Red Flags and How To Figure Out What You Yourself Think You Ought To Do

Dear Yours Truly,

This is a first for me. I never ask anyone for advice, let alone someone I’ve never met! However, I thought it might be useful to get feedback from an impartial third party regarding my current dilemma.

The context: I ended a relationship this past spring that had lasted the majority of my “adult life” (age 20-28). This was something that had needed to happen for quite a while (at least a couple of years) but was probably the most difficult thing I’ve ever done. For almost eight solid years, my former partner and I were together pretty much 24/7, aside from work and school obligations. Due to this and my somewhat introverted nature, I did not develop very many outside friendships. To make matters more difficult, I never really stopped liking my former partner as a person. We never stopped getting along or enjoying hanging out together. We never really fought or even bickered much, so it was hard to break the habit of merely maintaining the status quo and and taking the leap of being on my own (and getting rid of the only substantive emotional support system in my life).

The catalyst was a friendship that I’d struck up with a coworker about a year prior to the breakup. At that time, I grew increasingly distant with my partner, probably due to the fact that I was starting to get a pretty big crush on said coworker. Long story short, my partner found out about the friendship and gave me an ultimatum: I needed to choose between the friendship with my coworker and staying together with my partner. It brought things to a head in my mind, and I realized that I’d been too lazy to opt out of my relationship, and would not opt in if given the choice.

The day after breaking up with my partner, things happened quickly between my coworker and I. Although I knew it would be sensible to give myself time to recuperate from this huge, life-altering event before embarking on another relationship, it proved nearly impossible to resist accepting emotional support and companionship from this person, especially after he told me he’d “fallen in love” with me some months previous.

I’ve basically been seeing this person since then, with some substantial bumps in the road, since I’m pretty ambivalent about being in a relationship at all. He continually tells me he’s “so in love” with me, and we do have the most amazing time together when things are going well. When things aren’t going so well, I would rather break up with him and not bother. There are certain things about him that really irritate me, and I’m not sure if they’re things I need to work on personally and not blame him for, or if it’s an indication that I should not be romantically involved with this person at all.

I think another piece of the puzzle that I better divulge so that you can give me some informed Advice is the fact that my former partner is fifteen years older than me, and the person I’m currently seeing is twenty years older. I don’t believe this is some sort of kink; I’m not one of those people who “only goes for older men.” But I think it does have a bearing on how things are faring thus far. There may be some deep-seated pathology tied to the fact that I weathered a series of romantic rejections from dudes around my own age prior to the long-term relationship I ended up in when I was 20 (perhaps something about how it seems less risky to be the “hot young girlfriend” of an older dude?). I hate to say that the age difference does bother me, and that I often wonder what it would be like to date someone closer to my own age. Being with an older dude sometimes makes me freak out about growing old, myself. Sometimes it even makes me feel older than I really am.

The person I’m seeing now has not had much success in relationships, and I know it would devastate him if we broke up (because he told me). In fact, I’ve broken up with him twice, but neither instance lasted longer than 24 hours because I freaked out, wondered if I was making the wrong decision, and decided to give it another shot rather than risk throwing away something valuable. This may be a pattern of mine, as I had attempted to break up with my former partner at least four times before it finally “stuck” this past spring; each time, I relentlessly questioned the rightness of the decision and then talked myself out of it.

This is going to sound silly, but another factor is that we’ve got a trip planned to go to his parents’ wedding anniversary party. I’m keenly interested in meeting his family, because I do genuinely like this person, even if I’m unsure as to whether or not I want to date him. I find myself returning to the idea that I’ll just have to wait a bit longer before I break up with him. I go back and forth, though; sometimes I catch myself making future plans with him, and they’re things I’m truly interested in seeing come to fruition, but then he’ll irritate me in some way and I’ll just find myself wondering again if I need to just break up with him.

This cycle is starting to bother me! I’m grateful for any fresh insight you may be able to provide. I often feel as though I don’t even know what I really want!

Thanks for your time.


This is a hard situation. Most people enjoy loving and being loved; having sex; etc. It’s famously difficult to say “I shouldn’t be with anyone for awhile” and then stick to it when your heart/wiener is enjoying stuff with a person. The thing that makes it easier in this case, I think, is that the person you’re with right now doesn’t sound right for you. It sounds like there is more making this non-ideal than simply the timing. I’ll expand at some length and then return to this idea.

First of all, relationships are weird. The concept of staying with one person for decades is very strange. It makes sense to me that there are people who find this concept unappealing. But even for people who like the concept and want the concept in their own lives (and I count myself among this group), it is difficult to actually accomplish. I think it’s difficult because ideally a person changes a lot throughout the course of their life, and it’s very hard to create a relationship with another person that provides the stability and continuity that is the whole point of long-term monogamy with enough flexibility and openness to allow for personal growth and change. This is what people mean by “growing together.”

I know there are successful couples who got together as young as you were when you started dating your ex. It can totally work. My aunt and uncle have been together since 8th grade and you can see they are still totally in love, and I think that’s awesome. But I do think it’s less likely to work than relationships that form when one is a bit older, a bit father along one’s life path. Your 20s are a time of such unusually action-packed personal growth and change. When I think of myself at 20 and myself at 28 they are like two almost unrelated human beings; already I can tell that me at 30 and me at 38 are not going to feel as far apart, barring some sort of horrible tragedy or apocalypse or me being dead by then or something. Change slows down as you figure out your career, as you get comfortable in your own skin, etc. At 20 I very much did not know who I was; at 29 I kind of had a handle on it. So it makes sense to me that it’s hard to stick with the boyfriend you had at 20. I don’t even want to think about what my life would be like if I’d stuck with the dude I was dating at 20; you don’t even want to know.

So first of all I think congratulations are in order: you finally left a relationship that was not bringing enough joy and positivity and fun into your life. You left something stale even though it was familiar and comforting, and that is brave and I’m so happy for you. Now you can grow and change a lot more quickly, without the cage of this relationship keeping you tied to your habits and to older versions of yourself. My old man likes to talk about “getting on the path to the truest version of yourself.” He said if we moved to California and went to grad school this would happen, and he was right. But I think about it a lot. All these different paths you could take, some of them fine, some of them bad, but some of them great and really perfect for who you truly are.

ALSO, I think it is very normal to feel like you haven’t developed a tough group of friends, after this near-decade of solitude with your ex. But it is never too late! I used to think I’d made all my friends in college and would never make another; now when I look around I see that fully half my friends are friends I made after college. One of my closest friends now I only met 3 years ago! Who knew?! There are all kinds of ways to meet people. Go to parties your acquaintances invite you to. Go to meetings of the local sea turtle society or whatever. It’s awkward but the more you go to stuff the better you get at socializing. Go to a party and ask people questions and when they are interesting ask them more questions and then suddenly you will be friends. Pick a couple existing friends and make an effort to get deeper with them. Challenge yourself to be more social than you believe you are comfortable being. Be open to overtures; be open to all kinds of random people and their weird lives; go to shows, go to events, be open and smile at people, and I really think you will eventually make some friends. All kinds of ways to expand your social circle! Go take a class or join a club. One of the friends I made post-college, I literally met her because I started going to shape note singing clubs around town, and she was there, and we were the only ones who weren’t old midwestern farm wives (exaggeration) and we started hanging out, and I LOVE HER. Such a great friend to me! These things happen. Way easier to make friends than to find the Love of your Life. And now on to the real talk, which is about how this guy is not the love of your life:

You immediately started dating someone new: this is very common, even though everyone says it is bad. You also started dating this person, be honest, kind of before you even broke up with the boyfriend. This is also totally common even though everyone says it is bad. So just speaking generally, I don’t think it is necessarily/automatically a horrible doomed thing to start dating someone right after breaking up with someone else. I started dating my old man like 2-6 months after breaking up with my previous boyfriend, depending on how you define “dating.” I feel great about it and have never regretted it. But this brings me to the first

Mitigating Factor:

You don’t seem to feel great about it! You don’t even seem to like this dude that much!!! Here’s some of the ways you describe this dude/this situation: “substantial bumps in the road,” “ambivalent,” “would rather break up with him and not bother,” “really irritate me,” “freak out about growing old,” “make me feel older than I am,” “irritate me,” “cycle,” “relentlessly questioning your decision.” To be fair you also use the word “amazing” but only in the context of “when things are going well.”

In my opinion, an actual serious good relationship never, never needs the qualifier “when things are going well.” I’ve said this before. If you have to say “when things are good, they are good!” it’s like, duh. That’s a tautology; it’s not meaningful. The real trick is for things to be good even when they’re annoying or boring or you’re fighting about something. And that is very, very, very rare, which is the reason most people break up with a million people before staying with one person finally. It is very hard to find someone with whom it is good even when it’s bad. It is the beautiful paradox of successful relationships.

If you were unproblematically happy with this dude and just felt kind of conceptually bad because you feel you OUGHT to wait longer before partnering up, I’d say, don’t worry so much! If it feels good do it. However, it clearly doesn’t feel good. It doesn’t feel good if it only feels good part of the time.

Mitigating Factor:

You are so intensely on the fence, girl! And you are expressing this by telling me you basically don’t believe in yourself. And I think that’s sad as hell and something you should try to get out from under. Believe in yourself! You’re all you’ve got in this world; you need to forge a powerful and passionate bond with yourself, your instincts, your knowledge of who you are and what you want. You seem disturbed by how you don’t trust your own instincts. You stayed for years too long with your ex even though you kept telling yourself you should leave; you keep breaking up with this dude and then deciding you were wrong to do so; it sounds like you are letting these fellows govern your actions more than you yourself would like. I understand how hard it is to resist a nice man sobbing and begging and demanding that you not break up with him, that he will be “devastated” if you break up with him, but honestly, that’s his deal, not yours. Which also makes me think of another

Mitigating Factor:

Red flags! This dude sends up red flags in my brain like crazy. I am almost out of flags, that’s how many I am waving in the air right now. A 50 year old dude, without much success in previous relationships, who is immediately “so in love” with a 28 year old girl he works with? A dude who will be “devastated” if she breaks up with him after like 6 months of dating??? I am all for grand romantic gestures, and I fully believe that you are an amazing and beautiful woman, but nonetheless from your description this guy sounds just a little bit unhinged. Or at the very least, too intense. He’s putting pressure on you that he has no right to put on you. He’s a grown-ass man, and you’re a 28 year old just getting out of the relationship you’ve been in for your entire adult life; if he were a real grownup, he would know how to gently and calmly give you space. He would know that you are at a different time in your life than he is. He would understand that you have some stuff to figure out. I don’t think dating someone 20 years your senior is automatically a bad thing, but I do kind of think that a 50 year old dude who’s never had a successful relationship and who is putting this kind of intense teenage-style romance angst on someone so much younger than him might have some issues that go way beyond your relationship, or you generally. And that’s fine, I’m sure he’s a good person! We all have our issues! I’m just saying….

Also, although I think dating someone 20 years older than you can be perfectly awesome (I know two different couples with this kind of age difference, both very awesome), I think YOUR OWN discomfort with this trend in your dating life is a red flag for me. Furthermore, it’s a red flag having to do with a previous mitigating factor, which is your self-doubt and your difficulty believing in yourself. You say you suspect you keep dating older dudes because it’s easier to be the “hot young girlfriend” category than it is to actually engage with someone at your own life-phase level or whatever. So you’re afraid of dating people on an equal footing; you’re afraid that dudes your age won’t like you; you don’t believe that you are rad and deserving of a relationship with someone that’s independent of this power dynamic. None of these things are true! And being afraid that boys your own age won’t like you or won’t appreciate you doesn’t seem like a good enough reason to date older men, to me. You should date older men if you specifically like and are attracted to older men. You should never date a certain kind of person only due to fear or self-doubt.

If your instinct is that he irritates you, you don’t totally love being with him all the time, you’re ambivalent and kind of want to be single, you’re mildly disturbed by the fact that you’ve only dated much older men, etc. etc….then I’m not sure what is your reason for staying, really. Which brings me to another

Mitigating Factor:

You feel powerless: The way you describe this situation sounds intense and I wonder if you are aware of it? Even though you yourself are telling me these things I wonder if you have really stepped back and looked at what you are saying? You are basically telling me that you feel it is impossible to break up with someone who is demanding to date you so intensely. You’re saying he loves you so much that you feel obligated to stay with him. And you’re saying that, basically, you want to break up but every time you do you then tell yourself that you are crazy and wrong, so that you can go back to doing the thing the dude wants you to do. These are your descriptions!

What I am hearing is that it is awesome to have sex with a new person and it feels good, which is totally real and normal and nothing to be ashamed of. And I am hearing that you like this guy, and that you do have some fun stuff and good times with him. And I am hearing that when someone loves you so much and puts that romantic energy out at you so intensely, it feels exciting and like you’re alive, after feeling numb for so long in this boring old relationship you’ve just extracted yourself from. All of this is SO understandable, and normal, and reasonable.

But again, to sum up the red flags: you’re ambivalent, he really irritates you, you kind of just want to be single for awhile, you’re disturbed by your tendency to date older men and you think it’s due to them seeming lower risk, which also disturbs you that you think that. This dude is somewhat intense and demanding, in terms of your emotional output, which is unfair given where you’re at in your life, and which is creepy given his age and how he should know better. He’s never had a successful relationship even though he’s been sexually active since before you were born; why will this relationship suddenly be successful for him?

And bottom line the biggest red flag of all is that this is causing you stress and you are writing to advice columns about it. If this were a positive thing in your life you wouldn’t need advice. You wouldn’t be stressed about it.

I can’t remember if I’ve written about this here before but oh well: When I was breaking up with my first real boyfriend, it took forever, for many of the reasons you describe, and also because I was inexperienced, which, even at 28, you are too! You’ve only had one boyfriend! It’s totally fine, but I think you have not had the same experience with the vast panoply of red-flag-waving dudes that perhaps other 28 year olds who have been dating a lot have had. So but anyway, when I was breaking up with my first real boyfriend, I would literally talk to myself in the mirror. “What are you doing? This guy’s a jerk. If you break up with him maybe you can get Mark to french you [editor’s note: it never happened, alas].” I’d tell myself to go break up with him, and I’d do it, and he’d cry, and we’d get back together, and I’d be a weird mixture of exhilarated (by the passionate romance drama) and oppressed (by the oppressive relationship). Finally one day I told myself this was it, I was really going to actually do it, and stick to it. And so I painted one of my thumbnails red. While I painted it, I told myself all the reasons I wanted to break up with him, and all the reasons why I’d be happier, and all the reasons why it was the right decision. I told my future self: “when you are breaking up with him and doubting your decision, look down at this painted thumb and remember all this shit I told you, and remember how mad I’ll be at you if you go back on this decision.” And it worked! I broke up with him. I looked at my thumbnail. I literally stuck to my guns only because I knew how disappointed my past self would be in me if I didn’t. We did it together, past, present, and future me! And painted thumbnail! And it worked, and we broke up, and it was awesome, and I got on with my life.

I think what you are telling me is that you want to break up with this guy but you are finding it hard to find the resolve. Maybe reading this advice will help you get to that place, or maybe you should paint a thumbnail red and remember this sad, confused, ambivalent letter you’ve written to me, and remember that this is not how a good relationship should make you feel. And remember that you deserve to find yourself on your own terms, and you deserve to take some time to figure out what you want out of life and out of a relationship. Remember that this is not about him, it’s about you. You’re sorry he’s upset, but this is something you have to do, for YOU. You aren’t his mom. You owe him nothing but regular human compassion. He has brought you some good things and shaken you out of your funk and you have enjoyed many aspects of dating him, but it’s just not going to work, and you’re sorry, and tell him to please not call you for awhile. Look at your red thumbnail and remember how good you’ll feel about yourself when it’s 24 hours from now and you haven’t gone back to him. When you’re out with a friend, or at a yoga class, or reading a book you’ve always wanted to read, or going on a trip by yourself, or months and months from now when you’re on a date with a boy your age and you’re seeing what that feels like…remember all those future times and how glad you’ll be that you didn’t waste any more time in this situation that is not really what you want.

Don’t go visit his family with him!!!!!!! If you’re going to break up with him sooner or later, I say don’t go on the family trip. It will make you feel so incredibly awkward. Them all assessing the new girlfriend, delicately asking you about marriage, who knows. Him proudly showing you off. You all the time thinking “god when am I going to get the chutzpah to ditch this dude?” It’s terrible. Don’t do it. You’ll hate it. And it will prolong the break up, because then you’ll get back from the family trip and you’ll be like, well, I can’t break up with him NOW, right after this intense family trip, I’ll have to wait awhile. And “awhile” will become longer and longer. And before you know it you’ve spent years with a dude who frankly you really are not that stoked about.

If after a year of being single and happy and figuring yourself out you are like “no, for truly I was in love with that dude from before,” then I imagine he will still be around and you can reconnect. But I really do not see that happening! GO FORTH, SISTER! Go into the world and meet it on your own terms and live your own life for awhile, and figure out what it is you really want out of a dude! For one thing, there are lots of dudes you can just have fun sexy times with who won’t put this kind of intense emotional pressure on you–find one of them, if you want to explore your sexy self without committing intensely! That is a very normal thing for people in their 20s to do with one another! Take some time to just not date or sleep with anyone, though, too, if that feels right. Eventually, after awhile of just being your solo self and maybe having sex with a couple nice guys without dating them, you can then actually date other kinds of dudes and see what it’s like! Young dudes! Old dudes! Weirdos and nerds and hunks! Dudes who want to go camping; dudes who know about wine. Dudes who do web design; dudes who love Charlie Rose; dudes who like to cook. Fat dudes, skinny dudes, dudes of all creed and color! Oh the dudes you’ll meet! Go to a hippie hot spring and take off all your clothes and sit in nature and think about the cosmos. Life is short, why add stress that doesn’t need to be there? You’re 28 years old, why are trying to make yourself stay in a relationship that doesn’t feel that awesome to you? The longer you stay with this dude, the worse are your odds of getting yourself together and moving on and changing and growing and ultimately finding a dude who actually thrills you to the bottom of your heart. Who challenges you and excites you and makes you feel good. Who you can talk to and argue with without it making you feel horrible. Who you trust, who you like, who you will stand by and who will stand by you. So many dudes are out there who could be these things for you.

If you want a life partner you need to think about that word PARTNER. A partner isn’t someone you just happen to be stuck with. A partner is someone who makes your life better, who brings out the best in you. A partner is someone you can not imagine your life without. I think it’s perfectly normal to want a life partner–I certainly want one, and enjoy having one–but that desire should not motivate you to just jump into awkward partnership with any Tom, Dick or Harry who proclaims his love for you all over the place.

You’re in an awesome spot and you’re full of potential right now. I say embrace the transitional time, embrace the huge life change of getting out of this long-term relationship, embrace uncertainty and letting yourself change in all the ways you weren’t able to before. Don’t spend another second of your life stressed out, for any reason, about this dude. There will be other dudes to be stressed out about later. And then ultimately there will be a dude who doesn’t stress you out AT ALL, and when you find him you’ll remember this letter, this dude, and you’ll laugh so hard, and that will be a great day for you!

in women’s self defense class we closed every session by sitting in a circle and chanting “I AM A STRONG AND POWERFUL WOMAN, YES!” and slamming the floor with our hands. That’s what you need to do, right this minute! You can do it literally or you can do it figuratively, but you do need to tell yourself that you are a strong and powerful woman, and then say YES, in some way, to that, to yourself, to life, to your future. YES!

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5 Responses to Red Flags and How To Figure Out What You Yourself Think You Ought To Do

  1. dv says:

    Damn, she’s good! I was figuratively nodding my head through this whole column.

  2. md says:

    You hit it out of the ballpark, YT.

  3. s says:

    holy fuck this is speaking to my current dilemma to a t. i’m also trying to break up with my stressful demanding older boyfriend and it’s fucking destroying me and i feel miserable about the whole thing. this is exactly what i needed to read to break up with him. thank you.

  4. Eileen says:


  5. Mary R. says:

    Nailed it.

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