Note: For the rhetorical purpose of this blog post, I'm supposing that the "you" possesses a cis female body, like me. You'll have to make adjustments if you are cis male-bodied or other-gendered.
I have spent waaaaaaaaaaaay too much time thinking about this, and:
If you took Harold Finch to bed, you'd probably have to go to his place, because he has all the pillows on his bed the way he likes them, so that his neck doesn't hurt. You'll have to be on top, but that's not a bad thing. He has chronic pain, so he won't really like you to put your hands on his chest and press down hard, so he'll hold your hands instead. Finch will let you do your thing and come three or four times before he does. He might let you sleep snuggled up next to him if you don't wiggle around a lot - you have to be aware of his injuries. Of course, if Finch likes you, he will go to extreme lengths to make you happy.
Nathan Ingram would be happy to follow you back to your place, and he could probably teach you a few things. Make sure he uses condoms, 'cause you don't know where Nathan has been. On the other hand, Will Ingram knows relatively nothing, You have to teach Will things, but the good news is he's really eager to learn. Nathan has to leave right away - he has an early meeting tomorrow, or so he says. Will will spend the night, and in the morning, he knows this diner where they make awesome frittatas, if you wanna go.
John Reese is a little amazed that you think he's good enough to take to bed with you. He's so wracked with self-loathing, you might see tears in his eyes 'cause he's shocked you care enough to touch him. This doesn't mean that he'll be passive, though. If you let him be on top, you might be sore the next day. He'll be a little bit sorry about that, so he'll make you pancakes, but then he'll be up in the wind. Note: make him shower first, lest the smell of his hair gel drive you crazy. Don't expect him to sleep with you, either: he's more likely to stand guard at the foot of the bed. He's immediately and stubbornly loyal to you. If you ever got into trouble, he'd have your back.
Joss Carter would not take you to bed on the first date, or the second, because she's a lady. She wants to get to know you first, make sure you're safe to bring home, 'cause not just anybody can get anywhere near her baby. If she comes back to your place, she'll be a little shy at first. She's been hurt before and she's cautious, so take your time. After some relaxed conversation and perhaps a glass of wine, when she takes her clothes off, you're simply amazed at what a goddess she is. Be kind to her, make sure she comes before you do, and make her pancakes the next day.
Lionel Fusco will have you over on one of the weekends his kid is at his ex's place. He strikes me as the type of guy who really loves oral. He'll go down on you, and you'll probably like it, and if you're lucky you'll come, but he's really just trying to get the obligation of out the way so you'll go down on him. When you do, he's very appreciative and not put his hands on your head and try to direct. You're not getting pancakes, but you won't be disappointed that you spent the night, either. Yeah, after that first session, he might have turned on the TV and watched ESPN long enough to catch a few scores, but admit it - that second round up against the bathroom counter was surprisingly - amazing. Note: Do not bring up the words "ball gag."
The guy who'd put his hands on your head and direct is Anthony "Scarface" Marconi. Scarface is a sociopath. He'll dress you in his high school football jersey and handcuff you to the old, non-functional radiator in his shitty apartment and duct tape your feet together. It's weird, but you're kind of into it as he aggressively fucks your face. He'll take off the cuffs and hand you a beer, but leave the duct tape on, 'cause later he's gonna throw you over the back of his shitty couch and get you from behind. You'll come, hard, but his apartment's way too much of a dump to make you want to spend the night.
Your other basic psycho is Root. I think she'd surprise you by being all soft and feminine. Then she'd pull out her favorite harness and strap-on, help you put them on and want you to fuck her in the ass while she calls you Harry. She'd sleep on top of you, curled all around you like a vine, and be offended when you wanted to get up and take a shower 'cause how dare you want to get her scent off you? Try not to piss her off too much. If she wants you to put on her dirty panties before you leave, just do it. Just put up with the weird messages she leaves on your phone until you get fed up and block her number.
Kara Stanton would have to be the boss. She'd march you into the shower, make you use a certain body wash and give you special washing instructions. Then she'd take you into the bedroom and show you her sex drawer because, damn it, if you can't handle this she can damn well take care of it herself. She'll show you where she keeps the dental dams and which lube is her favorite, then act like she's just going to lie there and let you do all the work, but really, she wants to give you directions. After she comes for the fifth or sixth time, she's going to fall asleep, so you might as well sneak out while you can. If you stay until morning, she's just going to give you very specific instructions on how to make her breakfast in bed.
Root shaves. Stanton waxes. Alicia Corwin? Full-bush natural beauty.
Mark Snow would not let you have any of his coffee in the morning, and would quite possibly send you out on a mission to kill the last girl he slept with (which was probably Kara Stanton). Secretly, Snow is really grateful for your attention, but he doesn't want you to know that because he sees it as a vulnerability. He masks his feelings with a subtle, low-key hostility. If you wanted any kind of a relationship, this would be a bad thing, but in a one-nighter, this translates into pleasantly rough sex.
Zoe Morgan is all about getting it done. She considers it an insult to her womanhood if you do not come at least three times, but by the end of the night she'll have finished off rather more of your good Scotch than you'd hoped. Zoe's not into toys; she is perfectly happy with just your mouth and your fingers. She gets restless trying to fall asleep in your bed and finally you just tell her you don't mind if she leaves, really. When she kisses you goodbye, she makes you feel like the single most important thing in the universe, and you know you'll be keeping her number for future reference.
Carl Elias is a complete and utter gentleman; he's treated you precisely the way he wishes his father had treated his mother. He doesn't mind if you run your fingers over the scars on his hands, but he really doesn't want to talk about them. After making out with you for a ridiculously long time in the back of his car while Marconi drives you around and around the block, you state that yes, you will come up for a glass of wine. You have to make the first move, because he doesn't want to rush you. After all this, you might expect him to be overly cautious and too gently, but he surprises you by being completely passionate and totally into you.
Nicholas Donnelly will call you up in the middle of the day while you're at work and tell you to close and lock your office door, and proceed to talk you throw the most mind-blowing phone sex you've ever had. Bill Szymanski, on the other hand, will answer his cell phone during dinner, never take off his socks, and tell you he's going out for a cigarette as you're falling asleep and then never come back. Szymanski would not get a second date, but Donnelly? Regular booty call, on the speed dial with Zoe.
What do you think? Did I get anybody completely wrong? Did I miss anyone important?