Everything I Know About Dating

Anne Lamott is a gem. On her 61st birthday, she shared everything she knows at this stage of life — a virtual treasure trove of wisdom…

Laughter really is carbonated holiness.

Everyone is screwed up, broken, clingy, and scared, even the people who seem to have it more or less together…So try not to compare your insides to their outsides.

Earth is Forgiveness School.

Yes. Yes. And YES.

Inspired by Anne’s honesty and spot-on humanness, here is everything I know about dating. I don’t derive my expertise from an MFT license or a sociology degree — my knowledge is the result of the hard, grueling work of dating as a 20-something in San Francisco. From the confusing rules of dating here to the overwhelming number of online platforms, this city provides ample training ground for figuring out what it means to date well.

So, here are my pearls. I hope they help.

1. Dating is a constant lesson in vulnerability. There is no closeness without risk. This is both the awesome and impossibly hard thing about relationships. You have to bare little pieces of yourself to the other person as you get closer — otherwise, you won’t. And to get a date in the first place, you’re going to have to put yourself out there. Be open to blind dates, try a dating app, ask your married friends for advice, and just be open to people who don’t fit your usual “dating profile.”
2. Don’t go too deep too fast. I’ve learned this the hard way. Whether you share too much too soon or someone is trying to get too close to you too fast, it just doesn’t work. So, repeat this one with me: take your time.
3. Don’t be discouraged if things aren’t clicking right away. Just because you’re finally “in a relationship” doesn’t mean you’ll suddenly feel perfectly comfortable with this person. I am so guilty of this. I want to go from “hi, nice to meet you” to cooking dinner together or just sitting in silence reading our own books side-by-side because we’re just that comfortable with each other. Unfortunately (and fortunately), that’s not how dating works. These days I’m learning to appreciate all the different stages of relationships — from the early butterflies to the comfortable nights being “alone together.” They’re all valuable in their own ways.
4. Don’t expect your relationship to lead to marriage. Enter with expectations of learning and growing and changing, and you’ll find those are much more easily met than specific end-goals like marriage and babies and happily ever after. Because the truth is that unless you marry that person, you’re going to break up. That probably sounds more pessimistic than I’m intending it to; what I really want to share with you is that’s 100% okay for a relationship to end. It can be good! Because it’s true what they say: you’re closer to finding your spouse when you’re single than when you’re dating someone that’s not right for you.
5. Speaking of happily ever after, dating and marriage are not going to lead to your happiness. They’re just not. Relationships are hard. Honestly, sometimes I wonder if they’re worth it! But then, I’m quickly reminded that they are because they mean you change and grow — ideally with someone that you love so deeply. As Gary Thomas shares in his pivotal book Sacred Marriage, relationships are about your holiness, not just your happiness. Relationships can be so much fun (see 3 above), but even more than that, they’re the best change agents I know. When I’m in my own safe little bubble, it’s all too easy to get comfortable with my little sins. But when I’m in relationship with people — romantic or otherwise — they act like a mirror, reflecting both the rough and the beautiful parts of me. And I never want to lose that.
6. Don’t date someone you wouldn’t want to be friends with in another context. Just because they look great on paper or the match seems to “make sense,” it doesn’t mean it will. If you don’t have fun together, if you don’t make each other laugh, if talking is still like pulling teeth months into the relationship, it’s probably one to let go.
7. At least once in your life, try going on dates with multiple people at once. (If you’re already married, forget I just said that.) This approach is not for everyone. But if you’re being honest with all your dates and you’re not just trying to “fill the void” — hello my 21-year-old self — going on dates with a few different people at one time can be a great learning experience and a ton of fun. You’re getting to know interesting people, and you’re learning more about yourself — what you bring to a relationship (good and bad) and what you need from the other person. For me, it also helps me get not go too deep too fast (see 2 above).
8. But don’t use dating multiple people as a barrier to intimacy. At some point, you’re going to have to choose one person to continue dating in order to get truly close with them. So, don’t put that decision off for long. When the time comes — and you’ll know when that is because you’ll have that gnawing pit in your stomach — you’re going to have to put your big-girl or big-boy pants on and do the hard thing of ending the other relationship(s) for the sake of going deeper with one.
9. And when you do end things, I highly recommend doing so in a public place that is not a restaurant. Pick a wine bar or a park — some place that’s neutral ground and provides the safety of other people around you, but also a place where a waiter or waitress is not going to be constantly checking up on you and your soon-to-be non-date. Observing tears that aren’t yours to witness is just plain uncomfortable.
10. Own those tears. Whether they’re your own or ones you’ve caused — own them. Apologize, forgive, show grace. And, as my wise sister would say, realize that tears are a lot like a sneeze. You just have to let them out or you’ll be severely uncomfortable.
11. Talk about your exes like they’re your best friend’s future husband or wife.Remember that even though they’re not the one for you, they’re the one for someone else. So, it’s probably best not to throw them under the bus all the time.
12. Give so much grace. To yourself. To your date. To your former dates. As one of my friends recently said, we’re all just messy broken people trying to put the pieces back together. And in the end, we really need each other on the journey back home. So, stop judging yourself for your imperfections and stop looking at your dates through a giant lens of scrutiny. (I’m really talking to myself here!) While it can be really tempting to analyze people and relationships in the name of “wisdom,” I’d advocate that we need to give more grace. At least, that’s what I’m trying to remind myself because Lord knows I need to get better at that.
13. Physical closeness is not the enemy. Growing up in a conservative Christian context, I interpreted some people’s teachings and books like I Kissed Dating Goodbye as saying that physical affection would most certainly lead to sex and that sex is the worst possible thing you can do. Actually, maybe that’s what they were saying, but I don’t really see it that way anymore. I 100% agree that sex before marriage is not a good idea — my story is case in point (more on that another time) — but I think we’re approaching it the wrong way. Instead of beingafraid of physical closeness, let’s shift to viewing it with a lens of awe and respect. I adore my married friends who share with me about their sex lives — in appropriate detail, of course — because they’re helping me see that sex is at once awkward and awesome. To quote this article: “In marriage, good sex is even more than just sex. It’s about cultivating the exclusive, deep connection you have together and enjoying the passion and fun that comes with figuring it all out along the way.” I’m looking forward to that someday.
14. However, marriage is not the end all be all. Our culture, and the church especially, are often guilty of elevating marriage as the highest goal of life and treating singles as second-class citizens. The truth is that in the Bible, Paul actually touts singleness as a better place to be. Why? Because there is such freedom in being single! You’re free to be used by God however he calls you, without checking in with a spouse. You’re free to go on adventures. And you’re free to pour into relationships other than just that one. This is not to say that marriage isn’t wonderful (again, see 5 above). It’s simply to say that maybe we’ve gotten too single-minded (pardon the pun) about marriage and need to stop caring quite so much about someone’s “relationship status.”
15. You have to be OK on your own. This is the hardest thing — believing that you are enough. Dating will not cure your loneliness or your boredom. I am reminded of this over and over again. Even when I’m in a relationship with someone or going on dates, I still experience loneliness. Especially in a city this big and in the swirl of social media, it’s easy to feel like everyone else has something better going on. This is not true. Everyone’s relationships are hard. Everyone’s life is a little rough around the edges; it’s just that they’re only showing you select pieces of themselves and their lives. So, get to know yourself through the process of dating and through time on your own. Go for a walk, take a class, do something that inspires you. And hey, you may just meet someone wonderful along the way.