AKA, “hooking up with the friend of a friend.”
Cast of characters:
"A" and “B” - married couple, husband and wife respectively. Met them five or six years ago and became fast friends almost immediately. Good people.
"Q" - hot babe. Friend of A and B going back to college.
"Me" - handsome and charming beyond anyone’s imagination. Also? Modest.
The sitch, long version: This is just for background. For the basics, skip down to “The Dilemma.”
I met Q two summers ago when she was out visiting A and B. She was funny, and flirty, in the short time we hung out (in a group setting). She’s one of those women who, at first glance, you wouldn’t call conventionally pretty, but who you realize is, in the package, when you get to know her, smoking damn hot. Strong personality, sense of humor, Has Shit Figured Out and Knows What She Wants. Pushes my buttons like a… uh… professional button pushing person. There were some mild sparks, but I didn’t make too much of it, because (1) I was in the early stages of my divorce, which was my top personal priority at the time (and which has been concluded for a while); (2) she’s an East Coast resident, and I’m a West Coaster; and (3) to be honest, “on paper” (so to speak), she’s a bit out of my league. So I enjoyed it for what it was, and she left, and that was that.
She just came back this past weekend for another visit.
A and B were busy the evenings of Thursday, Friday, and Saturday; they were committed to performing in separate events (theater and symphony). They were free during the day, but the evenings were booked. Talking to Q, they decided she’d attend B’s show on Thursday, and A’s show on Friday. That left her on her own Saturday night.
A and B pinged their social circle to see if anybody was free that night who could help show her around. I didn’t have anything solid, so I said I’d be willing if nobody else spoke up. I had no agenda based on her previous visit: I’d liked her, but like I said I didn’t take the flirting all that seriously; it was more about helping A and B, as well as enjoying a chance to show off my much-loved city to an out-of-towner. Q said sure, and out of the various options, she picked my suggestion to go to Safeco Field to see the Mariners. She’s from Boston, and the Mariners had just swept the Red Sox, so she wanted to see what this upstart Seattle team was all about. Also, the Blue Jays were in town, which gave her an opportunity to legitimately root for the hometown Mariners to beat a Red Sox division rival.
As it turns out, I spent more time hanging out with Q than I expected. I decided to see A’s play on Friday night, as it was closing weekend and the best fit in my schedule. Q was there: she sat next to me, and we enjoyed more casual flirting, along the lines of her previous visit. We all went back to A and B’s house for some post-performance decompression; A is not happy with the show and wanted to vent a little bit. While there, we talked about plans for Saturday. For example, I asked about breakfast; this was met with enthusiasm.
In the end, I wound up having breakfast with Q, A, B, and C (a mutual friend who is somewhat peripheral to this story but I’ve known him for many years so I’m giving him a letter because I don’t want to hurt his feelings even though he won’t be referenced again in the story and will never see this anyway). After breakfast, Q, A, B, and I bopped around for the afternoon, and had an early dinner at a Vietnamese place I knew about. During dinner, Q tells a hilarious story about how a famous orange-shoed Iron Chef came onto her in a bar by chatting her up, pointing over her shoulder, and grabbing her boob when her head was turned. 
Then A and B went off to their respective performances, and Q and I headed down to the ball park.
Now remember, at this point it’s not a Date. She’s a friend of a friend, someone I knew a little bit, and enjoyed hanging out with. There was lots of casual flirting, but I didn’t expect it to go anywhere.
Then we get to the game, and settle into our seats, and now that we’re one-on-one, we start hitting it off like A-Rod working from a T-ball stand.
To begin with, she starts in on the standard “boost the male ego” tactic, asking me detailed questions about the game: the rules, the players, strategy at various points (“so they won’t put on the hit-and-run because there’s two outs, right?”). She’s not at all subtle about it, and I started to wonder: is she actually working me here, for real? But it wasn’t entirely unwelcome, so I responded, and we warmed up quickly.
Then, speaking of warm, after the sun dipped below the wall of the stadium, she put on her jacket and shivered, and I offered an arm to warm her shoulders. She accepted and snuggled right in. And I thought: what do you know, she really is coming on to me. Cool. 
So between the flirting and the ball game (and it’s a fantastic game, too), we have a great time. Afterward, we call B to make sure she’s done with her performance, and walk the several blocks into downtown to meet her for drinks and oysters. On the walk, Q slips her arm into mine and continues snuggling up to me. Unfortunately, when we get to the bar, we find it’s closing soon, so we discuss options. There isn’t another oyster bar open late downtown, which leaves going to another neighborhood, or heading back to A and B’s house. Then I point out that I don’t have my car; we consolidated our rides after breakfast so we wouldn’t have to bring several vehicles downtown. If we go back to A and B’s house, either I’d need a ride home afterwards, or we would need to stop at my place to get my car. And if we do that, we might as well just go to my house, since I’ve got drinks and snacks. We don’t want to make it too much of a late night, because Q has a flight in the morning and still needs to get packed; her stuff is at A & B’s house and they need to leave by 9am to get to the airport. Still, the night isn’t over and we’re all having fun, so B calls husband A, all are agreed, and we go back to my place.
The point of all this detail is to make clear that I had no ulterior motives or long-term plan at any point. With her morning flight, it’s not like much of anything was going to happen anyway. Really, it’s just that the flirtation with Q was very enjoyable, especially because, in my mind, there were no expectations and no pressure and it’s a lot easier to just be yourself in that situation. It just sort of happened as we went along.
So we get to my house. We mix up some cocktails (Pisco sours… mmm) and fire up my home theater to watch some Anthony Bourdain, of whom Q and I are both big fans. I overhear her suggesting to A that he and B take the couch so they can snuggle together, and Q will share the loveseat with me. (So I may not have had a plan, but Q… :))
We settle in, and Q throws her legs over my lap. OK, so it’s like that, sez I, and drape my arms over her legs. She puts her hand on my shoulder. I stroke her calves through her jeans. She strokes my arm. I run my fingernails over her bare feet. She drops one foot and rubs my leg. I offer a hand on her hip and she takes it in hers and we entwine fingers.
On the couch, B falls asleep.
I slide my hand up the leg of Q’s jeans and massage her calf. She slips her fingers into the cuff of my shirt. My hand’s on her tummy. Her foot is pressing high on the inside of my thigh.
If A & B weren’t there, Q and I would have been all over each other like hot buttered monkeys.
Finally, we’re done watching our shows, and A comments that it’s late and they need to get home so Q can pack and make her flight in a few hours. She and I reluctantly disentangle. She stands, watching A & B stretch and walk into the front room.
She takes a couple of steps, I come up behind her, I take her hand and pull her around into an embrace and a fierce kiss. She absolutely melts into me. It’s clear that we want nothing more than to tear each other’s clothes off and rock bods (q.v., “monkeys, hot buttered”).
Alas, it is not to be. She really does need to get moving; the conflict is legitimate. And we’re both mature enough (in our late thirties) that we are able to engage our rational brains and overrule our hormones, and cope with the associated disappointment. Ten years ago, things would probably be different: when you’re twenty-five, and you’re horny right now, you deal with it right now, and you worry about the consequences later. The advantage of maturity is that you learn how to delay gratification; the disadvantage of maturity is that you delay gratification.
So anyway, we acknowledge reality, murmur our disappointments, and smooch some more. Then we join A & B in the front room, where they’re gathering coats. They go outside, and I grab Q and there’s more snogging. Then we separate, and I ask, “When are you coming back to Seattle?” She says, “I don’t know. Soon.” And finally, Q leaves.
I shut the door, take a deep breath, go into the back room, rub one out, and go to bed.
Next morning, I wake up, still tingly from the night before. I wonder how much of the chemistry at the end was because we were a bit loose with drink, and how much was legit. I check my email, intending to search through history to try to find a message thread I know Q had been in on, to send a “hope your trip was good” note she’ll see when she gets home. She’s beat me to it; on her way out the door, leaving A & B’s for the airport, she sent me a farewell that leaves no room for doubt she wants to see me again: “I don’t know when I’m coming to Seattle, but WHEN CAN YOU COME TO BOSTON.”
So, she’s interested, I’m interested, and I want to see where it goes.
The sitch, short version: The Dilemma.
My only real concern here is the relationship between the foursome. A & B and I are friends; A & B and Q are friends. Say Q and I hook up for a while; if it goes south and gets weird, A & B will be in the middle, and that’s not fair to them. I have no idea how much A picked up on the loveseat frottage from his vantage point on the couch, so I don’t know if a hookup between me and Q would be a total surprise, but it is a consideration for me.
I’ve never picked up a friend of a friend like this, but I’ve seen it happen to other friends, and the ramifications of divided loyalties in a breakup situation can be quite poisonous. I definitely want to avoid that; I want to pursue Q but I don’t want to risk my friendship with A & B, or their friendship with Q, to do it. Mostly, my concern lies in the area of broaching this subject with the respective parties. I’m definitely going to approach A & B: “Hey, would it be too strange if Q and I started knocking boots?” That’s not a problem. Where I’m a bit stuck is introducing the question with Q. Before we get too hot-n-heavy? Like, introductory kiss, “let’s go to dinner and talk”? Or, on the phone before either of us even makes the trip? (I prefer face to face for conversation but the long-distance thing is a wrinkle.) Or, put the brakes on when we’re half naked and sweaty?
Like I said, I’ve never been in this situation, so I don’t really know the accepted protocol. I do know that however I bring it up, if she weirds out about it, that’s a red flag. Connections are about communication, both verbal and not. We’ve got the latter (q.v., “m, h b”). If the former doesn’t work, that’s a red flag.
On the other hand, this could just turn into a booty call situation: nothing deep or serious, just periodic rumpy pumpy. I guess we’ll just have to find out.
Whatever happens, it’s certainly exciting.
