Taylor Swift Songs I’d Send to Former Romantic Interests

This was originally supposed to go up last week, but all the work around painting my room white and reorganizing all my stuff meant that I never got around to it. Somehow, it feels even more fitting that this is going up on Valentine’s Day.

A friend of a friend told me about this trend a few months ago. It was a bit different because most people were picking songs for their exes. I only have one, which would make for a short list and would not be very fun, so I decided to go through all the guys I’ve had some kind of romantic feelings for in some manner since high school.

The specificity is that I had to be the one who had romantic feelings. It didn’t have to be reciprocated, the majority were not, but I had to have romantic feelings for them. Adding in the guys who liked me whom I didn’t like would have been messy and complicated. There was also the risk of guessing at people/things I wasn’t sure about but strongly suspected. Keeping things based solely on my feelings was the simplest way to go about it.

I felt weird writing this because there’s always a chance that the guys I’m talking about would read this. Even though I’ve given somewhat vague descriptions of them, I think people who know me at least decently well could guess who some of these guys are. And let’s be honest, these vague descriptions aren’t even that vague.

The Often Forgotten One -

Stay Beautiful

People who know me, including myself, tend to forget that I once liked this guy. Mostly because it was really early in my teen years and also because he left my youth group around the time that my main circle of friends was forming. Looking back, I liked him solely because he was a great guy and at 14/15, it was good enough for me.

I chose this mostly because I think there’s a lot of wholesomeness to the song. At it’s core, it’s wishing someone well and hoping they find happiness and success. While I can’t say that I’m in touch with this guy any longer, I do hope that he’s out there living his dreams.

The Awkward Teen Phase -

Teardrops on My Guitar

This one doesn’t really fit, but I needed something that encapsulated that awkwardness and angst of a first serious crush. To be honest, there is no song of hers that really captures this because I don’t know that anything encapsulates how strange of an experience that was. I can’t really tell you what kept me interested in this guy for over a year other than there being very few likable guys in my youth group when I was 15.

Ask me why I liked him and I think it boils down to him knowing how to have a conversation back at an age when guys were barely figuring out how to talk to girls. Was I far more dramatic about this than I had to be? Absolutely. But it gave me a lot of perspective and after liking this guy, I went from being an INFJ to an ISTJ. Maybe this is partially why I have issues expressing feelings now…

The One I Still Think About -

the 1

I mentioned this is my post about my favorite Taylor Swift songs, but this has always had a special place in my heart. From the moment I heard it, I knew who and what it reminded me of. Not that we were ever anything, or even close to being anything, but he was someone I could have had something with. The kind of connection you have with someone that feels so different from what you experience with anyone else. It’s that idea that one or both people could have chosen to be “the one,” and yet someone didn’t. Or at least I thought so, he doesn’t.

Of all the songs on this list, this is the one I have the hardest time sharing because I hate admitting it to myself. That somehow there’s a part of me that thinks about this from time to time. That part of me worries I’ll never find something I connect with that well or have that much chemistry with.

I think it’s the line “and if my wishes came true, it would’ve been you” that gets me the most.

The One That Was Better Off Staying Friends -

Champagne Problems

Of all the people and songs on this list, I had the hardest time matching this one up. Most of Taylor’s songs are about pining over someone, being with them, or the aftermath of the breakup. This was the only one that was about choosing to end things when someone else was really invested, and knowing that ending things was right because we weren’t a good match.

In the end, this was one of those friendships that I don’t think should have been more, hence his designation. We were good friends, there was potential, but too much about us didn’t fit and wouldn’t fit together. And of all Taylor’s songs, I think this best describes the mentality I had when I knew it wasn’t right to keep acting like things would work. I’m not sure about how exactly he felt, but I know him well enough that I think some of the lyrics regarding the guy’s response would fit the disappointment on his face the night I said we should remain friends and nothing else.

Of all the people I’m writing about, this is also the weirdest one for me because he’s the most likely to read it. Not sure how that really makes me feel but if he has an issue with it, he can text me.

The Weird Freshman Year Experience -

Sparks Fly

I love this song and I’m a bit upset that I have to relegate this to a guy who ended up asking out one of my best friends in front of me during sophomore year. It also doesn’t apply beyond the words “sparks fly.”

This is one of those things that was weird when it happened and it’s still weird to me now. I’ll never be able to explain what exactly went down but it happened once and never again. There was a guy I had a couple of classes with whom I asked to help with one of my friend’s projects. The three of us met up for dinner so she could interview him, and then he stayed and hung out with us? That was already weird, but for some reason the chemistry between us was really intense that night. I’ve never experienced anything like that again, and I’m not sure that I want to. While it was fun to have that kind of chemistry with someone to the point of clear sparks, it was also INCREDIBLY AWKWARD for me and my friends.

I mostly try not to think about this one because it still makes me feel strange and nothing will ever explain what exactly went on that night.

The Ex -

it’s time to go

Ahhh, the one that gave me a few too many choices. I had a bit of a hard time narrowing this down because I could have picked several of her blame-the-guy songs and it would have worked. Ultimately, this one actually fit the best because I did know when it was time to go.

He would never agree about this, and he’s also the least likely to see this because he’s not on social media and none of his friends follow me anymore. The chorus fits perfectly – “that old familiar body ache, the snaps from the same little breaks, you know when it’s time to go” – the moment I realized that there was nothing I could do to make things work. That his choices had caused a split that wouldn’t be fixed unless he changed, something he wasn’t willing to do. Leaving me to make the decision that he blamed me for.

It hurt, but I came out of this knowing that there was no good that would come out of having stayed. Even though it was hard to go, I went at the right time instead of dragging things out. And for that, this is the song I would send him.

(He has opinions about Taylor Swift that I don’t agree with and therefore wouldn’t appreciate this song, but that’s his problem)

The One Who Should Not Have Been -

Cold As You

Digging around for this person’s song was quite the adventure. I had to go through a few different songs about manipulation before finally deciding that this fit the best. I was kind of a toss up between this and Dear John, but the lyrics of this are far more applicable.

He was someone I should not have liked for a multitude of reasons, including the fact that he knew I liked him for years and used it to his advantage. I take responsibility for acting like I was over him on a few occasions, but we both knew it wasn’t true. Deep down, I knew he only came to me when no one else wanted to listen to him, but it was the rare time I felt like he wanted me in any way. And he did a good job of pulling away and piling on affection when he needed something.

I dislike saying that there were times when he was genuinely a good friend, but there were. The thing that tarnishes many of the good memories is knowing that he was aware of how I felt and used it to his benefit. I don’t think he feels bad about it either, but I wouldn’t know because he’s no longer in my life in any way. To think that he could do all that he did to me and show no sign of feeling bad when I confronted him, that solidified my decision that this was firmly his song.

As awkward as it was to write this, knowing that one of the guys might read it, I did have a lot of fun. It was a great reason to listen though a bunch of Taylor’s songs (not that I ever need a reason, she’s 90% of what I listen to) and find the ones that best suited each guy and situation.

It would have been a little more fun had I been in more actual relationships, but I think I made the most of what I had. Besides, it’s a whole other challenge to picks songs about guys who weren’t mutually interested.

Now the question is, if you could send a Taylor song to an ex or former love interest, what would it be?

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