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When Jack first met Nathan Stark, he knew that he would have his hands full competing with the man for Allison’s affections. While Allison was insistent that the relationship ended ages ago, there’s still the fact that their divorce was never finalized, which automatically gives Stark an advantage. There’s also the fact that the other man already has a rapport with Kevin and definitely is much smarter than Jack, which he’s reminded of on almost a daily basis. And while Jack keeps his bisexuality close to the vest for a number of reasons, if he’s being honest with himself, he will admit that Stark is smoking hot. What Jack didn’t realize until nearly a year in is that he and Stark were participating in two very different competitions. It turns out that Nathan Stark wasn’t competing with Jack for Allison’s affections. He was competing with Allison for Jack’s.
He is completely oblivious to the fact until Allison comes to him after Nathan had turned her down. His disappointment that she chose Stark over him is overshadowed by the confusion. When he turns Allison away - respecting both her and himself too much to capitalize on her vulnerability - he knows things will be awkward as she’s probably embarrassed by being turned down by two men in the same day, but he doesn’t expect her to go out of her way to avoid him at costs. This has the unintended side effect of having to interact with Stark more, and for the first time, Jack really sees Nathan Stark for who he is, as opposed to just thinking of him as the competition.
While Jack hasn’t been with a man since before his marriage, Nathan ticks all the boxes of someone he would have pursued back them. Looks aren’t everything, though they definitely don’t hurt, and as he actually gets to know Nathan, he realizes that the other man is someone that he genuinely likes spending time with. There are moments where he wonders if the scientist is flirting with him, but he discards the thought, convincing himself that he’s imaging things. It takes Jo asking him if he’s straight or stupid before he pauses and realizes that those moments seemed like flirting because Nathan was actually flirting with him. It also makes him wonder how much flirting that he missed while he thought they were both pursuing Allison.
It takes a weekend where he doesn’t leave the bunker to decide what he wants to do with this revelation. The first thing he does is come out to his daughter, who is completely unphased by having a bisexual father. The second thing that he does is show up at GD unannounced Monday morning and ask Nathan if he’d like to join him for dinner. The other man’s answering grin tells Jack that he made the right decision and the clear walls of Nathan’s office means that the entire town will probably be aware by noon. Jo’s smirk when he gets to the office tells him that word travels faster than he expected, but he can’t bring himself to care.
If there was anyone in town that didn’t already know by the time Jack and Nathan met at Cafe Diem that evening, they definitely figured it out when the two shared a meal without being at each other’s throats. He can’t help but be concerned when Allison walks in and then immediately walks back out upon seeing them. Despite her recent Houdini act, he and Nathan both still need to work with her and she has the ability to make their professional lives very difficult. Nathan reassures Jack that she just needs time and that being vindictive isn’t in her nature. Jack decides to trust Nathan on the subject given that he has first hand experience, but he also won’t be letting his guard down any time soon.
When Nathan seems at just as much as a loss at how to act at the end of dinner, Jack definitely feels better about his own nerves. While he definitely wants another date with Nathan, he also doesn’t want to continue to feel like he’s in a Petri dish with the entire town gossiping about his personal life, so he suggests trying a restaurant in Portland that he’s heard good things about. Nathan raises a suggestive eyebrow before asking if Saturday night works and telling Jack that he’ll pick him up.
Jack can’t help but be nervous when Saturday comes, and Zoe’s light-hearted ribbing at his anxiety over what to wear doesn’t help. He finally settles on something, but only after both Zoe and S.A.R.A.H. assure him that it doesn’t look like he’s trying to hard. Given that he’s never seen Nathan in more casual dress, his jaw nearly drops when the other man arrives to pick him up. The jeans that Nathan is wearing are tight enough to be a test of Jack’s self-control and part of him wants to suggest skipping dinner and going straight to the metaphorical dessert. He’s pretty sure the only thing stopping him from making such a suggestion is that his daughter and house are both listening.
Jack doesn’t say much on the drive into Portland, though the silence isn’t awkward, and Nathan’s smirk says that he knows exactly the the effect that he’s having on Jack. Nathan’s influence and wealth means that they’re taken to an isolated corner booth of the restaurant where Nathan sits close enough to Jack that their legs are touching. He does give Nathan a warning look when he feels a hand on his knee, as he doubts either of their careers can survive an accusation of public indecency. Fortunately dinner passes without incident, though as soon as they’re outside, Nathan pulls Jack into a passionate kiss and says that he booked a hotel room nearby, just in case. And while Jack complains that Nathan plays dirty, he’s also very much on board with the plan. Given that dinner was essentially extended foreplay, they end up in bed pretty much the second the hotel room door closes behind them, and it was definitely the best sex that Jack has ever had. He’s not entirely sure where things with Nathan go from here, but he’s definitely looking forward to finding out.