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Question 141. Breakup second thoughts: Can these pants be fixed?

Dear Captain,

This is a question about tailoring ill-fitting pants.

So there’s this lady in my life. She’s a fantastic lady. I met her last summer and we connected pretty much instantly. I was coming off some serious heartbreak, she was coming off some other drama. So we took things slowly, but we started to develop feelings for each other.

After a couple months, I moved back to school and she moved back to work a few states over. I was hesitant to get into a long-distance relationship: I’d done it before and hated the logistics and the lack of face time, and I didn’t want to take things with her any faster than they’d been going. But we decided to stay in touch and see how things developed on their own.


And they did develop. We talked every day. I liked talking to her on the phone, which was new for me. We wrote back and forth. We sent each other poems and pictures and articles and random things that made one of us think of the other. I went to visit her and loved her company as much as ever. I wasn’t sure, but I thought I might be falling for her.

But then a lot happened. I had a depressive episode that lasted for a couple months. I hated my program and being a student and living in my town. I was nervous about the future. I cried a lot and had a panic attack once and felt really trapped and awful. There was a day that was the worst day of my life where I wondered what it would be like to step in front of a bus. And somewhere in the midst of that, I realized that this woman was not the woman I was supposed to end up with.

Or that’s how it felt, anyway. It was this weird, strong intuition. It felt like all the “taking it slow” had been because I hadn’t been sure if she was the right person for me, and now I was sure that the answer was “no.” And I couldn’t be with her in good conscience, knowing that, because I suspected that she didn’t feel the same way. So – trying to be as clear and kind and gentle as possible – I broke up with her. It was miserable.

She took it hard, but she understood that she couldn’t change my mind for me, and didn’t want to try. That’s not how love works, she said. And it’s not.

But I still feel that connection for her that I felt the first day we met. There’s nobody else in my life I’m interested in at the moment. (In fact, I don’t want to date anyone right now. I want some time off from the heartache, and I’m kind of a serial monogamist and feel like I don’t know who I am outside of relationships, like I haven’t built real boundaries for my self yet. This is a big deal.) We’re still friends, we still talk every day, we still love each other. I am doing my damnedest to be totally honest about my feelings and not lead her on in any way; she assures me that she knows where things stand between us and is okay with that. I’ve more or less climbed out of my depression and have just started therapy, which is awesome.

Oh Captain, is there a way to make this relationship work? Being less depressed doesn’t make my intuition about the two of us go away. I still don’t think she’s the right person for me to be with. But I want her to be, so badly. She’s smart, down to earth, supportive, gorgeous, with an incredibly beautiful soul. (Also, we’ve barely scratched the surface of our sexual potential together and that drives me crazy.) It’s just this FEELING, this not being as in love with her as I wish I were. It feels like a limit – like, I’ve reached the maximum amount I can be in love with her, and it’s not enough. It doesn’t feel like a choice. It feels like I’m not getting to be with this person because of something I can’t control. That thing just happens to be this knowledge in the pit of my stomach.

Will that ever change? I’m not quite waiting around for that to happen – after all, we are still broken up – but I’m not NOT waiting around for it to happen, either. I don’t want to get back together with her if I feel this ambivalent; that’s not fair to either of us. She deserves all the love in the world. Could I ever be the person to give it to her, or should I just give up on this? Can you tailor pants to make them fit, even if you’re not sure why they don’t? Is it possible for them to fit eventually? Will the pants size of my love change to accommodate them? In a month, or a year, or five? Does that ever happen? 

[FWIW, I'm a 25-year-old woman. She's 28. And thanks for your whole website full of amazing advice...I am a dedicated reader and lurker.]

Fix My Pants, Please?

Dear Fix My Pants:

I don’t know.

Second thoughts about breakups are part of breaking up, especially if you’re only dating really awesome people as we encourage around these parts. You can live in those second thoughts for a long time and break your own heart with them in slow motion.

The poets feel your pain:

Friendship After Love - Ella Wheeler Wilcox

After the fierce midsummer all ablaze
Has burned itself to ashes, and expires
In the intensity of its own fires,
There come the mellow, mild, St. Martin days
Crowned with the calm of peace, but sad with haze.
So after Love has led us, till he tires
Of his own throes, and torments, and desires,
Comes large-eyed friendship: with a restful gaze,
He beckons us to follow, and across
Cool verdant vales we wander free from care.
Is it a touch of frost lies in the air?
Why are we haunted with a sense of loss?

We do not wish the pain back, or the heat;
and yet, and yet, these days are incomplete.

I think the smart thing to do is to focus on therapy and climbing the rest of the way out of this depressive episode and to not stay obsessed with a long distance relationship where you were sure that “she was not the woman you were supposed to end up with” where you “still don’t think she’s the right person for you to be with.”  Listen to those instincts.  Listen to yourself in this paragraph:  “There’s nobody else in my life I’m interested in at the moment. (In fact, I don’t want to date anyone right now. I want some time off from the heartache, and I’m kind of a serial monogamist and feel like I don’t know who I am outside of relationships, like I haven’t built real boundaries for my self yet. This is a big deal.) “

There’s nobody else I’m interested in right now” is not a good reason to have a relationship with someone. “I’m trying to figure out how to have boundaries about relationships and figure out who I am outside of one” is a good reason to NOT pursue a relationship right now.

If you’ve been honest about your feelings (or lack thereof) and this lady still wants to talk to you every day, that’s her decision, but if you’re casting about for a boundary to set, the one where you both take a break from intense contact and from thinking about what might happen “IF ONLY”  sounds like a good starting point.

If you really let her go, you’ll be without a relationship prospect and a daily source of flirting, affirmation, and comfort that you’ve come to count on, and I realize that’s scary and it sucks, especially in the short-term. Expect some withdrawal. If you lived in the same place, your lives and social circles would carry you back into each other’s paths without anyone having to buy plane tickets. But the long distance nature of this thing adds layers of complication.  It’s easier to live in the second thoughts or what might happen and keep everything entirely in your head because all of it is at a distance. I think you live in your head A LOT, and I think this question of “Do I love her enough? I don’t think so. But she is so cool? Maybe I can love her? But I don’t love her as much as I should love her?” is a well-worn path your brain has traveled to death. I have this knee-jerk thing where I think if you’re debating the relationship and discussing the relationship and worrying about the relationship more than you’re HAVING the relationship, the relationship is not working and something big needs to change or it needs to end.

Trust therapy. Trust time and distance. Trust that if one lovely gorgeous cool lady liked you, another one will present herself in your life (and that your nifty ex will also be loved as she deserves by someone else). Trust that giving yourself a big old break from this line of questioning is a healthy step. Set the boundary of “Let’s not talk for a while” to give yourself that break and to prove that you can set a boundary.

Or decide that I’m completely wrong about everything!  I don’t know you!  I don’t know your love!  You’re going to call your ex-girlfriend and love the daylights out of her forever!  Where is it written that you must do the “smart” thing? Whatever it takes! In which case, there’s your answer.  But short of that?  Leave the lady alone.

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About JenniferP

Chicago filmmaker, teacher, and blogger.

23 comments on “Question 141. Breakup second thoughts: Can these pants be fixed?

  1. Fix My Pants, think about your metaphor. If it were you, would you want someone else cutting snippets off of you and stitching you into their shape, the needle flashing in and out of your substance, creating innumerable small holes? No? Then don’t do it to someone else. You would not be doing this woman a favor.

    • Daaaamn. This just says it all.

      FMPP, don’t do your ex the disservice of stringing her along in a relationship you know you’re lukewarm on. Imagine you were to overhear your girlfriend saying something like, “It feels like a limit – like, I’ve reached the maximum amount I can be in love with her, and it’s not enough.” Ouch, right???

      Let this girl go.

    • That’s what my immediate thought was — tailoring someone to be perfect for you? Noooo creepy bad! Pygmalion hardcore. ;(

  2. Wow, I am living this exact same situation. The pants are pretty damn good, a little short in the leg but nobody would notice, and I have to throw them away anyway? That is some great, but incredibly difficult advice.

    I’ll probably keep doing the unhealthy thing, but I know you are right (as usual) Captain Awkward…

  3. For a long time I was reluctant to acknowledge that “weird, strong intuition”, that one in the pit of my stomach. It smacks of GWB trusting his gut and all that. But I have come around.

    I wonder if Fix My Pants might be neglecting her local friend network. (Friend-friend, not romantic-friend.) That can be pretty depressing all by itself without the added stress of a not-quite-right long distance relationship.

    • I think you’re onto something with the “re-invest in local friendships, work, community.” Long distance relationships allow you to put that all on hold, because you’re absorbed in the magical faraway future.

      Also, Letter Writer, if you do decide to set a boundary and really break up, here’s what it looks like:

      “Ex-girlfriend, you know I think you’re the best, but us talking every day is stopping me from moving on in the way I need to right now. Can we take a good long break from that and revisit this in say, 6 months when it can be more like friendship? Thanks.”

      Here’s what it does NOT look like:

      “(4 hour conversation about feelings where you run through all of your reasoning again) + (crying )+ (asking her what she thinks you should do in the hopes that she’ll agree to maintain the status quo/have sex with you a few more times)”

      Leave out anything about doing it “for her protection” or “her good” or “being fair to her.” Do it for yourself (I need space and time to not think about this relationship for a while) vs. trying to be the good guy who is self-sacrificing. That guy is annoying.

  4. Relationships take work. But if they take alteration – and if the alteration isn’t something both partners agree to, like “You’re right, it’s much better if I talk about my feelings with you than if I bottle them up – take those pants off, they don’t fit.

    I’m going to throw in a weird outlier story about gut-trusting. I had a long-term, exclusive relationship with a dude that I loved spending time with. We were compatible in just about every way! But I just didn’t feel the love. There was a great deal of care, and romance, but when I imagined myself spending my life with this dude, I saw a marriage of convenience.

    I’m not sure why, or where these hesitations came from. I certainly didn’t suspect that he had a secret cyber life that included a submissive persona and posting casual encounter ads online. The secrecy (rather than the content of the secret) ended things between us.

    I’m still surprised, because there were no clues! But my gut knew that he wasn’t the one for me. Team Gut!

  5. I once had a boyfriend tell me he was love with woman he knew I would become, which left me to question what he thought about the woman he was currently dating.

    Remember, you can still seriously care about this woman — and if you do it genuinely, who knows what will happen? Maybe you will be great friends and maybe that would be better than being flawed lovers.

    • That goes in my top 10 most hilariously obtuse breakup lines.

    • I think we may have dated the same guy. Except I was engaged to him. Once he started telling me if he met me the way I was now he probably wouldn’t date me, I DTFA. But it still did a number on me.

  6. Team Gut! LOVE it.

    I have a theory that any important decision needs to be made with the gut. We are smart in the gut!

    I think the real info in the letter writer’s letter is in the parentheses. This feeling of wanting to be with the long distance lady is maybe about being uncomfortable being single, and wanting to explore something exciting.

    The Captain is wise: If you are spending more time agonizing about the relationship than having it, something is wrong.

  7. …BUT…is this you really talking or is your depression speaking for you ? Depression can create some pretty amazing distorted thinking about everything — especially your feelings. I suggest that you try to work through the depression, then check in with your heart again about how you really, clearly feel.

    • This is what I was going to say. One of the hallmarks of depression is not just that you feel bad, it’s that you often *can’t* feel good. You can lose the ability to feel happiness, and, I would imagine, love.

      • You both speak truth. Still, I’ve had the distinct pleasure of being dumped or almost dumped every time my partner had a depressive spike and rethought the entire relationship through the most negative possible lens. Since the relationship is long-distance, I’m still going to argue for taking a big, fat break from even thinking about it. Wear some new grooves in the brain for a while.

        • As a person who’s had the distinct pleasure of having to slap down my depressive brain every time it went, “Hey, don’t you think it’s time to rethink your entire relationship through the most negative possible lens, and have a big talk with your partner in which you dump him or almost dump him? DON’T YOU THINK SO?” I am down with the plan of telling this LW to take a long break. Sometimes it really is better to be single for a while while focusing on your own emotional health. Advantages include not wandering around in a depressive fog doing a nasty push-pull routine with a partner who cannot make you feel better, or surer, or happier. Destructive thought patterns can’t be cured with the Power of Love, y’all.

          I mean, I don’t necessarily subscribe to the idea that we have to be in “good working order” before putting ourselves out there on the dating scene, but when your instincts are dulled to the point that you just can’t be sure if you are in love or not… For me, that’s a signal that it is time to take a few months for yourself and get a little happier. Not least because as others have mentioned, gut feelings are soooo important when it comes to relationships! If the gut isn’t quite functioning properly and you find yourself constantly second-guessing, it’s way too easy to end up with someone who isn’t, in fact, good for you.

          • ““Hey, don’t you think it’s time to rethink your entire relationship through the most negative possible lens, and have a big talk with your partner in which you dump him or almost dump him? DON’T YOU THINK SO?” ”

            AAAAAAAAAAHHHHHH THE WORST

          • I agree. For certain amounts and kinds of depression, being in a relationship can actually be a huge help. A significant other really can make you happier, but it’s unfair to them to expect them to make you happy in the first place, all on their own. Ultimately that’s your own responsibility.

            So if you’re mired in that deep sort of depression that never allows you to see anything positively, then there’s a good chance it’s not a good time to be in a relationship. But that’s the kind of judgment call you have to make on your own, I suppose.

    • Take a break. Make it a real break. Don’t talk on the phone or chat on Skype. Maybe an email once every other week for a ‘this is how life is’ update. Make some time in your head for yourself and for your life. Work with your depression, and after therapy, you may find out you were wrong or right. You just don’t know who will come along when this happens. Also, there are certain exes that may always have a little hole burned into your brain because things were *Almost* right. You have to realize that almost is a slimy little word that usually speaks to core incompatibilities between people.

  8. “Almost right” sucks in a way that “right” and “completely totally wrong” don’t. It brings out the American in all of us — if you only worked hard enough at it, you could make it work. Well, if you worked hard enough, you could keep it going, but it would always be work and always be only “almost” right.

    Distance and perspective are great things.

  9. This answer is *perfect*. I feel the need to throw in my two cents because MAN I AM YOU (or I was until about two years ago, when I had a protracted falling out with my best-friend-but-actually-he’s-in-love-with-me-and-that-makes-me-feel-good-but-I-don’t-think-I-want-to-date-him-we-can-just-be-friends-and-still-spend-a-lot-of-time-talking-about-our-feelings-for-each-other person), but really, you should just listen to the Captain, who is at her finest here.

    But because I do feel the need to chime in: it’s super clear from your letter what’s going on. You say that you’re a serial monogamist who has trouble setting boundaries and really feel like you need to be alone and maybe aren’t super happy with your life at the moment (both for reasons linked to your depression, and for external reasons linked to your town and your school). Then you say that there’s a woman you like but don’t think is right for you and after breaking up with her you engage in daily angsty conversations and spend a lot of time trying to figure out if maybe you could date her because you have a great connection with her and there’s no one else you like.

    This, my friend, is so not about this woman, no matter how lovely she is. It’s about learning, as the Captain suggested, how to feel good about yourself and your life without relying on the flirty sexual-tension-filled affirmation that comes from playing will-I-or-won’t-I with a potential romantic interest. That is a fun game, and it can be an intoxicating game, and it is often a game that makes you feel really good about yourself at times when nothing else does. Because this beautiful, wonderful woman is really into you, and all the time you spend thinking about that and talking about it with her and listening to sad sad songs that remind you of it is time that you are being told “you are so great that this beautiful, wonderful woman wants you.”

    I’m sure you ARE so great. But you need to know you’re great for reasons independent of how other people feel about you. You deserve to feel good because YOU think you’re great. And unless you take some time off from flirting and dating and all of that stuff, it’s going to be really hard not to fall back on how good it feels to have a potential romantic interest rather than focusing on loving yourself.

    It’s not my column, but if I could give you any advice, it would be this: take yourself off the market for one year. Don’t just not date anyone. Don’t flirt with anyone. Don’t try to figure out who you would be interested in if you could date. Don’t read old emails from love interests or listen to the songs you shared with them or look at pictures of you with them. And it will suck at first. It will feel like you have nothing interesting going on and no emotional outlet and like your ovaries are maybe drying up and falling out and what if there are no single people left when you’re 26? But it will force you to focus on what makes YOU happy and whole and loving yourself. You will have to find ways to feel good that have nothing to do with who wants to date you. And you will find that you love your own company, and that going to the movies by yourself on a Sunday morning is amazing, and that you can forge deeper and more awesome connections with your friends when not trying to figure out which ones might be dating material.

    And then one day you will catch your reflection in a window and will realize that you look beautiful and that you’re brimming with warm, contented feelings and that you’re so proud of who you are and where your life is in that moment. And that feeling will have nothing to do with someone else liking you and everything to do with liking yourself, and it will stick with you so much longer and feel so much realer because you will have earned it the hard way instead of trying to cheat by borrowing it from someone else. Trust me when I tell you that it will be worth it.

    (And trust, as well, that the Captain is right about needing to take a real break from this woman with as little drama as possible. I really did lose my best friend by letting the romantic undertones and angsty conversations go on for far too long, and I regret it every day. That’s not an honest relationship, and it’s not one that’s fair to either person, and it really, really isn’t one that can last. And despite everyone’s best intentions to just be friends, it’s too easy to slip back into those patterns and feelings if you don’t make a clean break, at least temporarily.)

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