Updates: “May-December” Responds

It’s time again for “Dear Wendy Updates,” a feature where people I’ve given advice to in the past let us know whether they followed the advice and how they’re doing now. Today, we hear from “May-December” who was dating a man 22 years her senior and wondered if he was too old for her, especially since she hoped to have children and worried that he’d either not want them with her (he already has grown kids) or wouldn’t be alive long enough to help her care for them. My response to her sparked a heated discussion and the column turned out to be one of the most popular posts of the year. Keep reading to see how the LW is doing today.

I appreciate you running my letter! It was insightful to read your response–and the commenters’. I did not expect you to take the “biological clock” tinge, but it did get me to thinking.

I am happy to report that my relationship with Boyfriend has only gotten stronger since I first wrote to you. We are currently looking for a house together, and we have been discussing marriage for a few months. My relationship with his daughters is developing as well as it can from 1,000 miles away; we’ve visited twice and they’ve visited here once. His kids are super nice and welcoming and open-minded and, above all, sincere. Their relationship with their dad is very good, and I really believe they would tell him if they had a problem with him dating someone who is closer to their age than his, but all they have expressed is happiness that he is happy. The way they “turned out” makes me feel even better about the prospect of having a child with Boyfriend.

In the many discussions Boyfriend and I have had about our future, we decided very clearly that we will try for kid(s) after we get married. He is now fully on the bandwagon. Our timeline is more “rushed” than it would be if he were younger, but I don’t mind that. I never wanted to be an “old” parent, anyway. I was talking to my best friend, who is the same age as me, a few weeks ago, and she told me that she still definitely wants to have kids, but definitely NOT within the next five years. Her revelation really blew my mind, as I am now so looking forward to trying in a year or so! I don’t feel that his age is pushing us into marriage or children, it just makes us both more honest and open about our feelings and goals and wants for the future. Our discussions just start a little earlier than most peoples’.

So, I am now 29 and he is now 51, and our relationship continues to get stronger. He is such a “young” 51 that most people who meet him casually think he’s about 40. His personality remains very youthful (in a positive way, not an immature one)! I feel happier now than I have in years. Knowing he’s there for me has brought out the best in me in other aspects of my life, as well.

One last thing I want to address — many commenters mentioned finances. This is at the forefront of my mind, as well. There is no doubt that it will be challenging for us at times, but we both feel that we can make it work. He has no visions of retiring and, in fact, has said he would prefer not to. Men in his family who retire, even those who retired young, have all died within the year. Not that it wouldn’t be nice to have a retirement fund “just in case,” but it’s not the reality. Luckily, his attitude and work ethic match that reality! Aside from a decent living standard, I am adamant that we have health and life insurance due to his age, and we do our best to live within our means. I feel confident that we can do it. I am currently in grad school and should be at a much higher income bracket when I graduate. “Should,” of course, is the operative word, but I’m trying to be optimistic rather than pessimistic! I’m in school for a field with much movement and opportunity.

Overall, just wanted to send the update. I was happy and a little surprised to see that my letter made your top most popular posts of 2012!

Thank you so much for your update, and best of luck to you as you make your exciting plans for the future.


If you’re someone I’ve given advice to in the past, I’d love to hear from you, too. Email me at wendy@dearwendy.com with a link to the original post, and let me know whether you followed the advice and how you’re doing now.

You can follow me on Facebook here and sign up for my weekly newsletter here.

If you have a relationship/dating question I can help answer, you can send me your letters at wendy@dearwendy.com.


  1. Hmm. Well, glad the LW is happy. It’s good that they are going to save money for retirement “just in case” because sometimes you don’t choose retirement, it chooses you. It’s not always about somebody deciding they want to garden or go fishing. It’s also about making sure you have money in case someone becomes disabled or otherwise unable to work, or maybe gets laid off at an age that makes it hard to find work again. Also, I know the implication is that retirement caused the men in the boyfriend’s family to die, but you never really know. Seems like a chicken and egg sort of thing. They still easily could have gotten sick while they were working and been forced to retire.

    1. I realized that I kind of sounded obnoxious at the beginning of my comment. I really am happy for the LW, and it sounds like things are really going well!

    2. Sophronisba says:

      And also life insurance. When you get married, both of you should purchase sizable term life insurance policies (while you are both in good health) to provide security for a surviving partner and/or child(ren) in case of the unthinkable. Good luck!

  2. kerrycontrary says:

    I’m glad things are going so well!

  3. Sue Jones says:

    Hey, I’m 51! 51 is NOT old. Though I am thinking about perhaps retiring in 10-15 years and would not want a newborn right now… Best of luck!

    1. Avatar photo Addie Pray says:

      Yea but you’re awesome and you have amazing stories from India. Also, with this comment BOOM all AP in the recent comments!

      1. Avatar photo Addie Pray says:

        Damnit, kerrycontrary ruined my streak.

        Also, Sue Jones, have you told your kids about India? It makes me wonder what stories my parents had that I’ll never know about…

      2. Sue Jones says:

        They will never know the details…. NOR will they know specifics about all the drugs I took during my Grateful Deadhead college days… And to look at me today I look just like any cougar suburban housewife…(though I am not an official cougar since my husband is 3.5 years older than I am). My husband is a more “tell them everything” kind of guy, but his stories pale in comparison to mine and there are some things that kids really do not need to know about!

      3. Avatar photo Addie Pray says:

        You’re an inspiration. Do you wear mom jeans? I’m picturing you in a suburb wearing mom jeans…. with HUGE AMAZING SECRETS HIDDEN UP IN THERE! I love you.

      4. Sue Jones says:

        No, AP, I do NOT wear Mom Jeans!!!!! OMG! I am not THAT kind of suburban mom! I haven’t quite made the leap to skinny jeans, just because that would be perhaps ridiculous, but I am considering getting a pair of “jeggings” to wear with some long tops… On non work days I usually wear yoga pants! (Mom jeans, indeed! Hmmph!)

      5. Avatar photo Addie Pray says:

        No, see, I want you to wear mom jeans because in my head you are like an undercover badass! Mom jeans are just a cover, they’re your clark kent…. and then BAM stories of India come out and people realize you’re superman! my analogies are all off but the point is you need mom jeans! it’s ok, yoga pants are the new mom jeans. and the new black party pants. and the new everything.

      6. Sue Jones says:

        Black yoga pants are the BOMB!!!!! I have no use for Mom Jeans!

  4. lets_be_honest says:

    Glad to hear you are happy LW!

    This was a really interesting letter back then, and the comments were too. My opinion changed quite a bit, which is funny. In skimming, I noticed I wrote this: One of my closest girlfriends was out with me Friday night discussing her relationship with her boyfriend of two years. She’s totally in love with him, he’s a great guy, she’s 30, he’s 37. She’s wanted kids her whole life but he doesn’t want any more (he has a 13 y/o from a previous relationship). Its so sad for me to hear her try and convince herself she would be ok with not having kids because she so clearly wants them.

    She’s still in the same boat. So sad.

    1. lets_be_honest says:

      Oh, I even got snippy with theattack! Sorry ta!

      And then a classic piece of advice from someone else “if he watches Fox News, dump him and move on”

      1. Avatar photo theattack says:

        Apology NOT accepted!

        ……..just kidding! <3

  5. Amazing!!! says:

    Good for you! Although I could never see myself with someone much older, my parents are actually 20 years apart in age and have been married for 34 years! My father had me at 50 and does not regret his choice. I will say that as I’ve gotten older seeing him age (now 80 years old) is getting a little scary, but he’s in pretty good health and didn’t even retire from a somewhat active job until he was 70. So just brush off any negative talk and enjoy your future because it can work and work very well.

  6. LW, I’m glad you seem happy, but I just wanted to throw my two cents in here.

    I’m not judging or anything, but for me, the biggest thing with age differences in relationships is the fact that the two people are usually in completely different places in their lives. This guy already has grown children. You’re just getting your career off the ground and I’m sure he’s thought about retirement. Can you imagine working for thirty years and then suddenly having a kid or two to take care of?

    1. Yeah, I am glad she’s happy, but my issue with age differences is exactly what you said—the “stages of life” thing. It often becomes more of a problem than people anticipate.

    2. camorzilla says:

      Did you actually read the update? They’ve discussed the things that would be issues for you and those things aren’t issues for them.

    3. Avatar photo Addie Pray says:

      Yes, I can see why at 51 her BF wouldn’t be on board, but he’s on board, so…..

      1. lets_be_honest says:

        If I were 51 and a hot young man was boning me, pretty sure I’d give him anything he wanted too! Bah Blam!

    4. ele4phant says:

      Well, he surely can imagine what it will be like, seeing as he has raised children before and knows what he is getting into by agreeing to have more. Also, apparently he doesn’t intend to retire any time soon, maybe never.

      So perhaps they’re not actually in such different places despite the age difference.

  7. The LW is too cavalier about saving for retirement. Even if bf works until he drops, she still actuarily has 26 years of life ahead of her. If they have a kid right away he’s 74 when kiddo graduates college. For most of us, it’s not easy working at age 74. Also, if men in his family die within a year of retirement, even early retirement, then, unfortunately, bf is not a good bet to see 74. Th

    1. Yep. Sounds like she doesn’t really understand the concepts of retirement or aging very well. I’ve honestly never heard someone try to make a logical case for why they shouldn’t save for retirement.

      1. lets_be_honest says:

        Duh Lindsay. Anyone who knows the day they will die has a very logical case for not saving for retirement!

      2. Yeah, it almost sounded like she is thinking that as long as he doesn’t retire young, he won’t die young. Pretty sure that’s not how it works.

      3. Avatar photo Addie Pray says:

        Or maybe the men in his family retired young because they were feeling too tired to work and had pain and whatnot and then BAMMMMM HEART ATTACK. It’s like that old riddle, what came first, the chicken or the heart attack. (I dunno.)

    2. I think way too many people are cavalier about saving for retirement!! I’m obsessed with my 401(k) 🙂

      1. Avatar photo Addie Pray says:

        ugh, i stopped looking at mine years ago. it’s too depressing. or at least it was in 2008, when i last looked at it. maybe i should check it.

      2. That’s good strategy. Check every 5 years. Then you won’t notice how much/little interest you’ve collected, just how much you’ve put into it!

      3. lets_be_honest says:

        You should. I stopped checking for a while too because it just pissed me off. Its gotten better lately though, hopefully ours has too.

      4. I just checked mine, and I’ve made over 11% return so far this year, on average, which I’m happy with.

        I just realized that I had a bunch of $$ sitting in a money market, so I diversified that shit.

        I try not to check it too often though, or else it gives me anxiety.

    3. And? Some people are still kicking ass at age 74. I am 29 and my dad is 73. He chose to retire and has adequate income from social security and pension but he still works on his farm, which is a lot of physical labor. If he needed to go back to work, he could. He’s also a cancer survivor who went into remission 10 years ago and decided that sitting on the couch taking it easy isn’t the life he wants.

      1. lets_be_honest says:

        I’d think it would be pretty unlikely though that it would be easy for him to find someone to hire him at 73 though. Just something for the LW to keep in mind.

      2. Liquid Luck says:

        Plus, social security and pensions are less available now, and will most likely continue declining from here. Even if he’s capable of working AND can find a job, there’s no guarantee it will be at the pay level he’s used to or be enough to afford whatever bills they incur.

      3. That’s true. But it’s not necessarily safe for everyone to bank on that happening to them.

  8. stilgar666 says:

    Sure, everybody is happy that the LW is happy…this still sounds like a naive and trashy situation.

    1. Avatar photo Addie Pray says:

      Why naive?

      Ha, I’m in one of my moods.

    2. ele4phant says:

      Um, I couldn’t imagine dating someone closer to my father’s age then my own, and the lack of concern about retirement/saving would be worrisome to me, but trashy? How so? That seems a bit unwarranted.

      1. stilgar666 says:

        He’s 22 years older, sounds like a real manchild. There is a reason he isn’t with somebody closer to his age.

  9. Avatar photo Addie Pray says:

    If you’re happy I’m happy, LW! Hey, I’m just curious, can you tell us the difference between 51 year old balls and, like 30-something year old balls? Sorry if that’s too nosy (Ha, I can’t think of anything nosier.) Like, do they dangle down really far? Are they squishier? Weird colored? Oh come on everyone is dying to know.

    1. kerrycontrary says:

      I am def dying to know. I assume they are like boobs and gravity takes its toll.

      1. Avatar photo Addie Pray says:

        Yea, or maybe the balls start twisting into weird shapes, like hook or something.

        Also, does gravity take its toll on the penis?

      2. lets_be_honest says:

        Did you ever notice that balls constantly move? I wish I could drop acid or something like that just to watch the balls move. Its fascinating.

      3. If my hand is down there, I always start absentmindedly playing with them. They’re so weird! (Also, no guy likes his balls absentmindedly played with. NO. GUY. Especially if you have some sort of distant expression on your face as you’re doing it, haha)

      4. lets_be_honest says:

        Ew you touch your boyfriend’s balls?! Gross Fab 🙂

      5. Who DOESN’T touch their boyfriend’s balls?! Amirite?!

        Yesterday my “boyfriend” (or whatever he is) totally called me out for inspecting a freckle he has down there. Can’t I look!? If it’s just hanging out there, I’m gonna look. Just sayin.

      6. Avatar photo mrmidtwenties says:

        I would accept someone absent mindedly playing with my balls at this point.

      7. Trixy minx says:

        Dear Wendy the pick up site? Lol

      8. It’s amazing to watch. My husband thinks I’m a freak haha

      9. I avoid balls like the plague. I know you’re not supposed to do that, but I do. I am not a fan.

      10. Avatar photo Addie Pray says:

        I love balls. Know how Middle Eastern mean sit there and play with those beads? I don’t know what they’re called but my dad had some – these beads on a string and they just roll them aroudn in their hands. It was always annoy me when my dad did that because they’d clink and clank and it was just really distracting – like if I were doing my homework at the table or someth9ing. ANYHOO, i like to play with balls like that, just roll them around in my hand, while i’m watching TV. kind of soothing, for both parties.

      11. WORRY BEADS! My mom bought me some – they are a greek thing too (I’m not greek)

    2. There’s no difference. Other than the usual differences between different men’s bodies. No difference because of the age. Oh, the hair might be gray. Hope that helps?

      1. Avatar photo Addie Pray says:

        No we need more details.

      2. Haha Addie Pray, you were in a mood today, weren’t you! Well, that 51-year-old pair was the last pair I saw, and it was quite nice. Yes, exactly 51– younger than me– my toy boy I guess? 🙂 Well, that got me thinking about that stuff, which I had removed from my brain after that ended. And it made me wonder how he has been doing. Then I decided to join a dating site today. You young folks are wearing me out.

    3. Avatar photo Addie Pray says:

      Also, and kind of along the same lines, LW, I think you should tell us all the funny/weird observations you’ve made since dating a 51 year old. Like what the balls look like. That’s one thing. But what else? Like, any generational things? I can’t even think of anything. But I remember when I was in my mid 20s I dated a 42 year old for a hot second and was really taken aback when at brunch before he ripped into his steaks and eggs he popped some cholesterol medicine. First time any friend of mine had a cholesterol issue. Also his gray chest hair was so WEIRD! Now of course that wouldn’t be such a big deal.

    4. No dramatic difference. They hang a little lower. Aren’t really any more wrinkled. Usually all the equipment works just fine on a superficial basis at 51. However, 51-year old balls pump out sperm with more mutations and less overall viability and numbers than 21-year old balls do, so rates of birth defects and miscarriages increase. Also, 51-year old balls aren’t quite as up for twice or three times a night as 21-year old balls are. They also pump out less testosterone, so desire can start to diminish in not a small proportion of men. That can also make those men smell less sexy.

      1. Liquid Luck says:

        This is a good point. Most people forget that just because men are capable of creating children longer than women, it doesn’t mean that age isn’t a factor for them. Women are given a hard time about being “older” mothers because of the higher risks for the baby, but men are rarely treated the same way despite the similar problems. It’s a pretty crappy double standard.

    5. landygirl says:

      Ummmmm eeeeeeeeeeeeeeeeeeeeeeeeeeewwwwwwwwwwwwwwwwwwwwwwwwwwwwwww.

    6. I laughed out loud at your question, Addie! Coming from a 28-year old who has seen a fair range of the articles in question, and is currently dating a 47-year-old …

      They’re the same! I can’t see any difference between a 47-year-old pair and a 22-year-old pair. The things that are really noticeable to me are the grey chest hairs and the loss of elasticity in his arm and back skin.

      1. Avatar photo Addie Pray says:

        Oh oh, also old men get really thick knuckles and fingers. Have you noticed that? They’re like fat sidewalk chalk. But hairy.

    7. OMG, AP! You crack me up! I always love to read your comments. I think I have an Internet girl crush on you 😉

      1. Avatar photo Addie Pray says:

        MissD, my new favorite commenter! Where have you been all my life?!

  10. And once again we learn that Wendy can’t subtract to save her life.

    1. Avatar photo Addie Pray says:

      Man, I kept doing the math in my head and almost called you an old idiot b/c clearly 51-29 is 32!

      Ahem, 22. Still.

    2. Trixy minx says:

      Neither can a lot of people. Don’t have to be rude about it.

  11. This is the most grounded LW to appear on this website in weeks….good for you! Congratulations and best of luck in the future!

  12. Yay for a good update! I like when readers take a long time to update. I think some of the people who update quickly tend to get a little defensive with some of the comments, instead of letting it all soak in and looking at the bigger picture, which can be understandable.

  13. “Men in his family who retire, even those who retired young, have all died within the year.”

    Well that’s ominous.

    1. If by “ominous” you mean “spectacularly poor reasoning born out of a desperate attempt to rationalize an unwise decision,” then yes, it’s quite ominous.

      1. Ha, yep, when I read that, I thought, “Well that’s a convenient excuse.”

      2. That’s what I meant! Haha.

        I just thought the line sounded pretty creepy. “If he retires he will die a fortnight hence. Such is the curse of the House December.”

        I don’t know. I read everything like it’s a passage from Game of Thrones. 😉

  14. Bittergaymark says:

    Ugh. Another man dropping a litter of kids with each and every relationship. My pet peeve. So narcissistic AND fucked up… Just gross to me. Fucking off-to-hurl-by-the-side-of-the-road gross…

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