See bottom of post for pronoun disclaimer (note 1):
Jessie’s Girl has a special place in my heart. It reminds me of my husband and the time before we got together ( before he was my wife, or even girlfriend) . The song fit pretty squarely as part of the soundtrack of my life. This was because when I first met Wolsey and fell in love, Wolsey was dating my best friend Doug.
I met Wolsey when I was 17 years old and had just moved to Bellingham WA. I was a virgin, goin g to my fourth high school in 2.5 years and I had just found a group of friends to hang with. My best friends at the time was Doug and Jay.
We had met in a geeky Dungeons and Dragons game ( and this was summer of 1987 I believe). By the end of that school year (so summer of 1988) my friend had shifted from being a geek to being a stoner/punk (I didn’t, I was sort of my own thing… think older brother from Stranger Things but from a biker family but who is a geeky gamer).
The advantage of Doug and Jay shifting from geek to stoner/punk was meeting new people and one of those new people I met was a very beautiful young lady who eventually would change her name to Wolsey after we had been married for decades (original name is classified as Wolsey hates it).
Wolsey was friends with another girl named Colby and they were also in the punk scene. Colby dated Doug for awhile, and I met Wolsey a couple of times. I thought she was pretty cool, and I was attracted to her. The better part though was I felt like we could be friends.
Fast forward through teenager drama and Doug and Colby broke up and Doug started dating Wolsey. This meant I saw Wolsey constantly and we became best friends. I introduced Wolsey to Dungeons and Dragons and while Doug and Jay would play but fuck around, Wolsey and I both enjoyed the role-play, the story telling. I learned that while Wolsey looked punk as fuck (and hippy sometimes, Wolsey would float between the two) Wolsey liked reading, stories and was super creative.
Doug and Wolsey moved into their apartment together and I was there all the time. Doug would bail on us and a lot of times it was just Wolsey, myself, with others in our social group hanging out. It was fairly soon after we started hanging out with each other like that, that I fell in love with her ( him).
However, Wolsey was dating my best friend and I absolutely would not do something like try and break in on that. Funny enough the next time I was in this type of relationship situation with another woman I went the other way and not sure that it was any better a result.
Funny enough my parents both knew Wolsey well by this point and tried to get me to pursue her (him). I told them there was no way she was interested in me, and both my parents shook their head and said that Wolsey would be perfect for me (they were right in the end… damn them 🙂 ). Although I still to this day wish I had listened to my parents and done it. I didn’t realize they were right and she had a thing for me at the time.
The first time I noticed Jessie’s Girl as a song (it had been out for awhile) was when I was sitting in Wolsey and Doug’s living room. Doug had just been an asshole to Wo lsey and stomped off. Wolsey was sitting there looking annoyed and frustrated and the song started playing. That was the soundtrack of how I felt about her for a couple of years. For some reason the song kept playing that summer too, even though it had been out for a few years.
I never wanted to jeopardize our friendship though. Even with how fucked up my childhood was (or maybe because of it and what my dad did try to instill) I tried to remain the p aladin, true to my word and to my friend.
The other large part I didn’t act was that I truly truly loved being Wolsey’s friend and I never felt like I was in the “friend zone”. In fact I valued our friendship above everything and didn’t want to jeopardize that. It is why I can’t stand friend zone people and incels. The other person owes you nothing (and Wolsey absolutely owed me nothing, I was just happy to get Wolsey’s friendship).
That is how it was for nine months as my best friend (well he had sort of drifted away as being my best friend to be replaced by Wolsey) and his girlfriend lived together and I would go over and visit. As a side note, in all fairness Wolsey was interested in me, showed me several clues but I was too shy/resistant I didn’t follow up. My romantic soundtrack for that time period was Jessie’s Girl.
I do realize now as a fully mentally formed adult that the song can be problematic, but I still like it and it reminds me of when my husband Wolsey was a pretty girl dating my best friend before she ( he) usurped that spot and replaced Doug as my best friend.
A Girl U Should Know 