Unlucky in Love: Grace’s Journey through Romance

Love is a many splendoured thing but it comes more easily to some than others and that couldn’t be more true for Grace Bailey. Although beautiful, sweet, and funny, for some reason, Grace tends to be unlucky in love.

Though when the series ends, Grace is left heartbroken, it reminds us all that there are a lot lessons that falling in love, and getting hurt can teach us. We rank some of Grace’s most important relationships, from best to worst. After all, tis better to have loved and lost than to have never loved at all.

Vanaver ‘Van’ Mainwaring
Vanaver with GraceRanking: Worst
Backstory: The romance between Van and Grace was quite the whirlwind and perhaps that should have signaled the trouble. Coming off of her break-up with Jim Flett, she meets Van almost directly after and he sweeps her off her feet. Within days they are married. However, Grace learns quickly where there’s Van, there’s also the law. Things go sour quickly when Grace discovers he used her in one of his cons.
Significance: Be wary of love at first sight. Though you can hardly blame her, coming off of one break-up and leaping into the next relationship, rarely works out. Grace didn’t take the time to get to know Van which is hardly an excuse for his betrayl, but she may have spared herself the hurt if she’d gotten to know him a little better before walking down the eisle.

Del Sutton
Del Sutton and GraceRanking: Not Great
Back story: Del comes to New Bedford to attend Honey and Max’s wedding and then decides to stick around for awhile. However, while trying to help Ollie woo Grace, he falls for her himself and the two begin dating.
Significance: Coming off of yet another break-up, this time with Judd Wainwright, Del seemed to come in at the right time. Though she moves on from him pretty quickly after their break up, making it clear that her brief romance with Del might not have been anything special, it helped Grace move on.

Judd Wainwright
judd wainwrightRanking: Best
Back story: Their back story is probably the cutest, though their relationship has a bittersweet ending. Judd was sweet on Grace from their school days but May did not approve of her. Though two reunite in their adulthood when Judd makes a very contentious wedding invitation to Grace.  They began dating shortly following the wedding.
Significance: Although their romance does not end in happily ever after, her relationship with Judd is a landmark one. Grace finally disobeys May and attends the wedding with Judd. This defiant act would kick start the beginning of Grace’s quest for independance from her mother.

Through Grace’s relationships we learn that though not every relationship is until death, it doesn’t mean they don’t have provide lessons for us to carry with us. Through her relationships and overcoming difficult circumstances throughout the series, Grace goes from timid to self-assured.


Watch some of Grace’s best moments in Wind at My Back: Season One.

Wind At My Back- Aunt Grace’s Wedding (Season 1, Episode 9) from Sullivan Entertainment on Vimeo.

Leave a Reply