understand that while this is also just a really rad thing you’re doing for yourself, it’s actually an opportunity. You are the debutante, and this is your ball, and you are essentially introducing a crowd to your aesthetic and interests. I can’t think of another way to break the ice better than showcasing your talents. Sure, it’s going to be work. But like I said above…inertia.

As an example, I once started a band with my best friend because I wanted to purge myself of an old relationship and meet new people who might “see” who I was through my creative pursuits and approach me if they liked what I was doing. Your creative output is “You,” and it is a far better representation than any online dating profile. I ended up meeting a guy who wanted to listen to records with me all night, and even though the relationship didn’t ultimately work out, I had a beautiful three-month patch to stitch in my quilt, and it reminds me of how vast the world of loving can be. It’s also one of several necessary relationships I had that trained me for the one I’m in now.

The next idea is to take a class or a workshop, something outside of your comfort zone, preferably a type of class where men will be present, which may not be pottery or jewelry making. In my city, we have a fun arts/science/technology space that offers affordable classes in things like circuit bending or picking locks. And when I look in the window during one of their classes, I see like fifteen men having fun learning a new skill. Ever wonder why college friendships are so deep? Well, your brain is actively expanding while you’re learning, and you are bonding with your peers through a shared experience of struggle/triumph. If you want to meet someone engaged with the world, someone who’s open to growth, that person will be the kind of person who takes a class for fun, just because he can. And he might also be able to turn your old Nintendo into a synthesizer, but then, so would you after your circuit-bending class. On top of meeting men, you’ll be broadening your skill set, which is attractive in any person.

I will admit now that teaching myself to repair old Caliphone record players was fun and aligned with my interests, but I was also kind of trying to impress men. It sounds gross at first, but in the doing of it, I also grew to love the inner workings of belt-driven simple machines. Also keep in mind that you’d probably want your men to impress you, too, maybe by taking a sewing class, so it does go both ways.

Now, when you get to these readings or workshops or museum talks or running groups or archery lessons—or let’s say you were already going to these things and you still weren’t meeting men—the next step in breaking inertia is to take a big slow breath and look deeply at the people around you. Study them with fascination. These are complex organisms with blood and bone and a past, and they are so awe-inspiring just for even being able to walk and talk, and if you start treating others as though you are a tourist in the human race, you might find yourself more engaged and more connected with the people around you. Be fascinated by small things for one day, and speak aloud the things that fascinate you. Are you learning how to pick a lock, and it strikes you that the design of this lock is so simple and elegant that we’ve been using it for hundreds of years with very little change? Turn to your neighbor and say so. If they are a wet fish, maybe they will shrug. But if they are a warm-blooded human like you, they will respond with their own curious thoughts. Even though I’m in a long-term relationship, I still use this technique with my partner. I want to reset my brain and remember his depth. As whole and round and endless your thoughts are, his will be just as enormous as yours, in different ways.

Next: ask questions. (You’ve heard of the “36 Questions”? This is their application.) As women, we were taught to ask questions and show interest in men in bad ways, ways that neglected our own needs. But to show that you are open to relationships and possibilities, you must ask questions and be curious. You want your potential mate to ask questions of you, right? Again, it must go both ways. I once met a guy at a party who was a mapmaker. I don’t know much about maps, but I thought they were beautiful, and I asked him what he thought about topographic maps, because when I imagine a map in my head, it’s a map with directions, not geographic complexities. Turns out, he had a lot of thoughts on topographic maps, and zero people had ever asked him about it. We were drunk, you know, so he might not even remember the conversation, but it made enough of an impression that we exchanged contact information and ended up seeing each other for a very pleasant few months. He was always very good about asking me questions in return, but if you find yourself in the one-sided-convo trap, I have a technique for this, too. Wait for a lull in the conversation, smile, tilt your head, and say, “What would you like to know about me?” It’s a pointed, confident question, presented in a way that invites a playfulness without shutting down the conversation. Essentially, it’s an invitation. And it works. Speaking of invitations…

I live in a city where people go to house parties more than they go to bars. It’s prohibitively expensive to drink at a bar here. But in terms of meeting men and dating, it is not advisable usually to meet someone at a bar, because there’s no context for your meeting outside of alcohol and neighborhood convenience. (“Cool, so you enjoy getting drunk and not venturing out too far from home? Me, too.”) Parties are where you will meet vetted acquaintances, and having people in common is actually pretty important, because the one thing people don’t tell you about dating is that no matter what turns you on or what kinds of qualities you’re looking for, you are actually looking for “family.” By this I mean you really want someone who has the same playfulness, the same arguing style, the same timing as you, and these are all qualities you’ve gleaned from your real family. You’ve already picked your friends because you feel a kinship with them. It is natural to want to find a member of their extended friend family. So, you need to urge your more social friends to throw parties or invite you to ones they know about.

Verbally express this interest to them. Offer to help plan a cocktail party or something that requires minimal participation but is still fun. My favorite suggestion is to plan a party where everyone brings their favorite record or cassette, and people jump in and DJ the party with their music. Or, another successful party idea is everyone coming ready to play the most embarrassing song they have on their mp3 player. It’s a humbling, fun experience, but you can bond with strangers over their shared terrible taste in music. The key to the successful party to meet people lies in the participation of your friends. Get your people on board, let them know you’re ready to start putting in the work of meeting new people and expanding your social circles. You don’t meet men in a vacuum. You meet them in the middle of your healthy and robust friendships. I met my partner when our respective best friends got married, and it knocked me off my feet, because the atmosphere was already swirling with love and fun and friendship, amplifying the connection. So really, what I’m saying is…

Have fun. Surround yourself with so much love and friendship in a single room that you can’t help but be your true self, and with that outward confidence, be fascinated by the people you don’t know already, let them know you want to know them, and then just see what happens. The risk might be worth that reward. Even if none of these suggestions works out, you will have really tried and broken your inertia, making it that much easier when you do meet someone to approach them with open arms, ready for what’s next.

About A. Wolfe: 

A Wolfe is a writer and filmmaker in Los Angeles. A 2014 A Public Space Emerging Writer fellow, you can find her work in The Pinch, Quarterly West, The Collagist, Vice, Flaunt, Bullett, and other publications. Visit her at
She tweets at @AWolfeful.

*Please note: Advice given in Dear Life is not meant to take the place of therapy or any other professional advice. The opinions or views offered by columnists are not intended to treat or diagnose; nor are they meant to replace the treatment and care that you may be receiving from a licensed physician or mental health professional. Columnists acting on behalf of Dear Life are not responsible for the outcome or results of following their advice in any given situation.

Join Jen Pastiloff, the founder of The Manifest-Station, in The Berkshires of Western Massachusetts in Feb of 2015 for a weekend on being human. It involves writing and some yoga. In a word: it's magical.

Join Jen Pastiloff, the founder of The Manifest-Station, in The Berkshires of Western Massachusetts in Feb of 2015 for a weekend on being human. It involves writing and some yoga. In a word: it’s magical.

Join Jen Pastiloff in Atlanta March 8th. Click the photo above.

Join Jen Pastiloff in Atlanta March 8th. Click the photo above.

The Manifestation Workshop in Princeton, NJ April 11! Only requirement: be a human being. Have a heart. Bring a journal.

The Manifestation Workshop in Princeton, NJ April 11! Only requirement: be a human being. Have a heart. Bring a journal.

Featured image: by Salmando

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