I (38m) told a friend (39f) I had feelings for her twice and got rejected in my 20s. Found out a decade later she had feelings for me. WTF?

Shirley Stafford Hours
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Under the neon glow of a fast-food drive-through, a chance encounter stirred old wounds for a 38-year-old man. Years ago, as a starry-eyed 21-year-old, he poured his heart out to his best friend, Mary, only to face kind but firm rejection—twice. The ache of unrequited love lingered, fading as he built a life with his dream wife. But a decade later, a mutual friend’s revelation flipped his world: Mary had feelings for him back then. Now, he’s left wondering why she stayed silent.

This twist of fate tugs at the heart, blending nostalgia with the sting of missed chances. Readers feel his confusion, caught between closure and curiosity about a path not taken. Was Mary’s silence fear, or something else? His story invites us to dive into the messy beauty of young love, hindsight, and the roads that lead us to where we belong.

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‘I (38m) told a friend (39f) I had feelings for her twice and got rejected in my 20s. Found out a decade later she had feelings for me. WTF?’

I (38m) had a girl who I was best friends with from the age of 19 to 23. Let’s call her Mary. Around 21 I discovered I had serious feelings for her (as serious they can be in your early 20s with no dating experience). I worked up some nerve and told her how I felt. She was very kind but told me that she did not feel anything beyond friendship.

It sucked, but that’s the way life goes, and we continued on his friends. A few years later feelings got intense again, and I said the same thing, and Mary had the same response. I eventually realized two things: my feelings weren’t going to change and neither were hers.

She eventually started seeing a guy around that time and I did not feel right continuing such a close friendship with someone who had a boyfriend so I backed off and we lost contact over that year. A few years later I was at a fast food restaurant late at night and was going through the drive-through. Guess who was in the car behind me?

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I pulled into a parking spot and got out to throw some garbage away in a trashcan. I did it intentionally to see if she would notice who was in front of her, and if she would do anything about it. She ends up, pulling into the stall next to mine and saying hi. We play the “good to see you. How have you been?” conversation out. She mentions that she is no longer seeing anyone .

We chat a bit more, give her a quick hug and we partways. I get a text from her about a week later saying hi and wondering if I wanted to hang out. Stupidly, I said, yes, knowing that I still had feelings for her. We get back into the usual habit of going for drives, having coffee, etc. although it’s fun and familiar, I have this nagging feeling in the back of my mind that is dumb.

Fast forward about a month and a half and I get a text from her in the evening, asking to hang out. Something in my mind just flipped and I heard this voice inside my head, saying “if you go out, this will not end well. You want Mary but she doesn’t want you”. I put the phone down without responding to the text.

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I end up receiving a call from her about 45 minutes later and I just don’t pick up. It was a punk move on my part to not respond, but I didn’t think I had the courage to say I don’t think we should be friends anymore. I delete and block her number. Five months later, I end up in a relationship with the woman who would eventually be my wife.

The woman of my dreams and just an all-around better fit than Mary ever could’ve been. Over the course of the first year dating we talk about our past relationships and I tell her about my one-way feelings regarding Mary. My wife was super sympathetic and also very thankful because according to her, Mary must be blind to let someone like me go.

I recognize now that I had some extremely rose coloredglasses when it came to Mary, but being young and infatuated made me overlook a few significant red flags. Fast-forward a decade and my wife comes to me with a weird look on her face. She had been hanging out with a good friend of ours friend (Jess) had brought up Mary in conversation.

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The friend asks my wife if I had any contact with Mary in the last decade or so (which I haven’t). My wife says no, and gives the friend the short version of what I wrote above. Quite a few of my friends knew that I had feelings for Mary, but that they didn’t go anywhere because Mary only viewed me as a friend. Jess mentioned to, my wife that she had ran into Mary a few years ago.

My name had come up and conversation and Jess had asked Mary why we never got together. Mary says that she regretted to this day and that she did have feelings for me. I know that ending up with Mary woukd have not worked out but there is this part of my brain that wonders why she couldn’t admit it to me when I told her twice how I felt. Is it weird to be wondering this?

Unrequited love can feel like a punch to the gut, and this man’s story of confessing to Mary—twice—only to learn a decade later she reciprocated is a classic case of missed signals. His decision to cut contact protected his heart, but Mary’s belated admission raises questions about timing and courage. Was she scared to risk their friendship, or did her feelings bloom only in hindsight? Either way, the revelation stings.

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Psychologist Dr. Lisa Firestone explains, “Fear of vulnerability often keeps people from acting on their feelings, especially in close friendships” (source: Psychology Today). Mary’s silence might reflect this fear, prioritizing stability over romantic risk. Her later regret suggests she idealized him as “the one that got away” after life’s twists.

Studies show 60% of people experience unrequited love at some point, often in youth when emotional stakes feel sky-high (source: Journal of Social and Personal Relationships). For the man, moving on led to a fulfilling marriage, proving growth trumps dwelling on “what-ifs.”

Advice: Let Mary’s revelation be closure, not a reopened wound. Reflect on the red flags he now sees in her and cherish the life he’s built. Couples therapy could help him and his wife process any lingering doubts.

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Here’s what Redditors had to say:

Reddit’s got opinions as bold as a late-night coffee run, dishing out wisdom with a side of sass. Here’s what the community thinks about this romantic rollercoaster:

No-Table2410 − Perhaps she is looking at the past with rose coloured glasses as well. Projecting feelings onto her past self as part of wishing she made other choices. What 39 yr old Mary wants in a man will be different to what 21 yr old Mary wanted. You turning her down at the drive through may also have made you more appealing than you were earlier, when you were a guy she could have had at any time.. Either way everything worked out for the best.

AnonThrowAway072023 − Everything worked out as intended, and the best for all involved 

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LighthouseonSaturn − Don't waste a single second trying to figure this crap out. Not worth your time or energy, or messing with your marriage. Mary liked having you around. She liked the friendship and attention. I doubt that she seriously liked you. I think as time went on her tastes changed, life experience changed her,

and you eventually became her type. By that point, you would also have been changed by lofe and were ready to move on. Simple as that. Don't assign any great meaning to it. Real life isn't like the movies. You have found a better match for yourself.

AnonThrowAway072023 − Oh and you'd better fuckin reassure you awesome wife you are thrilled Mary turned you down so that eventually you 2 could meet. And tell her you have zero towards Mary, no second doubts, no interest in ever talking to her again.  Please.

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helendestroy − just because you have feelings doesn't mean you don't have other things going on, or that you have to want to chase them. sounds like she valued you more as a friend, and then that didn't work out anyway.

Inseminator_Rising − All you need to know is she suddenly had feelings for you after a few bad relationships. She tried to keep you on the back burner for a Plan B, but you found something better. Good on you for dodging the bullet.

ShadeBabez − Weirdly enough, I think you turning her down is what made her like you/realize she liked you. She probably thought you would always be there to fall back on.. You had the self respect to cut her off tho, I don’t think she expected that.

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Im a very strong believer in fate and if you two were meant to be together you would’ve been. Think about it, why would that voice telling you not to go come on so strongly? To make way for the real deal.. She snoozed and lost, played games and found out.

joegnar − There are people who, through a combination of being afraid of ruining a friendship and “well they’re always going to be there waiting for me to be ready” just… Don’t take the leap. Guys and girls both do it. It’s always a drag and a “what if” that lingers on later in life.

Farlandan − I had a girlfriend that I dated for about two years,   but was friends with her for half a decade before we dated.    I eventually broke up with her because I thought she was taking me for granted.  About six months later we were hanging out and I was feeling lonely so I asked if we should try it again.

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She declined and said she wanted to stay friends.  I thought that was that,   I never brought it up again. Years later I hear from multiple mutual friends (and even an one of her ex boyfriends that she dated after me.)  that she mentioned that she thought we'd eventually get back together and get married.    It was confusing. 

GoblinCat669 − I feel she is probably misremembering how she felt about you or romanticizing what it was in her head because she’s now heard you’ve moved on and are in a happy marriage and she is still single. Now she feels like the rejected one. If she really did have feelings for you and refused to tell you…idk.

Closed mouths don’t get fed. She fucked herself over. She did you a favor. From your post it seems like you’re pretty clear that you can now see it wouldn’t have been a good relationship. Best to let it go. Your wife may run out of sympathy for you in this situation.

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These takes range from “fate worked its magic” to “Mary played games.” But do they nail the truth, or is love’s timing just that tricky?

This man’s tale is a bittersweet sip of nostalgia, blending the ache of young love with the clarity of hindsight. Mary’s hidden feelings, revealed a decade too late, spark curiosity but can’t undo the life he’s built with his perfect match. Was her silence a missed chance or a blessing in disguise? It’s a reminder that love’s timing is as crucial as its spark. What would you do with a revelation like this—dwell or let it go? Drop your thoughts below!

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