September 2021, Miami:

      "Finally get her settled in?" Ashley questioned as Bobby reached the bottom of the staircase and walked into the living room.

      "Yeah, she's in bed, with a wastebasket right next to her, so she won't have to get up if she feels sick," the older man responded. "She said all she wants is quiet, so I think I'm gonna go check on a couple of things at the restaurant. You're welcome to come with, if you want, we can even grab some lunch while we're there. That way we don't have to worry about the smell of food making her feel worse than she already does."

      "Usually the best plan when she gets a migraine," Ashley agreed. "When do you wanna head out?"

      "As soon as I text Zach and Zoe to let 'em know to be quiet if either of them get home from work before we make it back. So if you want to change or anything, you might wanna get to it."

      Ashley jogged to the guest room he was bunking in to take his phone from the charger, then hurried back downstairs and followed his host to the garage, climbing into the passenger seat of Bobby's steel-gray Chevy Tahoe. But what he wasn't aware of was that Bobby had a reason other than giving Aerin some peace and quiet to sleep off her headache for taking him out of the house - a reason that Aerin herself had given him.

      She had been thrilled, perhaps even more so than Ashley, when he had been invited to appear at an independent music festival in Miami over the Labor Day holiday, as it offered her an opportunity to see Bobby. The older man had been happy to offer Ashley one of his guest rooms, and, along with Aerin, Zach, and Zoe, had even come to watch his set the previous evening. And although the younger man had shown enough common sense not to attempt to bring one of his numerous female fans back to the house, it hadn't stopped him from flirting relentlessly with nearly every one of them that he encountered. Bobby had noticed that this appeared to annoy his girlfriend, which struck him as rather odd, so he had questioned her about it later as they were getting ready for bed, and learned that her hopes for getting Ashley and Aidan together had apparently hit a dead end. 

      "I swear, I don't know what the hell to do about him," Aerin had grumbled. "You know that I've tried everything I can think of, short of locking the two of them in a closet together, but he still hasn't made a move! Even when I leave 'em alone together for two days, he does squat!"

      Bobby had chuckled as he remembered her request that he call her at the tail end of Aidan's most recent visit to Nashville and claim some sort of "emergency" that required her to come to Florida, leaving her friend alone with Ashley for the last two days of her stay. Aerin had hoped that this would prompt him to make some sort of a move, but it appeared that he hadn't even considered the idea, and she was more than willing to share her frustrations with Bobby.

      "Maybe they're just not attracted to each other," he had reasoned. "I mean, I know they're your friends, and you want 'em to be happy, but just because you think they'd make a good couple doesn't mean that they agree."

      "Love, I've known Aidan for almost two years now, in one way or another, and I know damn good and well that she finds him attractive," she retorted. "Goddess knows we had plenty of conversations on the topic of hot guys before I ever even met him, and she was very clear on her opinion. And after her trip down back in February, he kinda slipped up and made a comment about her having, and I quote, 'a damn fine set of legs'. He tried to convince me that I misunderstood him, but I know what I heard!"

      She had paused after this statement, her features settling into an expression of dismay, then queried, "You don't think he's ignoring her because he thinks I'd be mad at him for hitting on my friend, do you? I know I've never come right out and said, 'Dude, you need to get together with Aidan, you'd be good for each other', but you'd think he'd be smart enough to pick up on all the hints I've given him. Right?"

      "Not necessarily, sweetheart," he had explained. "Speaking as a dude, I have to be honest and tell you that we can be kind of obtuse on occasion, if you don't tell us clearly and distinctly exactly what it is you want. So it's possible that he might not have the 'Captain Midnight Super-Secret Decoder Ring' to interpret what you're trying to get across."

      She had paused again, with a thoughtful look on her face, before wrapping her arms around his waist and leaning her head against his chest. Then, glancing upward with what he considered an award-worthy pair of puppy-dog eyes, she had murmured, "Well, do you think maybe you could try to find out for me? If he's worried about me getting mad at him for hitting on her, he's sure as shit not gonna admit it to me, but maybe you could get something out of him. Y'know, just as a fellow dude?"

      And, when she had unbuttoned his shirt and begun nibbling his neck, he had found himself agreeing to her request, if only to get on with his actual plans for the night, and had made a mental note to find an excuse to get Ashley alone at some point before they returned to Nashville. His opportunity had come sooner than expected when Aerin had complained of a developing migraine shortly before he had planned to start preparing lunch, so he had decided to take advantage of it: the only problem was that he hadn't decided exactly how.

      "Fuck, I guess I'll just have to wing it," he mumbled as he pulled out of his driveway and began making his way across town to his restaurant.

      "What was that?" Ashley inquired.

      "Just talking to myself," Bobby replied. "I do that a lot, I guess it's just one of those things you do when you get older."

      "Not sure that has anything to do with it," Ashley chuckled. "Hell, the singer in my old band was only nineteen when I met him, and he did that on a regular basis, if he didn't have anybody else to talk to. But I'm pretty certain he just likes the sound of his own voice, since it's practically impossible for anyone else to get a word in edgeways once he gets on a roll."

      "Been there, done that," Bobby laughed. "Got all kinds of T-shirts. And a couple of scars, besides."

      It didn't take long to reach their destination, and once he had parked the SUV, he led Ashley in through the side door, and gave him a quick tour of the kitchen as he looked for the shift manager. Once he located her, they spent several minutes discussing some delivery issues, and readjusting the menu for the week to use up some over-abundant items in the cooler. Once this was done, he gave their lunch orders to one of the waiters, filled a pair of glasses with iced tea, and led Ashley to the private dining room to wait for their food.

      They sipped their tea and chatted as they waited, then, once their chicken marsala arrived, and the waiter had left the room, Ashley commented, "Y'know, I have to say that it's nice to actually have time to explore a city after a show, instead of only seeing the venue, and maybe a hotel room, if it's not necessary to split immediately after to make the next show." 

      Seeing his chance, Bobby chuckled, and reminded the younger man, "You're kind of preaching to the choir here, remember? I was doing that when you were still in grade school. And there's something to be said for both sides, I guess. When you're starting out, you just wanna go, go, go; hit as many places as you can, get your music out to as many people as possible, and usually, get the hell outta Dodge before the cops get involved. At least that's how I remember it."

      Ashley laughingly agreed, and Bobby commented, "But, of course, nobody wanted to be in too much hurry to leave, cuz that kinda interfered with checking out the... 'local talent', so to speak."

      "I'm sure. If I remember correctly, didn't I read something about you guys actually having a condom dispenser on your bus?" Ashley inquired.

      "Guilty as charged. Now, AIDS wasn't a big thing back then, or at least most people didn't know if it was. But none of us really wanted to be out of commission for a week or two while the VD drugs kicked in, or to end up on the wrong end of a paternity suit. Crabs were a bit of an occupational hazard, though. Rubbers won't do a damn thing to keep those little bastards away, if you haven't figured it out for yourself."

      "Fortunately, I've managed to avoid that particular problem so far."

      Ashley was somewhat surprised when Bobby leaned forward and remarked, "Probably not from a shortage of opportunities, from what I saw last night. You had 'em flocking like a gaggle of geese. And from what I hear from Aerin, it's not much different when y'all are at home. I think she kind of worries about you getting into another situation like the one with that waitress last year."

      "Yeah, probably," Ashley sighed, laying his fork on the placemat. "I've never seemed to have the best luck with women, at least as far as keeping them goes. The longest relationship I've ever had, unless you count a couple of 'friends with benefits', was about two years, and that wasn't even in one complete stretch, because we broke up and got back together twice before we finally gave up. But lately, I've been just sticking with occasionally hooking up with two or three girls that I know I can trust, because the only one that I might want to try having an actual relationship with isn't the least bit interested."

      "What makes you think that?" Bobby prodded. "Have you asked her out, or are you just assuming? And are we talking about one of the girls who were at your house the last time I came out?"

      "No, neither of those. Chisa and I are just friends, and Sedona is dating one of my buddies. I may get my nuts ripped off if you repeat this to Aerin, but I was actually talking about Aidan."

      Bobby pretended to be surprised as he remarked, "Really? Aerin has shown me some pictures that she's taken, and Aidan is cute, I'll grant you that, but she doesn't look like the type that Aerin has told me you usually go for."

      "If you mean the bottle-blondes with the pneumatic boobs that I've had my picture taken with a billion times, you're right," Ashley informed him. "But I definitely find her attractive, and even beyond that, her personality just kind of draws me to her. She's smart and practical, but she's also creative, and she has a heart the size of the fucking state, which is a definite plus. But she also has that little bit of a wild side, which keeps her from being boring." He hesitated for a second, attempting to organize his thoughts before continuing, "She's... real, I guess is what I'm trying to say. Like I told her a few months ago, when we visited her in Missouri, it's great to finally meet a female fan who actually likes me as a person, instead of throwing herself at me because of what I do, or what she thinks she can get."

      "You did what?" Bobby blurted incredulously, causing Ashley to offer him an utterly bewildered look.

      "I said, I told her..."

      "I heard what you said," the older man fairly barked. "I just can't believe you were idiot enough to actually say it. For fuck's sake, Ash, I'm no country boy, but I was under the impression that only livestock could get foot-in-mouth disease. Guess I was wrong, though, because you, my friend, have it in spades."

      Looking more confused than ever, Ashley queried, "What's wrong with that? It's not like I meant it as a fucking insult, y'know!"

      "I'm sure you didn't," Bobby explained. "She probably even knows that. But you've pretty much guaranteed that the girl would sooner set herself on fire that tell you if she's got anything beyond a friendly interest in you. No way in hell, because she's most likely convinced herself that admitting to anything else would make you see her as one of 'those' chicks. So unless you can pull up the cojones to make the first move, I'd be willing to guess that you're pretty much SOL."

      Dropping his head into his hands, Ashley groaned, "Shit, I never even thought about that! I meant it as a compliment," Then, raising his eyes to meet Bobby's, he inquired, "But do you really think it was that bad?"

      "If you're actually interested in getting together with her, I think the only thing that might have been worse would have been if you'd walked up to her the first time she visited and said something like, 'Nice to meet you, Aidan. I'm Ashley, wanna fuck?' Now, admittedly, I've never met the woman, but from what I've heard about her from both of you, she doesn't sound like the type who'd do something that she probably thinks would ruin her friendship with you, and maybe even Aerin. So if you want any chance at all to find out if she's really into you, then you're gonna have to be the one to put yourself on the line. Otherwise, you're gonna spend the rest of your life wondering 'What would have happened if I'd done that differently?' And I've got more than my share of those, so trust me when I tell you that's not something you want."

      He merely nodded his understanding of his friend's words, and they finished the rest of the meal in relative silence, which extended through the drive back to the house. Once they entered the home, Bobby excused himself to check in on Aerin, satisfied that he had given the younger man some food for thought, while Ashley stood by the front door, gazing thoughtfully at his phone.

      "Okay, Purdy, you fucked up," he mumbled to himself. "Now you have to figure out how to fix it, otherwise you'll never know if the two of you might have a shot. But how?"

      Almost instantly, a grin spread across his face, and he began tapping on his phone, dialing a number and waiting until the ringing stopped, and a familiar voice on the other end said, "Hello. Ash, is that you?"

      "Hey there, Aidan. Yeah, it's me," he replied, as the plan began to take shape in his brain. "I've been thinking about Aerin's birthday next month, and I'd like to give her a surprise. And I was hoping maybe you could help me out."