When I was studying for my Ph.D. at Loyola University Chicago and residing in the city, my life was not too dissimilar to what you see in The Incredible Jessica James (2017).  As a practicing Catholic watching the movie, I cannot say that such a lifestyle is a good thing.  I will let my synopsis speak to the specifics of why this might be a problem.  At the same time, it does make me nostalgic for that urban existence, which has positive aspects and can be devoid of such promiscuity.  I am speaking more pointedly to a dating culture that I am quite foreign to, yet will try to navigate for you below.

What The Incredible Jessica James (Jessica Williams) is navigating is a couple of recent disruptions in her life.  The more immediate one is the end of her relationship with longtime boyfriend Damon (Lakeith Stanfield).  An ongoing struggle is the playwright’s string of rejection letters from theater companies with whom Jessica is trying to find a home for work.  With all this going on, she describes this point in her life as a transitional phase.  With the latter of these issues, she handles them by posting the letters on her bulletin board as motivation.  She also uses her talents to teach the performing arts to children for a non-profit organization, which is how she pays her rent.  With the former, she responds to Tinder suggestions by taking the guys to a bar she knows Damon frequents.  As she later admits, she is a complicated person, but that is exactly as God made us.  One evening while working with a friend of hers from the stage, Tasha (Noël Wells), Jessica is recommended a guy to go out with and have a drink.  Despite the fact that this man, Boone (Chris O’Dowd), is coming off a divorce, she agrees to meet him.  During their dinner, they make it clear that they are not over their exes.  It is not the most romantic of introductions, but it is enough for them to spend the night with one another.  This Catholic would look at such an evening as the beginning of a serious commitment, but that is not the case because they remain stuck in the past.  With those past significant others still stuck in their heads, they decide to unfollow them personally, but instead to follow the respective break-ups.  In other words, Boone will monitor Damon’s social media activity, and Jessica will do the same for Boone’s ex-wife, Mandy (Megan Ketch).  It does not sound healthy to me, but what it does is grow a bond between Boone and Jessica.  At the same time, Jessica is trying to grow her bond with her students.  The most promising one is Shandra (Taliyah Whitaker), who reminds Jessica of herself.  There is an upcoming young writer’s retreat, and Jessica is excited to have Shandra participate.  This is all set to happen when one day after class, Shandra’s mother informs Jessica that Sandra will not be attending.  Jessica is not happy to hear this news, but Shandra is coming from a family with divorced parents.  The weekend of the trip is supposed to be the same one as Shandra is supposed to visit with her father.  Not willing to let that stand, Jessica calls Shandra’s dad to make an appeal for the young lady to attend.  While Jessica’s gesture works, Shandra later opts to go with her dad, something the teacher has trouble understanding.  One of the reasons for Jessica’s attitude is her own fraught relationship with her parents, who are also no longer together.  They live in Ohio, and we see how they get along when she returns home for her sister’s, Jerusa (Susan Heyward), baby shower.  What emerges from their interactions is that none of them truly understand their urban relative, with them stuck in their suburban conformity.  Such descriptions allude to how Jessica feels about their lives, which is underscored by the book she gives to her future nephew/niece about fighting the patriarchy.  Being there also reminds her of all the dreams she had as a child, but how much they remain unfulfilled with the number of refusals she has received.  As such, she returns to New York and seeks out Boone.  They go on a real date, which leads to more of that non-Catholic approved behavior despite his misgivings.  He is unsure because they continue to hesitate about letting go of their past relationships.  This comes to the fore when she drops in on him after arguing with Shandra, only to find that he has just gotten out of bed with Mandy.  He is as apologetic as possible, but Jessica angrily leaves and heads for the retreat.  While there, she gets some advice from a playwright she admires about sticking with what you love instead of being distracted by failures.  It makes Jessica realize that she has been too hard on herself and others, which inspires her to reconcile with those she has wronged.  It starts with Boone, who she offers to let read her plays as a peace offering.  Next is Shandra, who Jessica tells to continue writing.  More good news comes in the form of Jessica getting accepted by a theater company in London.  Towards the end, we see her putting on her students’ shows, saying a final goodbye to Damon, and leaving things open ended with Boone.

Things are open ended with Boone at the end of The Incredible Jessica James because he offers to come with her to London.  Instead, Jessica uses his frequent flyer miles to purchase tickets for Shandra and Tasha.  The others suggest to Jessica that Boone is her boyfriend, but Jessica eschews such labels.  Because of this, I am not sure it is accurate to say that she has learned anything by the end of the film.  After all, it is suggested that this kind of attitude is what led to the heartache she felt with Damon.  You can call me a square Catholic if you wish, but I prefer my relationships to be a little more defined.  It is not that the Church says that casual friendships between unmarried men and women are impossible, but it is clear that they can get messy.  Movies such as this one over ample evidence as to this fact.  What we see here points to a larger societal problem that Faith partially seeks to counteract, “partially” as in it is a facet of it, but not the focus.  What Jessica admits to is being afraid of trying and failing in terms of relationships.  I can empathize with her.  It is scary to put yourself out there in the hopes of gaining the affections of someone you like.  What if that person says no?  Or, even trickier, what if you form a bond with that person and it does not work as you expect.  To that end, there is a quote in the movie from real life playwright Lillian Hellman, which says in part, “Nothing . . . will ever come out as you first hoped.”  If Jessica had some concept of God, she might have been better able to handle the disappoints this all but ensures.  It is God who is the author of our lives, not ourselves.  This does not mean things will always be easy, but He has nothing but our best in mind for us.

I am not sure I have recommending The Incredible Jessica James in mind for you, though it is not that bad.  As I have alluded to, the amount of promiscuity in it is a little too modern for this Catholic’s tastes.  What I do admire is the passion she has for her craft, so that is something.