single advice

You found love! Mazel Tov!

I loved being your wing-woman. I made myself scarce when you started vibing with that cute guy during our girls-night-out, played third wheel when you began dating, helped him pick out your ideal engagement ring, bought you drinks at your bachelorette party, and danced at your wedding.

Now that you’re married, I love still being friends, but sometimes you say things about relationships that aren’t helpful for me as a single woman. So, as I’m still navigating the world of dating and heartbreak, here are some things that aren’t the most helpful for me to hear:

“It’ll happen when you least expect it.”

I understand that people are trying to say “you can’t control when you’ll meet someone,” or “there’s beauty in meeting someone in a serendipitous way,” or “try not to exude desperation, it turns people off.” However, there’s many reasons why this statement is so unhelpful:

– How can you “least expect” something? The harder you try to not think about it, the more you expect it. People are doing mental gymnastics trying to convince themselves they don’t want something that they actually do.

– In every other arena of our lives, we work towards our dreams. Would you ever advise someone “you’ll find thousands of dollars in savings when you least expect it” or “you’ll graduate college when you least expect it?” No. We should map out a path to our dreams, appreciating it can take hard work to get there.

– Most singles likely had a season in their life when they had no interest in dating someone…. And didn’t. If this statement was actually true, wouldn’t those people all have met “their person” during those seasons when they actively were choosing to be single?

– This makes it seem like it’s shameful to desire love. For every person who finds love when they least expect it, there’s another who found love by searching high and low actively expecting to find their beloved.

What’s more helpful to say: “It felt like it took forever to find ‘my person,’ and sometimes singleness really hurt. But one day, just a normal day, everything changed. Literally any day is a day your life could change forever.”

single advice 2

“You don’t really want to get married, it’s so hard.”

It’s true I don’t know how hard your marriage is… Or isn’t. Every couple deals with their own set of issues. Some issues are really hard, harder than others.

As your friend, if you’re dealing with some difficult challenges in your marriage, I’d love to be a source of encouragement. Please, give me a call.

However, just as I desire a beautiful relationship for you, I also desire it for myself. I’ve been waiting a really long time to find it. So please don’t minimize my desires, just because marriage is hard.

What’s more helpful to say: “Marriage is really hard.” That’s it. Don’t tell me what I want.

“I remember dating in college, so I totally know how you feel.”

Dating at 22 is very different than dating at 32 or 42. When you’re in college you may feel like you have all the time in the world. Marrying young is very different than marrying older, as well. If you married young, let’s just acknowledge that our 20s were very different.

However, when you’ve had 10 or 20 years of relationships not working out, it can feel like each failed relationship is a compounding pain. Dating in college feels like you’re just one party away from meeting your next fling. It’s loaded with hormones and butterflies in your stomach.

Dating at an older age is less hormonal and more mature. You’re facing questions like “could I be a step-parent?” or “should we hurry into this wedding, we’re afraid time’s running out to have kids?”

What’s more helpful to say: “How is dating now different than in college?”

single advice 4

“Are you guys planning on getting married soon?”

Sometimes being single means you’re dating, but not married. After a certain age, it makes sense that people ask if you and your partner are heading towards matrimony, but it’s better to let your friend bring up the topic.

Sometimes couples are going through a rocky patch and this question only makes that conflict harder. Or maybe they just don’t ever want to get married. Or sometimes they just don’t know yet.

This may seem like an exciting question to ask, but it can become a source of pressure for a couple who may just need more time to figure this answer out.

What’s more helpful to say: “How are things going in your relationship?” That’s it, I’ll volunteer the rest.

“I got married before Tinder. It seems fun. Can I do some swiping?”

Nope. That’s my app. Back away.

Granted, some people may be down to let you play with their dating apps, but it’s rude to ask. Would I ever say “registering for wedding gifts seems so fun! Can I borrow that laser gun and register for your gifts at Target?”

If I volunteer to let you swipe left, have at it! But these are real people, not a game, so probably better to borrow my phone to play Pokemon Go.

What’s more helpful to say: “I can’t believe how much dating has changed in recent years. Do you think dating apps make it better or worse?”

The bonds of friendship are strong enough to last through all the seasons of our love life, because you can uniquely offer me support in a way that no relationship can. I need you and love you, so let’s ride-or-die for years to come.

What do you wish more people would be sensitive to when talking about relationships?

Images via Cacá Santoro



  1. I am from Europe and I love this magazine as it is so thoughtful. Having listened to the arguments in this article I have to say though that there is nothing to defend nor should it be something to be ‘wounded’ about. Being single is not an illness nor something which is wrong. It is a fact and something if you really look at is – gives you enormes freedom… I remember how much I loved to sleep in and on a late Saturday take an even later breakfast at my favourite cafe…. reading… sitting…talking… I felt always very comfortable during my single years. Perhaps that is why nobody asked much. I realised that I had freedoms my coupled friends did not have! If I wanted to see an exhibition or leave for a workshop at a whim I could do it whilst a lot of my friends said – ohhh I think he as plans, ohhh I better ask first… There is something to be celebrated when one is on one’s own. It is not always easy – but then it is not always easy to be in a relationship. Each time has certain advantages and it is important to take them. A lot has to do with becoming at one with ones choices – regardless of society. Who is society anyway? As more as one is comfortable with oneself – you will notice less questions will be asked…. Incessant questions most of the time come seemingly from the outside when one still asks them on the inside.

  2. I really like what she says about number 1 leading to feelings of shame for what we desire in our lives. I have experienced some of this myself, though not necessarily brought about by the first comment, alone. It makes me feel like my desire to find a loving, long-term, committed relationship is silly or desperate.
    I also didn’t see this article as saying that single people are more sad or less content, or that we don’t want to hear these comments ever as if we can’t handle them. I think the author was simply seeking to bring some attention to comments that become tiresome when we hear them so frequently or they are said with little thought to how they might make someone feel. I agree that it’s important to have open conversations about the highs and lows of both being single and being married or in a committed relationship. There are things to learn from both sides of the coin.

  3. Lovely advice! I like that this focuses on being gentle and kind, rather than “don’t ever say this to anyone or we think you’re a total monster”. 😉 Many of us haven’t been single for a long time, and may not remember how easy it is to come off as dismissive or insensitive. We often don’t mean to be cruel, but it is good to remind people every so often that even with the best of intentions, we can really ruin someone’s day.

    Well done!

  4. Thank you for this article! Though I’m no longer a single lady, I can absolutely relate to number 1 during my single years. The amount of times I heard the statement “it’ll happen when you least expect it” drove me mad! I never couldn’t expect it, and it made me feel like I should be ashamed to be single in the times I was completely comfortable with it and desired to be. Thanks for offering guidance on how to better support and relate when your pal is single.

  5. Thank you for this article! Though I’m no longer a single lady, I can absolutely relate to number 1 during my single years. The amount of times I heard the statement “it’ll happen when you least expect” it drove me mad! I never couldn’t expect it, and it made me feel like I should be ashamed to be single in the times I was completely comfortable with it and desired to be. Thanks for offering guidance on how to better support and relate when your palm is single.

  6. Hmmm….I don’t think I can agree with the first one. I have QUITE a few friends as well as myself that, once they stopped looking to get married, found that person. While it might seem that the best approach is to “hunt down” a spouse it doesn’t always work that way for all people. And married people should be able to be honest about that stuff without their single friends being annoyed.

    1. I feel like as a piece of advice “stop looking then you’ll find it” — it’s hard to do and hard to believe as a single person. My own mom met my dad at 29 after she “gave up on all men and was done.” For myself ~ it would helpful to know what one did during the interim (did you work on yourself ? Find a hobby? What did you do besides dating??) versus the first statement.

      1. I think context is everything. I like that this article emphasized asking questions other than throwing generic advice at someone. Only that person knows what they are going through so asking questions is essential and shows respect. However, objectively it can be easier to see patterns (especially harmful ones). I have a close person in my life that is literally unable to be single (on marriage #4 before the age of 30) and I would love to help her see that though loving herself she will find deeper joy. On the other hand, I have a close person that dates a lot and although they want a bf, holds everyone at a distance. I’ve decided that the best thing I can do is listen, ask questions and say nothing unless specifically asked. Tell them what I admire about them and maybe recommend a book that I’ve read and think could help them with a new perspective. The fact is they are wonderful, beautiful people who are on their own journey and I accept them just the way they are.

  7. In my world, I am the odd one out of being a single woman surrounded by married friends. I swear my friends are intelligent caring humans but the multiple times I have been asked why or how I am single still is as mindless as it gets. To the married- seek to understand, love and actively engage with your single people. In other words be a friend, most likely your single friends have read a few marriage books and give a decent perspective of the respect and joy, they hope to have when they are in a relationship. But for now be present.

  8. I think this article assumes that single people are living sadder, harder lives. It also suggests that non-single people shouldn’t bring up topics or questions that might be difficult to face and to think about but actually really important conversations to have with people close to you. And sometimes it’s our friends’ job to ask the tough questions. Lastly, there’s so much sensitivity that this writer clearly expects and feels in the world. It’s bad if your friend asks to see Tinder? What’s happening here? I have been on both sides of this and see little merit in the suggestions in this article. And for what it’s worth, a whole lot of judgment, as a woman who once found her “person” but walked away from it to return to a much happier life as a single woman. I’d really like to see more articles from that perspective in this magazine.

    1. I agree with your point of the assuming your life is sadder / harder / worse off as a single person. In reality- it could be viewed as “easier” (less $ than with a partner / schedule freedom) but also lonely. I would love to hear from married couples on how they feel lonely or how they feel similar to when they were single while still in a marriage.

      1. Yes agreed! It seems like our culture just assumes it’s hard to be single and everyone is just looking for the “one” so they can get married and be happy. But I think there are equal parts positive and negative things about both, just like anything else in life. And that’s the kind of article I want to see from Darling.

  9. I have been guilty of doing this to single friends, even though it irked me to no end to hear these things before I was married myself. Thanks for the reminder to choose our words more carefully!

    What’s funny is that this article could easily also apply to what people with kids shouldn’t say to those who desire children but are childless. It’s all the same things, haha! 🙂

    1. YES! My husband and I don’t have kids (and don’t want to), and it’s tough to constantly defend that choice. People can be incredibly dismissive when I say I have no plans to have children. I’ve even heard the “It’ll happen when you least expect it” argument – like hell it will, grandma. That’s what birth control is for, duh!

      I do find that I am more sensitive to my single friends because of this. I know the stinging frustration of people telling me my decisions are invalid or wrong because they don’t align with theirs – and how even one well-meant comment can ruin a person’s day.

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