A/N: Vigilante AU.
Long after Ruby's birthday party was over, Qrow offered to take Penny back to Vale. The car ride was pretty silent until Penny suddenly broke the silence.
"I don't like lying to Ruby. I really care about her, and I don't want our relationship to have any dishonesty." Penny said frowning.
"I'm really sorry I put you in that position, kid. I mean, I told your dad not to tell you. Besides, it's not really lying, it's keeping a secret. And this secret is for everyone's safety." Qrow replied.
"I suppose that's more...logical. I wouldn't want Ruby's safety to be compromised." Penny agreed.
"Neither do I." Qrow said.
"Why do you do what you do, if I may ask?" Penny asked.
"I, uh, couldn't save someone I loved, so to make up for it I save everyone else." Qrow told her.
"Was the one you couldn't save, Ruby's mother?" Penny asked shyly.
Silently, Qrow nods, gripping the steering wheel tightly. No one spoke for the remainder of the car ride. Qrow drops off Penny then goes home. After he flops face first onto his bed, he hears his phone ding. Digging it out of his pocket, Qrow saw that there was a notification from that dating app Yang and Nora made him sign up for. Seeing that there was a reply to the message he had sent to his match, he abruptly shoots up into a sitting position. Clover, who was Qrow's match on the app, had sent, "Hey😉.".
"Holy sh*t, he actually relied...I-I didn't think he'd be interested. Is he really interested? Why is he interested? I'm such a f**king pathetic loser, why would anyone in their right mind waste their time and energy on me?" Qrow rambled to himself.
His hands shook, he couldn't decide if he should say something or not. For a long time, Qrow has been telling himself that he shouldn't date, he shouldn't get close to people, that it was the only way to keep others safe. But on the other hand, Qrow was sick and tired of being alone, he wanted the warmth of someone's embrace. He wanted someone to make him feel like he was worth a d*mn, that he was worth being loved. Before he could fall further into the rabbit hole that was his mind, another ding came from his phone.
Clover: I hope this doesn't seem too forward, but...you're quite handsome, and I would really like to get to know you. If that's alright with you.
Qrow blushes at the message. This Clover guy was truly willing to give him a chance...maybe he should do the same for him.
Qrow: Yeah, we can talk. But, I just got home from visiting some family in Patch and I'm really tired. So, can we talk tomorrow?
Clover: Sure, that's fine with me.
Smiling, Qrow exits the app then sets his phone down on the nightstand. As he settled into bed, Qrow couldn't help but feel butterflies in his stomach.
"Just don't get your hopes up too high." Qrow told himself.
Robyn comes home to find her roommate on the couch with a goofy grin on his face, looking at his phone.
"What's up, Clover?" Robyn asked him.
"Remember that dating app I signed up for? Well, I got matched with this guy and well..." Clover replied before showing Robyn the picture of his match, Qrow.
"Wooowwww, he's hot!" Robyn said.
Clover looks at her confused by her statement.
"Dude, I'm a lesbian, not blind." Robyn chuckled.
"Are you gonna talk to him, or just gawk at his profile pic?" she asked.
"I'm gonna start talking to him tomorrow. Right now he's in bed." Clover told her.
"Ooh, if you two hit it off, you could totally double-date with me and Fiona." Robyn said excitedly.
"Haha, fingers crossed." Clover smiled, crossing his fingers.
Over the course of the next two weeks, Clover and Qrow talked to each other frequently. The more they talked the closer they grew. It was plainly obvious that the two really liked each other. So, one day, Clover took the next step in their relationship.
Clover: Hey, umm, we've been talking for a while now and I've begun to really like you...so, would you be willing to go on a date with me?
Qrow stared at the message on his phone, his heart racing. It took a lot of will power to gather the courage to reply to the guy he has a major crush on.
Qrow: Sure, I'd love to. When and where?
Clover: How about this Saturday, 7:00pm at this diner my roommate's parents own?
Qrow: Sounds good to me.
Clover: Do you want to meet there or should I pick you up?
Qrow: I think we should meet each other there. No offense, but I think it'll be safer that way considering you're someone I met online. You can never be too safe when it comes to online dates.
Clover: Yeah, that's completely understandable. My roommate's a cop, so she probably would've told me the same thing. I'll message you the address of the diner.
Clover gives Qrow the address to the diner owned by Robyn's parents.
Qrow: Thanks. I'll see you there.
Clover: Can't wait. 😁😉
When Saturday came, Clover was a little nervous as he was getting ready for his date with Qrow. He hadn't been on a date in years...he'd been to focused on taking care of himself and his mental health to date anyone.
"Hey, Robyn, how do I look?" Clover asked.
"Great, dude. Now, remember, if the guy turns out to be a creep and gives you any trouble...just kick him in the n*ts." Robyn told him.
Meanwhile in Qrow's apartment, he was on video chat with his nieces as he was getting ready. He had the camera tuned away while he was getting dressed.
"Uncle Qrow, we're so proud of you for putting yourself out there." Ruby said.
"Yeah, I told you that you were irresistible." Yang said.
"Now come on, let us see what you're gonna wear!" Ruby said, unable to contain her excitement.
Turning the camera towards himself, Qrow shows his nieces the outfit he was going to wear on his date.
"Hmmm...lose the tie." Yang told him.
Qrow takes off the tie.
"Unbutton the top three buttons and roll up the sleeves." Yang demanded.
Qrow does as told.
"Now, put on the necklace I got you for Christmas!" Ruby suggested.
"And muss up your hair a bit!" added Yang.
"Okay, there. Now how do I look?" Qrow said after doing what they suggested.
"You look great!" Yang and Ruby said with a thumbs up.
"Thanks for the help, girls." Qrow replied.
"No problem, Uncle Qrow." Ruby said sweetly.
"I so can't wait to tell Nora about this." Yang said clapping her hands excitedly.
Yang and Ruby wish their uncle luck on his date then end the video call. Qrow arrives at the diner and sees Clover standing outside waiting for him.
"Hi." Qrow greeted shyly.
"Hey, you look nice." Clover replied, blushing.
"So do you." Qrow said, blushing as well.
Clover holds out his hand for Qrow to take, of which he accepts. The two walk into the diner holding hands.