Unlucky in Love: The Clueless Con

In Caffrey Disclosure, a federal marshal told Neal he led a charmed life. Neal objected to the expression, yet it's fitting in many respects. A chance meeting with June enabled Neal to live in a mansion for a ridiculously low rental fee. His serendipitous encounter with Peter in St. Louis, the second chance at a new life, and his natural abilities are a few more of the ways Neal's been blessed. But there's one aspect of his life that has missed out—his love life.

Warning for minor spoilers for the Caffrey Conversation series

I know—it's hard to believe. Neal has good looks and charm in abundance. But when it comes to romance, something always seems to trip him up. He fell hard for Kate, but she was more interested in Vincent Adler and strung him along for years at Adler's request. Ouch. That took a while to get over. Poor timing wrecked the chance of a relationship with Sara. In the case of Fiona, they agreed they were looking for different things in life.

Neal's by nature an optimist, though. And a romantic. When in Nocturne in Black and Gold, Sara asks him to give her a second chance, he wishes he could. Will this be another case of bad timing? Sara freely admits she's a master at it. Neal made the first move just as she was starting a relationship with Bryan and was no longer living in New York. This time it's Neal who is the stumbling block. He's still suffering from the virtual reality mind games Rolf devised and is convinced Sara would be much better off if she kept her distance.

Another hurdle is that they've both settled comfortably into the friend zone. That relaxed state can be a challenge to leave. Enter Cupid stage right. He's started shooting arrows their way. And I'm not talking about Mozzie. In Diana's stories, Arkham Neal and Sara have been faking a romantic relationship, and now genuine sparks are beginning to ignite for them. Back in New York City, Neal and Sara are aware that their friends are trying to smooth the way for them to date. Even as they grumble at the matchmaking attempts, they adopt some of the schemes that were used in Arkham Files.

Faking a love interest worked well in Arkham. They decide to give it a try in New York. They invent aliases for themselves. Sara cleverly realizes that a lighthearted con could be just the escape valve Neal needs. He's under no pressure to decide whether or not to date. For now, they're simply playing a game to thwart the matchmakers. The Clueless con is born.

Devising the strategy has been a delightful adventure for co-conspirator Penna and me. Arkham Neal is younger and less experienced. New York Neal would naturally chafe at his relative cluelessness. Penna had created the Darcy curse in By the Book. I wanted to continue the Jane Austen theme with the Clueless con. The movie Clueless is a modern version of Jane Austen's novel Emma. Penna suggested referencing Alicia Silverstone, the actress who played the Clueless heroine, for Sara's alias. For Neal's alias, I decided to go with a meta choice—the name of the actor who portrayed him so brilliantly, Matt Bomer. Sara bases her selection on Matthew Macfadyen who starred as Darcy in a movie version of Pride and Prejudice. In Neal's timeline, that movie was due to be released in a few months.

The outcome is by no means certain. Kate will be returning to the series. Alex is slated for a future story. Raquel has volunteered to come back. Sara also has secrets waiting to be revealed. But, as Neal said in Caffrey Flashback, he and Henry specialize in complicated. They should feel right at home.

Related blog posts:
Caffrey Conversation Meets Jane Austen
Trying new things: Meta

Nocturne in Black and Gold on Archive of Our Own
Nocturne in Black and Gold on FanFiction