Joyconjurer Ep 5 - Release Date Anxiety


How do I ask someone out? This is someone I don't know that well. Thanks for any advice you can offer!

Disclaimer: It has been over a decade since I've asked someone out. I've never done online dating. As someone who has a long-term partner, I'd be remiss not to recognize my relative privilege in this area.

Asking someone out is an act of vulnerability. Being asked out is similarly a moment of vulnerability for the individual being approached. I don't know if the person you want to ask out is in your social circle, your favorite barista, a co-worker, or just someone you follow on social media. But starting with an awareness of the vulnerability required from both of you will ease some of the possible discomfort as you consider how to ask.

It will be easier to ask, and easier for the other person to answer, if you have a specific activity and day in mind. Choose something you think you both might enjoy. Then reach out in whatever medium you most frequently communicate. State you intention to attend, participate, or enjoy the activity on a given day and invite them to join you. Then breathe. Seriously. Nothing creates more discomfort for the other person than seeing you hold your breath (literally or figuratively) while awaiting an answer. And guess what? You did it! You just asked someone out!

Okay, I hear you. But what about the answer?

I hate to break it to you, but the answer has nothing to do with you asking. Rejection is a very real possibility, but more than likely, any rejection isn't about you. The other person could be in an emotional place where they don't want to do that kind of work, they might have enough romantic partners, or they might be content with none at all. Perhaps there's a social power dynamic at play, where the other person may not feel it socially or professionally appropriate to engage under the circumstances. My point here isn't to frighten you away, but to get you to realize that so much goes into the answer beyond whether or not you are likeable.

Rather than focus your mental and emotional energy on the response, place your energy toward the act of asking. Let asking be it's own outcome. Free yourself from the expectation of the answer, and you will mitigate many possible hurt feelings. Plus, it will similarly benefit the other person, who will feel more free to give their own answer. If they agree or offer an alternative, you can move together toward planning. If they say no or give another negative indication, accept it and thank them.

I can't caution enough against retorting. It's self-centered, pushy, and displays an imbalance between you two. It's vital to remember the agency of the other person. Consider your own life for a moment, how much you have going on under the surface, how much you are juggling, the obstacles you are navigating—not to mention your stresses or pains. The person you are asking out is going through roughly the same amount (and possibly a whole lot more). So, give both of you a break. Remember, you wanted to ask them, and the only outcome of import was to ask. Let yourself feel good for that.

TV and film do us a number of disservices. The tropes of rom-coms normalize toxic behaviors such as stalking, entitlement, and persistence as an admirable trait in courtship. They frame cishet, monogamous relationships as the standard, while othering and often ridiculing other types of romantic expression. They frequently present women as conquests or objects to be won, rather than equal partners with agency and character traits beyond "love interest." They also make it seem like there is "someone special" for everyone, that once you find your person, everything will work seamlessly. The idea of soulmates sounds romantic, but it can also preemptively let you off the hook. Relationships require work. Nobody owes you anything, even a long-term committed partner. Being a good partner means being open to growing, changing, and evolving. Negotiation is constant. No matter how much you "click" with someone, you aren't going to both be on the same page about everything all of the time.

Now, there's a whole separate article I could do about a critical, underlying question: Should I ask someone out? There's a lot of ink to spill about toxic masculinity in relation to dating and relationships, the obstacles people face in the service industry with regulars who want to cross the counter, and the unwanted (often dangerous) attention women have to deal with just for existing in the world. I'll save that for a future article, or the discussion thread for this one.

For now, I encourage you to embrace your vulnerability, be empathetic and understanding if things don't work out the way you hope, and lower the stakes in your mind. This is someone you don't know that well, after all. Keep things light, be prepared to move on/revert to your previous status quo, and don't forget to be present. Good luck!

I'd love to open this up for people to share their stories. If you'd like to post in this thread anonymously, PM me, and I'll post your comment as "anon." As always, you can also send your quandaries to [email protected].

One quick bit of additional business: Happy holidays!

I'll see you all in 2020 with the next article, and I look forward to hearing from you over the break!


Once again excellent advice. Boy, I could have used this when I was younger. I obsessed so much on my pride and ego, that I never rose to the challenge.