Single divorce attorney Alex Turner is watching reality TV when she sees her latest ex's new fiancee picking out her wedding dress. Yet again, the guy she dumped went on to marry (or at least seriously commit to) the next person he dates after her. Fed up with being the precursor to happily ever after, she decides to interview all her exes to find out why - starting with her first boyfriend. Embarking on this journey with childhood friend Will Harkness, Alex soon realises the answer to her questions might be the man riding shotgun.