Everything's Different Now. Most of the songs chronicle Aimee Mann's breakup with Jules Shear.
I was instantly transported to that period when it seemed all my relationships were, at best, practice at what not to do to be in a relationship. The late 80s was an especially rich sexual time for me when I experienced as much fucking as I could stand, and then more. Men and women were completely open to me, so much so I actually turned some interested parties down, which for a formerly fat kid with a complex was something I never thought I'd do.
But I tried steering some of those short-term escapades into more permanent waters and one of them was something I called The Great Marybeth Romance. Marybeth was much younger than me, 18 to my 27 (ironically, I think, for as much overthinking as I engaged in about the dicrepancy between our ages--and she wasn't even the partner with whom I had greatest age difference--I ended up marrying a woman born the same year as Marybeth and who keeps me honest [whether I want to be or not]), and our coupling was the result of sharing a bed on a weekend New England sojourn to hike the snow-covered trails with another couple.
I don't remember when I first heard music from the Til Tuesday album or where I acquired it, but when Marybeth and I inevitably crashed and burned a month or so later, I played the hell out of the tape. True, some of the songs were too specific to Mann's experience for me ("J for Jules," "Limits to Love," "Long Gone (Buddy)"), but I realized yesterday how much I had taken in all those decades ago. I could sing "Everything's Different Now," "Why Must I," "The Other End of the Telescope," and "Rip in Heaven" word for word, matching Mann's voice inflection for inflection, pause for pause.
The most deliciously painful is "(Beleived You Were) Lucky" whose message I imagined addressed to Marybeth as she sat quietly in a dark room, fantasizing (so I imagined) all the things we could have been and that (for reasons I genuinely can't remember but may have been partly because of our ages) we could never be, a heartfelt and disjointed stream-of-consciousness letter she was writing me abandoned at her feet. (And the album version has the gut-wrenching shift in one word so Mann sings how life "would be fucking great.") Two years later, enough time having gone by to allow a one-night reconciliation, the mix-tape I gave her (foolish romantics still did things like that then) did not include the song, however.
The phrase "deliciously painful" is accurate as I think anyone experienced in this can attest. Even now, there is a luscious hurt composed of equal parts shame, anxiety, pride, wish-fulfillment, and any number of other terms you'd like to add that comes bubbling up at the confluence of such a song and such memories. Some people never have that experience and I simultaneously envy and pity them. It is one of those tightly-held, jealously-guarded, queasy emotions some of us have access to and, for the lucky ones, delight in. For us, the emotion of the breakup is our best memory.