He chuckles at her comment, tapping his chin as if he had to think over letting her see him again. "You know, why not? Why wouldn't I allow you to see me again? I can definitely show you off anywhere we go." He added with a laugh, resting his elbows on the table, folding his hands on a side of his face. "A watch could be very expensive. I've bought watches as high as half a million dollars or more, granted those are vintage or custom-made watches. When you're a watch person, the little details like the bezel or dial can make the difference from a watch costing 30,000 and over a 100,000. I'll stop right there though, if you let me I can go on for hours about watches. I wouldn't want to bore you just yet." He reassured her with a soft chuckle.

"Now who could ever say that? You're quite the interesting young woman, Isabel. Although watching paint dry can be fun too" He chuckles, listening to her mention the technology age she comes from. "Well you were born like in 92, by the time you were 10 years old the world was already dominated by technology. If I was born in the generation you were born, I would not be a musician right now. I would've just been all my teen years online all the time, watching porn." He stated with a soft laugh, shrugging his shoulders. "Your younger brother is a fan of fire, huh? Your father might just chase me with a baseball bat and your brother could set a house on fire. What have I gotten myself into?" He asks her jokingly with a grin.

Ryan laughed softly, nodding his head. "Fine, no more talking about that." He listened to her speak about how she keeps her brother active, taking hold of his scotch and drinking a sip from it. "Yeah, it's really tough in this generation of young kids to be kept away from technology. I went through a phase of thinking the internet and Twitter were amazing, the latter of which is mostly just coated in bullshit. Not knocking anyone who uses it these days, but I'm wise enough now to know it's not for me." He scoffled with his hair a little, smirking at Izzy. "On the bright side you don't seem crazy yourself, so I can put up with the other characters in your life. Trust me, I've been involved with some batshit crazy women in the past."

"No, that's actually refreshing to hear in the days of people reading books on iPads and Kindles. If it makes you feel equally as cheesy, I do the New York Times crossword puzzle before bed sometimes." He tells her as he chuckles. "Technology has its advantages, but like most things in life, every good thing about it means another bad one as well." He sets his scotch down, smirking over at her when she references se drank her glass of wine. He ponders the question when she asks him about his family and how they were like, his eyes falling a bit to the table before him, soon looking back at Izzy. "My family is pretty laid-back. It's very rare you get them all together in the same room, that hasn't happened in years and I haven't seen some of them in a long time with living in different places. Most of them live down in Florida, including my mom who's probably who I keep in-touch with the most. I'm an only child, so not a huge immediate family. When I was growing up it was mostly just my mom, my grandma, and me."

"Well, do you think we really fall under the rockstar realm? It's more like innocent popstar and sensitive singer-songwriter. The latter of which I've read some reviews call me that for some reason." He added with a laugh, catching glimpse of her giggle which he started quite endearing. "That's actually a very good way to put it. There we go. You now know my secret with women, just let them do what they want to me." Ryan chuckled, thinking back to his women-led household when he was growing up years ago. "I don't know what else to say about them, really. Obviously I love them, their my family, I see them every once in while. But you live not far from your family, so you see them much more often than I see my family." He paused for a moment, thinking of how to phrase his next point. "I'm of the mindset that everyone reaches a certain age or point in life where it's time to build your own home and set your own roots on the ground. That's not implying that you should neglect your family, but just that priorities shift to your own life. It's not the same way for everyone though, just personally for me that's my belief."

"I'm a super sensitive, yet strong man. I can write a song for the ladies, but I can also rock your face off with a guitar solo. And that's how I describe myself to people." He jokingly told her, laughing slightly. "That is correct too. I was very much raised with the values of women being just as equal as men are. People can write whatever they want about me on some stupid tabloid magazine, but no woman is running around this world saying that I ever disrespected them." Ryan nodded his head as she spoke, adjusting the watch on his wrist, but still listening closely to her. "That's something I can respect, obviously you have a good relationship with your family and are close with them. That's special. Tell them that I promise not to keep you in Montana too long." He tells her with a sly smirk and a small wink. "Yeah, maybe. As I said, it's not for everyone. I know some people who are close with their family all their lives. I'm not saying I completely disconnected from my family, you could never lose that part of the lessons and upbringing you get from your family. I just learned it was now my time to live as my age calls for. He takes a short pause, grabbing the bottle of wine and refilling their respective glasses. "While dating a 20 year old, of course."

"I've learned in my time as a member of this crazy entertainment industry, that not every attractive woman you run into or how famous they, necessarily means that they are wise or can sustain a substantial conversation. I've just been looking enough to run into women who do posses those quality, while being stunning. You're the perfect example of that." He said with a smile. Clearly no matter what changes occurred in his life, there was always going to be a charm in his personality that he would use with women. "Now I don't think all the ladies want to be with me, I'm more of an old story these days." He told her with a small smirk. He really didn't see himself as a big name in music or the celebrity world, whether it was just a personal theory or the reality didn't bother him. "I honestly prefer an independent woman. I enjoy being with someone who can trust me enough to the point where we don't need to be talking 24/7 or tell each other what we're doing every second of every day. It's lovely for a woman to cook for me, but I don't need that. It's not the top thing on my list of partners." He laughed at her questioning of him. "I'm just thinking, dear. You haven't been to Montana and I'm a resident of Montana, so. It's almost the perfect reason to make a trip out of it." Ryan added with a small chuckle, despite still in the middle of their first date, not thinking he would have a problem to take her to Montana one day. "Gotta stay young one or another, right?" He added with a grin, before taking a sip of his own wine glass. Just after he states the fact she's starving, he catches the waitress coming to their table with their respective meals. "I'm guessing they heard you, Iz."

"I'm just preparing you, honey. I'm always going to be complimenting you." Ryan took another sip of his wine, setting down on the table as he listened to her. "There just needs to be a good balance. I don't think anyone wants to feel as if they can't breathe in a relationship because the other person is constantly badgering. When you see someone who's in this industry, technology plays a part in keeping the spark alive when you're apart. I've been there with the late-night phone calls and iChat dates." He assured her as he thought back to how most of his past relationships, distance played apart in them, sometimes the demise of them. "I'll grab a 12 hour flight if it meant being with the woman I'm seeing for just a day to spend together." He chuckled at her, a smirking creeping at the side of his lips. "I'm sure you'll like it. It's as different as Los Angeles is." Ryan folded his arms on the table as he kept his leaned position, smiling and thanking the waitress as she places their respective meals on the table. "Thank you. You're right on time, my date over here was already thinking about eating me if that steak didn't arrive soon."

"I think the compliments are easy to come upon when you're such a lovely soul, it's no task or anything." He nodded his head, leaning his head against his knuckle. "You know, not saying you're my girlfriend yet, but if you were, as a boyfriend I'd say I'm full of surprises." He tells her with a small smirk. "Yeah, trust me, I know what you mean. I'll just say I'm not the texting type very much. I'll do it, but I'd rather just call you." He chuckled at her joke, putting his napkin in his lap, takin his knife and fork, cutting a small piece. "Bon appétit," he tells Izzy with a grin before taking a bite of the steak.

"Okay. How does girl I see regularly sound? That would still include surprises, I'm sure." He told her with a chuckle, before shaking his head. "No, no. I know how to text. I'm turning 36 in a few days, not 76 years old. Thank you very much, Isabel." He laughed a little, turning his gaze to his steak, cutting a few pieces, swallowing them down. "I told you this was the best steakhouse in Los Angeles. I like to think of myself as a man who knows where the best steakhouse is everywhere I've been." He told her grinning, then taking a few more bites, swallowing them down before speaking again. "What are you currently up to career wise? I know about the clothing line, I'm still waiting on that scarf by the way."