What Might Have Been
Appears in 7 songs
The counterfactual exists in present tense — the speaker stands inside the moment of decision: wanting to cross from friendship into something romantic but held back by the cost of losing what they have. Uniquely the 'what might have been' is a future not yet foreclosed; the song inhabits the threshold rather than looking back from the other side.
Contains perhaps the most direct statement of the counterfactual register in Taylor's catalogue: 'I'm addicted to if-only.' The speaker peers into others' domestic lives and imagines alternative existences — a sustained meditation on roads not taken and lives unlived.
The speaker watches a former partner's new relationship from the outside and imagines the parallel life she might have had. The counterfactual is present tense and ongoing — she is watching someone else live the timeline she did not. 'Do you just not think about it?' is the haunting question at its centre.
A vault track about a relationship mythologised in retrospect — the suburban legend of what they were to each other, transformed into local mythology. The song romanticises an unrealised or ended connection precisely because it stayed unresolved.
The relationship exists entirely in imagination — the speaker desires someone too sought-after and unattainable to pursue. The 'what might have been' is anticipated and mourned before it has even begun. Distinct from most of Taylor's counterfactuals in that the alternative timeline was never entered at all.
The defining counterfactual song in Taylor's catalogue — the entire structure is built on 'if only'. The speaker explicitly imagines the alternate timeline where the relationship succeeded: 'If my wishes came true / it would've been you.' The mood is retrospective and wistful rather than bitter; the 'what might have been' is held tenderly rather than with resentment.
Looks back on a relationship that ended but was nonetheless sacred and real. The speaker is not mourning what was lost so much as honouring what existed — 'I was reminiscing just the other day.' The 'what might have been' register is present in the gratitude and wistfulness: the sense that this love deserved more time.