Given that his last few serious relationships were filled with expectations, arguments, publicity, it was a breath of fresh air to hear Serenity say she wanted to go with the flow of things. While he knew the publicity aspect would be a part of any relationship he was involved in, if he could help it he would try his best to keep it as intimate as possible these days. “I like that, going with the flow. It should be fun to date someone and maybe fall in love one day, the added pressure shouldn’t be relevant.” Regardless of what happened moving forward, it sounded like they were both on the same page. “I have a good feeling you and I won’t have any trouble having a good time together.” He said with a smirk, running a hand through his hair.

Ryan listened carefully to what she shared and nodded his head softly as she spoke. “I’ve been there. You know, for a long time I believed that I needed someone to fix me or complete me when that’s not really what it is about. I’ve learned that you have to get your crap in order before bringing somebody else in to deal with you.” He chuckled, raising the glass and kicking back his own shot of soju. “I’ve actually always found it difficult to write a song when in a relationship for whatever reason. There’s this running joke with my friends that once I write a hit song while being with someone, that will be when they know I’ve found ‘the one’ for me,” he throws up air quotes and rolls his eyes with a small laugh. Even when he wrote about relationships in his music, it was almost always from the opposite side of it instead of writing about it in real time. A part of him as an artist believed that the best art came from being alone and having some sort of battle to face and overcome.

He grinned as she spoke about her night at the FCAs. While he had a good time, he felt like he was certainly in his own bubble most of the night having not interacted with many people. “I’ve had very little interactions with Eilidh over the years, but she seems like a total sweetheart.” She was also likely one of the few female pop stars that he had not had his name attached to at one point or another over the years. “I know all about low-key. I probably only spoke with you and like four other people that night. I wanted to slip in, play my song, and get the hell out of there. I already got some unwelcome guests back in Montana thanks to that.” He said chuckling, referencing the protesters that were outside of his property the morning after his stirring performance.

The waiter returns with their drinks and Ryan thanks him, leaning back against his seat and smiling over at Serenity’s direction. “So, realistically speaking, what did you think of me all those years back when we went on that date in New York City?” He asked curiously, not really one to dwell on the past, more so just interested in what she thought of him then. He knew fully well that he could be a bit too much for some people, especially years back when he was at a different stage in life.

He had kept most of his career in a narrow line when it came to speaking out about politics or social issues. It was not that he did not support certain candidates or movements, but he tried to keep his involvement under wraps as best he could for the sake of privacy. He felt that nobody needed to hear his views or for him to get political. Obviously with the release of his latest single, that narrative has changed and he was prepared for it. It did not catch him by surprise at all. He chuckles at her comment, shaking his head as he thought of all the particular groups he upset. “Clearly I decided to piss all of those people off and then some. I probably can’t perform in like a twelve mile radius of a church.” He laughed, figuring the outcry from the right wing with the song to be a bit far fetched. “Yeah, that’s what I tried to do. I just saw so many fucked up things happening in the world that I had to take a hard look at myself and the space around me. If I had comeback with some heartbroken poor me song that would have been doing a disservice to how I truly felt.”

Ryan listened to her, realizing that he had kind of left her high and dry after that first date. While it was not purposely done, he knew he had the ability at times to be quite selfish and caught up in his own world, that was much of the reason why there was never a second date all those years ago between them. It certainly did not help his reputation as a womanizer and overall douchebag. “I have no good reason to tell you why I didn’t reach back to you for another date. I was an asshole back then, to put it bluntly. I was so caught up in myself that at times I would neglect people.” While it was not a lighthearted topic to talk about himself in a negative light, it was honest which was what he tried his hardest to be these days after years of attempting to only show his best sides to a possible partner. “It’s all in the past and I try not to dwell about things that are way out of my control. I’m just happy to be here with you at this moment and look forward to future dates with you.” He remarked with a smirk before sipping on his drink, noticing the bottle of soju was nearly done. “Who knows? Maybe this date will go further than the last in more ways than one.” He laughed, pouring themselves two other shots to finish the bottle.

He nodded his head as she spoke, knowing very well that nothing about each of their pasts can be changed whether they wanted to or not. It was easy to get yourself into a funk if you got caught up on the past too much. “Maybe our time wasn’t meant to be until now.” He smirked and finished the rest of his whiskey sour, setting the glass down to the side. He raised an eyebrow and grin at her next remark about her car, leaning forward in his seat to close the space between them. “If that were to happen, no need to worry. I can give you a ride back in the morning for it... or afternoon depending on how the rest of the night goes.” He chuckled before running a hand over his stubble.

He smiled, enjoying the fact that she seemed so open to anything and didn’t have a guard up. It was a welcomed change of pace for Ryan as he felt like he could be more open himself. “Is that so? Boy, be careful what you wish for, Serenity.” He winked at her before laughing, the only alcohol that remained was their respective shots of soju. The waiter appears shortly after, asking them if they needed any other drinks. “We’re good, you can just put it on one tab. Thank you.” He pulls out his wallet and hands his credit card to the server as he walks away. “Well, let’s finish these shots first, then get out of here and see where the night takes us.” He suggested with a smile, curious himself to see if this was just the beginning what else was in store for them as the night went on.

Ryan smiled and kicked back the shot of soju, savoring the taste for a moment. He was happy that he opened up and allowed himself to meet up with Serenity once again because this was the most content he felt in a long time while on a date. “If we somehow end up in Vegas, then we really lived it up tonight! It has been a long time since I’ve woken up not knowing where I was last.” He chuckled, grabbing his card and leaving a sizable tip on the check before standing up and adjusting his jacket, making sure his outfit looked good still. “I hope you can handle some more drinks, I think they might be needed at this next stop even more.” He didn’t give any hints of where they were going next, only smiling and winking over at her, walking a few steps away from her towards the exit. He stops and looks behind his shoulder, offering his hand out to her. “As a precautionary measure. I wouldn’t want you to get lost in a back alley, you know.” He states with one of his trademark charming, albeit a bit cocky smirks.