This is generic advice, aimed at no one in particular (except a few older men I work with who won’t ever have the opportunity to read it). I’ve been mostly single my whole dating career – a few three to four month interludes throughout the years – and I’ve only recently come to terms with it. Throughout those years, though, some things are constant.

1. Always (always, always, always) think before you open your mouth. This is especially true when conversing with a single woman nearing 30. So, if you find yourself in a situation where you’re not quite sure if what you’re about to say is going to offend me, take a few seconds to consider just how awful your own foot might taste when it’s stuffed into your mouth.

2. Don’t worry that there’s something wrong with me because I’m approaching 30 and haven’t yet had a stable, long-term relationship. It’s like Deborah Kerr said – “Personally, I think if a woman hasn’t met the right man by the time she’s 24, she may be lucky.”

3. Stop telling Cat Lady jokes. Seriously, just stop.

4. Just because I’m happy without a romantic relationship in my life, doesn’t mean I’m prepared to walk into a room full of couples by myself. Bravery is one thing, but stupidity is a whole other. Cosmo Magazine would never tell you, but that’s why gazelles travel in groups – because it makes it harder for the lions to pick one out for dinner.

5. 99.9% of the people who are in loving, wonderful relationships are the EXCEPTION. I think it’s wonderful that you met your husband or wife by chance while choosing melons at the local market, but stop telling me that I need to shop for melons on a daily basis so I can meet the love of my life. I don’t even like melons.

6. Please stop telling me that it will happen when I’m no longer looking. The reasoning here is twofold: first, because I’ve stopped looking and it’s still not happening and second, because if this statement applies to dating then shouldn’t it apply to most other things? For instance, if I’m constantly looking for a bus and it doesn’t appear, then the minute I stop looking for a bus one will show up…and most likely run me over. This seems unpleasant.

7. Hollywood: STOP MAKING ROMANTIC COMEDIES. They’re not funny, they cause damage to one’s self-esteem, and they create unachievable goals in a world already filled to the brim with broken hearts. See here.

8. Not everyone gets a “happy” ending. Some people get the ending that makes them happy.

9. Do not (I repeat: DO NOT) suggest online dating to me when I complain about how difficult it is to meet men in this day and age. I won’t even say anything. I’ll just throw something at you (most likely something soft…maybe). Just let me bitch and moan and then tell me to suck it up and eat a cupcake.

10. Don’t worry so much. Life happens at a pace it sets for itself. You’ll be the first to know when I’m head-over-heels in love. Until then, let me be. I have a wonderful group of friends and for now, they keep me sane.

The 6 month sabbatical was supposed to end this month. I don’t think it will, at least not officially. I’m not saying that if some approximation of my better half pops up in front of me and asks me to dinner I’m going to say no. I’m just saying I need some more time to figure it out…whatever the hell “it” is.

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Putting aside her commitment to the National Ninja Association, this young, bright and talented author has finally come out of hiding. She currently exhausts her brain capacity working for government, but spends many afternoons dreaming up new ideas for her incredibly blasphemous novel, The Absolutely, Positively, True Adventures of a Religious Prophet, while keeping her typing fingers limber. She can be reached here on the comment board or over at her blog, The Unbelievable Adventures of Claire Elizabeth Rogers.

32 responses to “10 Pieces of Advice on Conversing with a Single Woman Nearing 30 from a Single Woman Nearing 30”

  1. Matt says:

    I was single when I turned 30, after having been in a relationship for most of my twenties. That was a motherfucker, let me tell you.

    Whenever people tell me to try online dating, I say sure – as long as they’re paying the site’s subscription fees. No one’s taken me up on that so far.

    • Richard Cox says:

      I would think a guy freshly single at 30 after being in a relationship for all of his 20s would be ecstatic. I mean, unless you were mourning the relationship. Then I guess it would suck.

    • Meg says:

      Oh god, the online dating sites are ridiculously expensive. It’s unbelievable how they want you to sign away your soul and pay them half your life’s worth just to have them match you with people who are scary.

      In some ways I think I’m very lucky to have never experienced the heartbreak of a long term relationship dying off. In others I feel like it’s an experience I would like to have someday. Not right now, though – there are other things I’d like to experience that leave less of a permanent mark.

      Thanks for reading and commenting!

    • Gloria says:

      I LOVE online dating. It’s a circus.

      Okay, I don’t love it. But I do keep going back to it. And I have actually met some really nice people.

      Also, OK Cupid is free. (Though, Meghan, I swear to god I am not telling you you “should” go on there. To each her own, sister. I get it.)

  2. Mo says:

    Ouch. I’m probably guilty of saying at least some of these things to people. (If ever to you, thanks for not throwing things 😉 ) And I know I’ve been on the receiving end of some of them.

    One thing I’ve noticed in other people, and myself, is that when a friend talks about being single, there’s an automatic urge to encourage them (the ‘stop looking’ comment) or attempt to boost their self esteem (‘but you’re so pretty!’ or some such… even when it’s true 😉 ). That kind of knee-jerk sympathy needs to be trained out.

    Anyway, your point is a great one and your priorities are extremely reasonable. Yay!

    • Meg says:

      Aw, Mo. 🙂 I only throw soft things at my friends because I know you guys are just trying to be supportive and helpful and loving.

      Thank you for reading and commenting!!! And for thinking my point is a great one and my priorities are reasonable – that’s exceptionally supportive. 😉

  3. Richard Cox says:

    Hahaha. I like 7 and 10 in particular. Romantic comedies suck. Well, except for a couple that don’t. But the exception proves the rule.

    • Meg says:

      I think that number 10 is the best piece of advice I can give people (friends, family, acquaintances, etc.) because there’s so much else in the world to be concerned with that doesn’t involve the state of my love life. In fact, pretty much everything else in the world doesn’t concern my love life. 🙂

      • Richard Cox says:

        To add to this idea, perhaps number 6 could be reevaluated. Because if one has really stopped looking, then noting that “it” hasn’t happened wouldn’t be relevant, right? Unless really one secretly continues to look? 😉

  4. J.E. Fishman says:

    The companion piece to this one ought to be What Not to Say to Childless Couples in Their Thirties. We waited a long time before having a kid, which subjected us to endless questions about when were we going to have children, do we want children, have we thought about children… After being flabbergasted by the gall behind these questions for a number of years, I finally settled on the perfect response: “When we decide, you’ll be the first to know.” It’s more polite than, “Mind your own fucking business.” And, usually, what asses they’ve been doesn’t settle on them until they get home.

    • Meg says:

      I’ll bet for a lot of them, it doesn’t ever actually occur to them just how big of asses they’ve been. I have friends going through the same issue at the moment and I’d like to yell at their families for them. Nosiness does not equate to helpfulness and supportiveness. It’s just as detrimental as caring sometimes.

      Thanks for commenting!

  5. Anne says:

    Meg! Please, Please, P-L-E-A-S-E keep an eye out for those buses! And I’m not using the bus as a metaphor. 😛

  6. Greg Olear says:

    Thirty isn’t even the new twenty. Thirty’s, like, the new sixteen.

    You only just had your Saturn Return. You’re not supposed to pair off longterm before your Saturn Return. Unless you’re a star in one of those Hollywood rom-coms you cite. Hollywood starlets have a long history of enduring marital happiness.

    If someone paired off gives you crap about not being paired off, just say, “I don’t want to settle, like you did.” That’ll shut ’em up.

  7. Jillian says:

    All I have to say is “AMEN SISTA!!!!!”

  8. I’ve written two essays on here about the issues that come with moving from almost-married to being single. And, I’m less than a year from 30, though I’m male. So, I hear you.

    Especially on “when you stop looking…”

    How about if I just don’t care? If my perfect woman is out there, so be it. Am I going to FIND her? Who knows? Does it matter? No. More people should be okay with being single and the great tragedy is that many are not…

    My mom keeps asking me if I’ve found a girlfriend…yet. I tell her to ask my sister when she’s providing more grandkids.

  9. Pshaw…30 is nothing. No worries. (Funny stuff).

  10. Meg says:

    I love that the bulk of commenters this time around were men! Yay for pulling in the male readership. 🙂

    Justin – Yeah, the “when you stop looking” line gets dropped on me at least once a week by some of the people I work with. Thankfully, my parents let me do my own thing. Other family members (of the extended variety) still ask questions, but I usually say something about ‘hot hate sex’ and they leave me alone. My mom knows I’m terrified of children, so she doesn’t ask anymore. 😀

    Richard – I’ll hopefully remember that when August rolls around next year and I’m in the fetal position under the covers of my bed, refusing to come out. 🙂 Unless Luke Wilson is in there with me, in which case I’m refusing for all different reasons!

    • Richard says:

      Well, as a way past 30 man, I for sure can nod my head and say, “Yep, that would be stupid.” OR “Yep, I’ve done that. I’m an idiot.”

      Curious – have you tried dating another writer or is that too much? As a writer, I always liked dating fellow creatives, but got married before I really dated another writer. I could see that being really cool, or really painful and mean. Certainly wouldn’t be boring, right?

      • Meg says:

        I haven’t yet tried dating another writer. To be fair, I haven’t actually met that many male writers down here….so either I need to get out more, or I need to find the male writers’ hidden lair. Funny, single writers of the Baltimore, Maryland area – come out, come out, wherever you are… 🙂

  11. Simon Smithson says:

    “8. Not everyone gets a “happy” ending.”

    Lady, you are going to the wrong massage parlors.

    • Meg says:

      I somehow knew you’d pick up on that…

    • Gloria says:

      Okay, not to be completely dough-headed. But can women also get the “happy ending” at massage parlors? Is that a thing? Really? REALLY??

      • Richard Cox says:

        More importantly, can men sign up to provide this excellent service?

        • Gloria says:

          Only if there’s training available first. Otherwise, it’ll once again and always just be an exercise in futility.

        • Zara Potts says:

          Funnily enough – there is a brothel opening up in Auckland catering only for women. I think they have just begun recruiting. I’m curious to see how it does..

        • Reminds me of Jack Donaghy’s “Porn for Women” network on 30 Rock.

          “You’re a great woman. You deserve a great man. For just $24.95 an hour.”

        • Zara Potts says:

          That’s a great tag line! It’s actually a friend of mine who’s opening this place – It’s getting a huge amount of press because it’s just so unknown – whether women will actually pay for sex.
          The critics say that it won’t work, but she’s pretty convinced that there’s a market. It will be interesting to see if she is right.

  12. Add to this growing list of self-help titles: “What Not to Say to The Parents of an Only Child”….when are you having another one? Aren’t you worried she’ll be eccentric? Does she have imaginary friends? Was this an intentional decision? Have you ever read The Bad Seed? One of my best friends growing up was a only child and she…(choose: is in jail, is insane, got pregnant at 13, is a performance artist, frequently sniffs her wrist, etc.)

    • Gloria says:

      Oh, how about: “What Not To Ask a Parent of Twins” – Which one is the smart one? Are they twins? They’re double trouble, aren’t they? You must feel so lucky; I’ve always wanted twins! [pointing] Which one is that again (as your child stands there, able to give his own name to a person he’s met six times)? Do they have their own language?

  13. Amanda says:


    Yes yes yes and yes.

    As a single women nearing 40 (well, I’m 2.5 years away, but that’s pretty fucking close-feeling these days), I’m not sure if it’s good or bad that all of the points in your post continue to be relevant, identifiable, daily parts of my life.


  14. Carolyn says:

    I am thirty and single. Would I like to meet that “special someone”? Sure, but I am not going to “pretend” either. What is the divorce rate? That’s right 50%. Look around, how many couples do you see where one of the participants looks like they are in a coma. That coma look isn’t an isolated event, it’s usually every time you see that couple. If people where more honest, single would be normal.

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