#192: Should I apologize for being a NiceGuy(tm) in the past?

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Oh Captain! My Captain!

I have what I hope is a quick question.

Background: Back in high-school, I was (and still am, to an extent), an incredibly awkward dude. The more I learn on the internet, the more I realize that I was a Nice Guy™. I wasn’t an egregious Nice Guy™, but it was still there. I also followed the GSFs (not so much #4; even I realized that some circles just won’t get along), even though I didn’t know what they were.

As a result of all this, I was very much a Nice Guy™ to this girl I liked. She was kind of nerdy, and for some odd reason, hung around with me. Unfortunately, for various reasons, I kind of avoided asking her out in a real way, and did it in that passive-aggressive way that avoids any real rejection. We grew apart for various unrelated reasons, and haven’t talked in years. The thing is, looking back on my past, I realize I probably made things quite uncomfortable for her.

The question is, should I send her an e-mail detailing these things and apologize, or should I just let sleeping dogs lie and know that I’ll do my best to avoid being a Nice Guy™ in the future?

A Slightly More Self-Aware Nerd

Please, I beg you, let the dogs sleep.

Look at it this way:  “Hey, remember when I was incredibly passive-aggressive and weird because I really wanted your approval and it made you totally uncomfortable? I’ve figured out that was wrong and am trying to stop doing that. So….can I have your approval now?

Do you want to be that guy?

You’ve had the moment of realization. You’ve had the resulting feelings of shame and embarrassment. This has fortunately resulted in greater self-awareness for you. Your answer is “stop doing the thing you were doing that you feel embarrassed about now,” not “seek this girl out and make her acknowledge your personal growth,” especially since she’s not currently in your life.

Let me give you two steps to being a little bit cooler than you are right now.

1) This may sound weird coming from a lady who named herself Captain Awkward and made a website, but stop describing yourself as “incredibly awkward dude.” That tends to become a self-fulfilling identity thing where it becomes either an excuse or a passive-aggressive way to get people to try to take care of your feelings or cut you slack. Self-deprecation is best in very, very small doses.

2) Fact: A lot of the emotional work we do on ourselves to become functional grownups goes unheralded, and once you’re out of school you don’t get the constant carrot/stick of grades to let you know you’re doing ok. You just have to give approval to yourself when you do well, like “I am more awesome now! Good talk, me.”  Now I? Since we’re here, I will totally congratulate you for leveling up. Good job! But don’t expect people in your day-to-day life to do it for you.

Let the self-awareness be its own reward. Don’t ask for the cookie.

48 thoughts on “#192: Should I apologize for being a NiceGuy(tm) in the past?

  1. Also: It’s possible that the girl didn’t know about your intentions, that she never caught on and thought you just liked her as a friend.

    If that’s the case, she’ll be really weirded out to hear “I was secretly lusting for you the whole time and that’s the reason I was nice to you.” It’ll creep her out and possibly make her question how likeable she is as a friend and whether her current friendships are real.

    If she’s managed to stay under the happy illusion that you just liked being her friend, let her keep that illusion.

  2. LW, as a former Nice Guy myself, I too have felt the urge to make amends with friends (mostly ladies) who I know I treated kind of crap or who’s lives I made sort of worse by inflicting my hang ups on them, whether they realized it or not. But that wasn’t the “new me”, it was very much the “old me”, wanting emotional validation for my self-proclaimed “virtuous” nature.

    We “former” Nice Guys need to understand that those patterns, behaviors and urges that made us like that are still in there, in our (or forming the core of) our jerkbrains, and we need to look inward to ensure that we’re treating the people we meet and (especially) love with respect.

    Let me join CA in congratulating you on what has no doubt been a difficult bit of soul searching, but it’s not an accomplishment, it’s just the first step. Good luck to you!

  3. LW, I will tell you something.

    I used to be a Nice Girl™. I pined after my high school BFF, but only in the background, and he usually had girlfriends, but hey maybe his serial monogamy would turn my way, even though I never ever voiced my feelings, but maybe he would still Notice Me if I was a good enough friend.

    Well, he noticed alright. ‘Twas not reciprocated and I had to move on and past. We’re still good friends and I am, in fact, also friends with his wife. Part of this hinges on the fact that I don’t harp on my old crush. It’s in the past, it’s done, and I trust none of the parties involved think of that when they think of me.

    I want to encourage you to leave it alone too, LW. You’ve learned from your mistakes and that’s wonderful. Let it be your pass to leave your old embarrassment behind (and I get the sense that part of this is that urge to fix the source of an old embarrassment in the wake of your Epiphany) and keep the lesson as your souvenir instead. Dredging things up again will only start the embarrassment cycle anew; may as well absolve yourself of that bit of awkward.

  4. I think there is one situation when going back to apologize helps and it happened in my case. I dated a 21 year old when I was 17 (I’m now 25) for about 4 months, and our break up wasn’t epic but certainly wasn’t pleasant. I dumped him because I was 17 and he was talking about going to college closer to where I lived so we could be *together more*, and he didn’t take it well. Fastforward four years (I was 21) to when he showed up at my place of work (a video store we both worked at when we were dating) to drop a bomb on me. See before we started dating I had logged onto my LiveJournal account to do something in front of him and he memorized my password. As you do. At that time I had locked down my LJ b/c I had vented about two friends on it and of course got into a shit ton of high School drama b/c of it. He knew that. He knew how violated I felt. And yet from that time forward (I hadn’t changed my password once since I signed up b/c I’m a lazy person) he’d been reading all my posts, even the ones I’d friend-locked/only-me-locked.
    Now I’d said some pretty not so nice things about this guy on my LJ, and I’d talked about other relationships since then, and when he told me I got the impression he’d continued to read it up to that point. You know, to check up on me. In a horrible, creepy “Nice GUY(tm)” way.” See, he still cared about me and wanted to make sure i was ok. What a dick.
    BUT his confession taught me the importance of changing my password regularly and that it was TOTALLY a good choice to dump his ass. Who knows how long I would have kept my old password if he hadn’t owned up. Nevermind that he could have NOT BLOODY WELL READ MY LJ, the dude did a solid thing by coming forward. Even if he did it for “Nice Guy(tm)” reasons.

    1. I think that story made my eyes bleed real blood.

      “I will show up at your work after reading your private thoughts for 4 years to tell you about that in the weirdest and most confrontational way possible, instead of you know, emailing you. Can I have a cookie?”

      No cookies for that guy. I love this as a cautionary tale for why you don’t write to old crushes and make them deal with your emotions, though!

      1. I know right? I have no idea what he was thinking, but I suspect he was hoping for me to swoon at his honesty. Plus it was at MY workplace while I was working which meant I couldn’t freak out and punch him in his stupid face, something he knows I am fully capable of doing. I’ve run into him since then and every time he’s like “Hi! Let’s have a super awkward conversation in public because you’re an adult and wont headbutt me for being a privacy invading douchebag. How’s school?” Best thing about moving away from home is I don’t have to worry about seeing his stupid mug at next time I go to see a movie.

        Not to be too childish but I take private delight in him reading every dismissive comment I made about his penis size, as well as the fact at that we *never* actually had sex because of this fact coupled with his eye coordination problems.

    2. Oh god I sort-of did that to the first guy I went out with. Except I didn’t have his password, I was just reading his public LJ posts from the time we were dating in an obsessive desire to find clues to what he’d been thinking at the time. Given that he had no reason to expect me to read his LJ, it was a pretty creepy thing to do.

      I’m so glad I didn’t have his password (cringe).

      I guess I can join the club of people who did and thought stupid things when they were younger and had crushes.

      1. The difference is you were reading his *public* journal, and if that guy was anything like me as a teenager, he wanted *someone* to read his posts, even if it was a current significant other. If he didn’t, he’d have locked it down, like I did. I think you can rest easy that you’re little invasion of privacy is a far FAR cry from my exes.

  5. I swear to god, a few months ago a Nice Guy I was friends with in high school emailed me to tell me he’d realized he’d been a Nice Guy and he wanted to apologize and also explain some things and also could I answer some questions about some of my behavior back then? The progression of which was kind of hilariously un-self-aware, and also made super clear that this gesture was not about me so much as about a) him wanting to make amends (most charitable interpretation) or b) him still Nice Guying but in a slightly more creative way (least charitable interpretation). Either way, it was a super weird email to get and brought up some bad feelings for me and I really just wish he’d let it lie.

    It’s great that you’ve identified the problematic behaviors you were engaging in before, LW (I mean that sincerely — it takes a lot of self-awareness to figure out the not-great patterns of behavior you’ve been stuck in). But the very best way you can make it up to this woman is to not engage in new versions of that behavior — by doing things “for her” that are actually for you. It would probably make *you* feel better to apologize and feel that you’ve worked things out, but would it make *her* feel better to have someone bring up some less-than-awesome stuff they did to her in the past? For me, the answer was definitely no.

    1. “It’s great that you’ve identified the problematic behaviors you were engaging in before… But the very best way you can make it up to this woman is to not engage in new versions of that behavior”


      Alternatively, if you feel the need to confess to somebody, it should be to somebody who might actually find this information useful. E.g, tell your next partner that you have been known to have these issues and you’re trying to work on them but that sometimes you may miss it so you’d appreciate if she called you out on them if/when they do crop up.

  6. The thing is, LW, this was in high school. High school was uncomfortable for most people, and most people did or said or thought things they are embarrassed about now. The fact that you want to contact this girl and rehash what went on in high school is, to me, a little worrying.

    Let it go. Make it up to her by not contacting her. Anything you say will be uncomfortable and weird for her. She will not think about how enlightened you are. She will think about how creepy you are, and she will tell all her friends.

    The only way getting in touch with this girl to talk about high school could EVER be at all, even-a-little appropriate is if you and she somehow come into regular contact again. In person. And at that point I think all that would be called for is some variety of, “Thinking about it now, I was so immature in high school. Sorry about that.” And then move on. No hints that you want or need an answer from her. No harping on why you were immature no long lists of what you did wrong and how you still wish you’d asked her out. Just… no.

  7. I just recently crossed paths with someone things were a little weird with a few years ago (it was a Bad Time in My Life, and her then-roommate was a frequent accomplice to my shitty behavior, SO), and some of the weirdness came up in conversation, and I had the opportunity to say, “I’m sorry, I was kind of a dick back then, I can’t believe you had to deal with me when I was acting like that” in reference to specific occasions she brought up (admitting, laughingly, that she was furious at the time but totally over it now). Then someone changed the subject and later, she and I exchanged numbers and made plans to hang out soon.

    LW, maybe you, too, will organically cross paths with this lady and *maybe* the past weirdness will come up in conversation and you’ll have the opportunity to say, “Man, I’m sorry if I ever made things weird or hard for you. I’m working on not being such a tool anymore.” Listen to what she has to say about it, and then move on and SHOW her how cool and mature and not-making-it-weird you are now. But until that happens, you have to accept that it’s a lost cause (and assume that she probably doesn’t hate you as much as you might think).


    In high school, some of my favorite memories were with this friend of mine, let’s call him Brian. Brian and I spent so much time together, and sometimes it got a little tense for no apparent reason at all, but most of the time he made me realize that I am a strong, interesting person with a few really special, unique gifts. He helped me see strength in myself. He made me confident.

    Fast forward to our 10 year school reunion. Sharing a cigarette on a beach near our old high school, Brian came clean: he loved me for all of high school. He was always afraid to tell me. The night before his SATs he sat composing me a love letter and didn’t get any sleep and bombed the test because he loved me so deeply. He realized as an adult that this wasn’t my fault, but then I was dating other people, and why not him….?

    This was one of the worst conversations of my life. Instead of continuing to love Brian as that person who taught me to make eye contact even though it made me uncomfortable, and to walk away from people who made sexist jokes about me to my face, I immediately replaced every memory with his unspoken love and the fact that his personal life was affected by bombing his SAT out of loving me too much. I felt guilt and shame. I felt like a bad friend.

    Leave it in the past. She may remember you fondly. You never know until you destroy how fondly she remembers you.

    1. That “I bombed my SATs for you” thing is a pile of grade A bullcrap. I mean, it may well have happened, but making it “for you” is just so wrong it’s offensive.

      People who sabotage themselves on your behalf without actually asking you are really bad news, because what they’re hoping (sometimes demanding) is that you make up for the damage you “caused” them. Which is such crap.

      It’s like throwing $10 down a storm drain and then turning to your friend and saying “I did that because I care about you so much! So now you owe me $10!”

      …Can you tell I’ve been there?

      1. It’s like throwing $10 down a storm drain and then turning to your friend and saying “I did that because I care about you so much! So now you owe me $10!”

        Oh God Holly have you met my ex?

        Also you are the best and I would like to give you ALL the cookies.

        1. And deceptively similar to “I’m making things less easy for myself as a side-effect of doing genuinely helpful things for you.” Not that that should lead to “So now you should do things for me!” either, of course.

        2. Simone – Everything I ever wanted knew about headgames, I learned from my mother.

          One of the many, many, many games was entitled “do someone else’s chores without asking, then guilt-trip them and/or fly into a rage at them because they forced you to do their chores.”

          1. That does not sound like a good game at all. I’m sorry you had to deal with that. 😦

      2. Yeah, this reminds me of the time my ex blamed me for his getting arrested because if I had been around to hang out with him he wouldn’t have gotten busted by the cops for possesion. He was a peach.

  9. NiceGuyIsm is a totally normal phase to go through when you’re learning the ropes of romantic entanglement. The only problem is if you get stuck there.

  10. I have to agree with the Captain. Telling her now about things is a bit of a Schwyzer – i.e. “Look, I used to be awful, but now I’m a much better person. Let me tell you in excruciating and self-absorbed detail just how awful I used to be (and also how much I enjoyed it) so you’ll be able to comprehend just how much great a person I am to have changed so much.”

    I’ve been in a sort of similar situation. I had a friend, who I loved and was also a little in love with. We had a business together. I was unorganized and caused a number of problems, made worse by my trying to fix things on my own instead of talking to her about it. Needless to say, it ended badly, and a large portion of the blame was mine. I’ve tried to contact her since to apologize; she’s made it clear that she’s not interested at all in ever hearing from me again.

    Now, If I were to continue pushing for that apology, it would be because *I* need to hear that I’m not a bad person. It wouldn’t be because of her needs; it’d be all about me me me me. And I don’t want to be the person that would make me. If, for some reason, we should ever happen to be in the same room again, I would hope that I’d be strong enough to just say “Hey, I’m sorry for what I did. I’m not trying to make you forgive me, I just want to say that I was in the wrong and I know it.”

    1. I love you forever for calling this kind of thing “a Schwyzer.” A totally tender, loving, cleansing, empowering face-jizz to you! 😀 😀 😀

      1. I should add that I didn’t mean to say that the LW is that bad – only that there’s a risk that the narrative becomes more about “look how I’ve changed” rather than “sorry for having been a bit of a dick”.

          1. It’s amazing how they turn out to still be douches, after going on for so long about how they used to be douches way back in the day but I learned I’m not like that now baby! Well, that was in between the endless self-deprecation.

            Oh the lessons I have learned. I should have listened to my husband’s feelings about Vader Ex. I gotta remember he has the perspective cause he’s not fucking them. Sigh.

        1. I think I’m quoting Oprah here, but “When someone tells you who they are, believe them.” Every time I ignore that advice (because I am blinded by sexy pants feelings) I regret it.

          1. Gah, on my very first date with my ex he told me “I’m a bit of a sociopath.” Took me five years to realize he meant it.

          2. Similarly, when someone tells you what their baggage is, believe it. I’m suffering from this one right now. (Bonus: when their baggage is all about how they can’t deal with feeling responsible for other people’s feelings, it also means you can’t talk to them about their crappy behavior without them freaking out. Weak.)

  11. Yeah, that AA step about making amends? You’re not supposed to do it if it’ll make things worse for the person you’re making amends to. For what it’s worth I think your motives are sincere, but if I were the girl I probably wouldn’t. And word to everyone who’s said she probably didn’t know (you were awkward generally, she was kind of nerdy too) and would start questioning your motives.

    Also I am recently internalizing the captain’s second lesson, so word to that too.

  12. It sounds like you’re grieving the friendship you may have compromised. I can understand tht.

    If you want to make peace without dredging up the unrequited drama (and I agree: do not do that), you could always just send her a nice and totally low-pressure note, preferably during vacation season.

    Hey, I was just thinking about high school and wondering how you were. I’m fine. Things are awesome for me now because details. I’m looking forward to excellent development. I’m planning whatever for the upcoming long weekend. I hope you’re having a wonderful summer/winter/life. Take care, and have a fantastic holiday. Best, name.

    People usually react well to stuff like that, and it gives you a way to close the book on the dysfunctional relationship you had before.

    The thing is, lots of people are messed up when they’re young, and most people don’t really hold that against their friends and acquaintances. Normal now, how’re you? is an email thing these days, and unless you were a bully or really unpleasant, it probably won’t make her uncomfortable.

    1. Sure, he could write a non-dramatic “Hey, how you been?” email, but then he’s gotta wait…and wait…and wait…for her reply, and then start reading stuff into it, like, is she really glad to hear from me or just being polite, and there we are at square 1 again?

      If he and this girl were friends, or even Facebook friends-of-old-friends, a “Hey, nice to see you here, what’s up with you?” message is not totally inappropriate? But if they’re not interacting at all for years?

      1. I think it depends on how close they actually were as friends. I’m generally crap at keeping in touch with, oh, anyone, and every now and then I get an out-of-the-blue, “Hey, was thinking about HS, here’s what’s up with me, how are you?” message and I’m generally pretty happy to see people are doing well and also haven’t 100% forgotten I existed.

        It’s the Nice Guy thing that complicates the matter. I was the girl who was the object of awkward unspoken affection for a dude (who had also just discovered classic rock and OH BOY did he want to tell me about it) and on the one hand, I’d love to know that he’s matured enough to not be that guy anymore and I’d be happy for him if that’s the case; on the other hand, after everything that went down, sudden communication after years of nothing would definitely raise my hackles a little, because the way he made me feel in high school was distinctly unhappy and not good. (Not that I fully realized that at the time, but, well… high school.)

        So: I’d say only the LW can judge if they had an actual, legit friendship with an edge of awkward, and if so, sending a “Hey, I’m normal now, what’s up?” message might not be terrible and might even be welcome! But if it was more of him making her unhappy or being a total creeper, then it’s better to just everything be.

        (And while I can’t speak for other women who were in my situation, I will say, my default assumption is that Classic Rock Guy grew up and matured because that’s what people do after high school. It sucks that I got the crappy part of his life experience, but I don’t assume it means he’s a terrible person forever, and I hope/assume that the girl the LW had a thing for feels the same about him.)

    2. This is an excellent script, I think.

      Rekindling a friendship after Awkward High School Feelings is absolutely possible, as long as you leave the old behaviour that came with it behind in favour of Awesome New Adult Habits.

  13. I am in favor of letting sleeping dogs lie! To not let them do so would be, alas, kind of a Nice Guy thing.

    Do you know why my ex was so upset after I left him? Because my telling him to his face that he had been abusive and that I was leaving him because of how he treated me ruined his personal story of being Such A Nice Guy and Too Bad Women Don’t Appreciate Me. Because it did not give him his closure and it did not go with his story of being Nice.

    Maybe it would have been less harrowing for me to lie to him, I don’t know, but I deserved my agency, and the way in which I chose to have said agency was to never stop telling the truth, even though he really, really didn’t like that truth.

    I don’t think you’re an abusive guy, Letter writer! But his behavior is an extreme end of the spectrum of Nice. You don’t always get a chance to rewrite the story, sorry- that is a symptom of power. Leave her alone, move on, get to know her again if happenstance, etc- but in the mean time, if you are really better, it’s time to take a lesson, move on and be a great guy in your relationships with others from here on out.

    You know what the worst thing is? Sometimes you will be your very very best most awesome self, and people won’t like you! Learning to accept this fact but still be your best and most awesome self is part and parcel of maturation, I think.

    1. Yep, this reminds me of the “Ethan” story a couple of questions ago, about how we don’t always get to know “WTF.” I think this is a desire that will lessen over time, and while you may not ever get “closure” (a concept I find……less than helpful), you will eventually stop feeling like you Need! This!

  14. Here’s a thought.

    Make yourself a solemn committment that, should your paths cross again – as they might, just by chance, it’s possible – you will (a) show by your behaviour that you have learned not to be NiceGuyTM (as you have, right?)

    (b) say at some point during your casual conversation about how things have been going since you last saw each other, casually and without expecting a response:
    “I was a real jerk in high school – I liked you a lot, but I don’t think I treated you very well”
    That’s all. You don’t dwell on it, you don’t have to make a point of apologising, and unless she brings it up, you absolutely shouldn’t dig into any of the ways you may have made her personally uncomfortable.
    But if you did make her uncomfortable, once, well, you’ve acknowledged it. In a low pressure kind of way.

    (c) Do not do (b) unless you can do so without thinking you deserve cookies for doing (b). You don’t.

    (d) Don’t take a response as an invitation to expose yourself further. Unless she actually says “Yes, you remember that time when you *details* “, you don’t. If she says “Yes,” or “Oh,” or “Well, most people are jerks, who’d be a teenager again?” these are all brush-off lines intended to indicate, let’s move on.

    Having made that solemn committment, well, you probably won’t ever meet again, and you’ll never get to say that. But if you want to say it for the right reasons – that you want to acknowledge that you were in the wrong and a jerk – then committing to do if you get the opportunity, might make you feel better.

    1. Yes — please accept the brush-off response. For the love of God.

      There was this guy who I went on one disastrous date with in high school, and who then spent some time following me around from class to class, failing to take no for an answer, and generally behaving awfully. Seven years later, I ran into him on a crowded bus on my college campus. He decided this was the perfect time to apologize for, and explain in great detail, his high-school behavior, and just completely talked over several iterations of “Oh, I’ve forgotten all about it” and “Well, who wasn’t an asshole at age 15.”

      1. If I had ever had any doubts about whether I was wrong to shun him, I sure don’t anymore!
      2. Around the fifth iteration of “No, really, I was a huge asshole!” I gave up and said “YES, YOU SURE WERE,” got off the bus, and walked the rest of the way to class.

      I’m pretty sure neither of those is what he was looking for out of that interaction. Don’t be that guy, LW! Or even that-guy-adjacent!

  15. This isn’t your exact situation, LW, but I have a related story:
    I dated a guy in college who said some pretty shitty things to and about me after I broke up with him, plus there were a lot of things that were slowly breaking down between us for a while before the relationship ended. I try to not dwell too much on this relationship because what I got out of it were a lot of lessons on what *not* to do in a relationship and not many happy memories. It was kind of a mess of poor communication, subtle sexual pressure, bad hygiene, gender-policing, etc.

    Five or six years later, I got an email from this guy saying “I have been thinking bout the past and realized I was a jerk in some ways, including [things I didn’t know he did/said]. I’m going to be in town next week and I’d like to apologize in person.” I let him know that I had no need to see him in person and anything he wanted to say could happen over email, although sadly I wound up running into him that week because we both went to the same huge beer festival.

    Here’s the thing: I can only assume this guy reached out to me so he could feel better about himself/get closure in regards to his actions, but it was HORRIBLE for me. I don’t like to think about this relationship, because all I do is feel angry that I stayed with this guy for the length of time I did, that I didn’t speak up when he was pressuring me for kinds of sex I wasn’t ready for, that I didn’t leave him when he cheated on me and gave a horrible excuse, that I didn’t assert myself enough the entire time. And having that email (and later, the ten-second interaction with him at the festival) brought up all of that shame I carry around for not doing things differently. He may have felt great for apologizing, but I felt like shit.

    Also… almost exactly a year later, he emailed me again to let me know that the woman he had cheated on me with had died. We were not friends and while I of course am sad that someone died young of leukemia… why on earth would you tell someone that?

    So yes, here’s my suggestion: make amends by moving forward. Decide that you won’t carry your old habits into the future. But I strongly suggest you let the past stay past, at least as far as this woman is concerned.

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