created at: 2013-08-20I haven’t dated around since 2008. But when I was dating, I was really into it. I loved dating. I loved meeting new people and figuring out how I wanted to connect with them and what it felt like to hang out with them. I wanted to find different ways in which we might enjoy each other. Casually dating multiple people meant that each person could fit into my life in a different way, with a different mood or different perspective.

In planning this series about teshuvah (repentance) and reflection in sex/dating/relationships for the month of Elul (see the first and second posts), I asked friends what they thought about teshuvah in their dating lives. Many people shared that one of their biggest regrets in dating was being inadvertently hurtful to potential partners. For example, how do you treat someone you cease to be interested in?

What is owed to them as a courtesy, and what is better left unsaid? Is it nicer to respond to a message from someone online by saying you’re not interested, or is it kinder to ignore it? Is it nicer to tell someone you went out with that you’re not interested, or is it easier just to not follow up? While you’re still figuring out where you’re at with someone new, how do you communicate about being a little interested but not sure?

In the past two weeks I’ve talked about transformation—shifting from how we think we should relate to one another toward how we make room for authentically relating to one another. This year I’ve had a simple chant that has challenged me to take some big risks in transforming my relationships: More honesty; less anxiety.

More honesty; less anxiety. Say what you feel. Say what you want. Say what you need. Find a way to understand your own feelings and own up to those feelings. Communicate your feelings to another person in a way that doesn’t demand the other person immediately succumb to your needs, but rather gives the other person the information that will help them best determine how to treat you. Assume that other people—particularly friends and dating partners—really want to treat you well and that they just need all the information required to do that. And only you have that information.

Instead of asking what the “nicer” thing to do is, I invite you to ask yourself what the more honest thing to do is. If you’re not interested, say you’re not interested. If you are interested, say that! Connect through honesty. If you know you want some parts of a dating relationship but you don’t know if you want some of the other parts, that’s OK too. Honesty becomes a lot easier when you’re not trying to shove yourself into a standard type of relationship that absolutely cannot work for everyone all the time. You don’t have to fit your relationship into a mold. Get to know another person and communicate about how you each feel, what you want and what you need, and figure out if there’s a way in which you can be positive presences in each other’s lives and enjoy each other’s company. That may mean a friendship, or casually dating, or hooking up, or long-term committed monogamy, or long-term committed polyamory, or something else entirely. I don’t know. And you don’t know either until you meet that person. Your connection with each person may be different.

By speaking up honestly, you can commit to both taking care of yourself and working to respect the other person as an individual capable of taking care of themself within the reality of your relationship (or non-relationship, as the case may be).

And so, I apologize for the times when I didn’t speak up, for the times when I tried to be nice instead of being real. I’m sorry for when the words that expressed what I was honestly feeling got swallowed by the waves of anxiety regarding what I should have been feeling. I’m sorry for having tried to fit our connection into a pre-existing mold that I thought was expected and appropriate instead of figuring out collaboratively what actually made sense for both of us. Let’s try again. Let’s figure it out.