For those of you who have read Intoxicating Desires | T. Al Ghul, you will know that I have included the Wayne boys in this story too and as always, Richard takes the spotlight.

So one day I was just thinking that this version of Richard is supposed to be even more social and well-liked in Gotham's society than Bruce. And I felt that the Richard from this story has probably played both wingman and matchmaker for Bruce multiple times (and yes that's without Bruce's permission).

I posted it on my message board and a comment by penguinflops34 inspired me to write this one shot where Richard attempts to find a compatible love interest for his adoptive father. Therefore, in this one shot, we're going to be looking at five times Richard set Bruce up with someone and one time he found him a very special someone (you're free to imagine who that is).

I will be referring to the dates Richard has set up as Cupid's Arrow and the number beside the title refers to the order. Also, I am taking a lot of liberty with the origin stories of these characters who are canon to some extent (not my fault they were shown so little), under the one statement that this is an AU story so a lot of the stuff is different (please ignore if anything seems incorrect from canon, let it slide).

So without further ado, let the fun begin. 

~•~

Cupid's Arrow 1: Julie Madison

Richard remembered the first time he had seen Julie Madison in a theater play at the Gotham Auditorium. He had been recently adopted by Bruce Wayne and it was one of those nights that Alfred had suggested they should all go out on a family outing.

And given Alfred's preference for literature and drama as a quality source of entertainment, they ended up at the theater. Richard was new to that wholly different life as an adopted son of a wealthy businessman and he was still adapting to it. While Bruce was adapting to the prospect of having a child to look after.

Not exactly a child since he had hit his teenage years by then but still a very different situation than what Bruce was accustomed to.

Julie Madison was also a rising star back then, starting her career in theater and then going big on the silver screen. A couple of her movies had come out and some of them were a success but she still performed in theater plays held in her native city.

Richard remembered the autograph signing after the show had ended and he had meekly gone up to her with his little autograph diary. He remembered getting her autograph and asking her when her next movie was coming out. 

After that, he didn't meet her until he attended the first society event he was allowed to after turning fifteen.

"Aren't you the Wayne boy? Sorry, I forgot your name again," she had asked as she was signing the autograph diary a second time.

"Richard Grayson," he told her, that once not so shy around her as he had been earlier, "oh and do you know, you are the first autograph on this diary too."

"Wait, no..." She looked both surprised and delighted as she turned back the pages to find that autograph from a few years back, "that is so sweet."

"I really admire your work," he resumed effortlessly with a bright smile playing upon his lips, "especially that rendition of Little House On The Prairie."

"That was so long ago, dear, I thought no one would remember seeing it," she was both awed and touched by his genuine compliments.

And of course, it did not take long for Richard to get rather friendly with her, talking about their lives and unknown to her, Richard was on an agenda.

"So you know my Dad, I mean guardian, yeah him," he tilted his head very slightly in Bruce's direction and the woman nodded, listening to him eagerly. "Well, he's a fan too in fact he introduced me to your work. But he's shy and I feel like I should do him a favor."

"Oh," the smile playing upon her lips widened slightly, "I didn't think he would be shy."

"Miss Madison, you know what they say, take the rumors with a pinch of salt," he added and it made her laugh.

"You sure are something, Richard, I am so glad we met again."

"Likewise," he tore off a page from his diary, pushing it towards her with his pen, "so mind if I ask for an autograph on his behalf? He would ring you up and thank you for it himself."

A bright red tainted her cheeks though Richard could put it down as either a blush rising to her cheeks or an indicator that she had had too much to drink. But it worked in his favor as she scribbled her number on the page and gave it back to him.

With his task being done, he waited for the right opportunity to slip away and tell Bruce of the newly set weekend plan he now had on his schedule.

Bruce was talking to a group of men around his own age and older when Richard approached.

"Bruce, a word?" He smiled politely at the other guests but tugged at his sleeve to let him know that he had to talk to him urgently.

Bruce excused himself from the group and took him aside, "yes?"

"She doesn't have a boyfriend currently, she likes to go out on dates to the beach and her favorite restaurant is that French outlet we went to last time we were in Robinson. Also, reservations are open for this weekend. You're welcome."

He stared at him in confusion, "what was all that?"

Richard rolled his eyes dramatically, "Miss Madison, I booked her for you on a date. You're welcome."

He looked rather startled, "no I heard you the first time but who asked you to? And wait... A date? Dick, you've got to be kidding me..."

The boy raised an eyebrow at him, "did I kid you when I said I would help you out?"

"Who said I needed help? Just because I said she's a good actress doesn't mean I am interested in her personally." He spoke up, making sure not to make it seem like they were having a disagreement because they were technically still at an event and the paparazzi could churn out a whole story out of it.

"Yeah, I hear you. I also know that you are terrible at asking ladies out," the boy stated in a rather matter-of-fact tone, "you're letting one ancient relationship govern your future choices and I can't be a party to that, sorry. Also, that is why you have fifty articles on you being a playboy and not a single one on you being in a serious relationship. Pitiful."

Bruce did not know whether he should be alarmed at the fact that Richard had been tracking the number of articles written about him as well as their contents or that he was going to be the reason for that one article of Bruce Wayne seriously dating someone.

He hadn't considered being in a serious relationship ever since Andrea Beaumont. And Richard calling her ancient reminded him that it really had been a long time since then and perhaps he needed to stop judging every woman based on that.

"We are not having this conversation here," he warned, knowing full well that the people around them could hear them even if they talked in low tones.

It was embarrassing for him, to say the least.

But Richard was not going to give in to his excuses. "Fine, then take the very lovely Miss Madison out on a date this weekend and we will have this conversation after. Adios, Au Revoir, La Revedere. Oh and best of luck."

Lifting his imaginary hat, the boy had vanished, leaving Bruce to deal with one more situation that he initially did not want to get stuck in.

But then abruptly Richard had popped back like a genie out of a magic lamp, "I almost forgot, the page I slipped in your pocket while you were talking to those gentlemen? It has her number so..."

Bruce interjected as he knew very well what Richard would add if not stopped right then, "I am not going to say thanks."

He smiled nevertheless, a playful spark glimmering in his sky-blue eyes, "but still, you're very welcome."

***

Cupid's Arrow 2: Chase Meridian

Bruce had no idea he would regret sending a young and exuberant Richard Grayson to the training camp held by the GCPD. He thought it would be good for him but instead, he got swept into another of Richard's attempts at playing matchmaker though it was a good six months after his relationship with Julie Madison fell to shambles.

Turned out that the psychoanalyst who worked at the police department, Chase Meridian, became a test subject for Richard to try the cupid's arrow on for the second time. But it backfired and became a rather messy situation both for Bruce and Batman.

"Can you set me up with Batman?" The woman asked, twirling the olive in her martini aimlessly, "he's way more interesting than Bruce Wayne."

"Um about that... Batman has a whole city to save, I don't think he will be interested in having a love life," Richard replied, just then realizing that his efforts in trying to help Bruce out with his love life were also going in the exact opposite route of that statement.

"But he's so heroic and mysterious and hot and I would love to study his profile," she remarked, tilting her head to look at the boy who seemed slightly uncomfortable, "I mean both the mental and the physical one..."

"Too much info," he grimaced, "but sorry, I don't have contacts that could reach up to Batman."

"Oh but Bruce Wayne would know him!" She seemed to have been struck by a Eureka moment, "I remember how the press is so sure of him being a very close friend of Batman. Why don't you set me up with Bruce first and I will figure my way out from there?"

"Miss Chase, I am sorry, that's not what I had in mind. I can not let you break his heart when you eventually pick Batman over him."

Her hand gently patted his shoulder but it seemed more that she was feeling sorry for him, "my dear, you shouldn't feel awful about that. You are great at what you do really but I feel I should pursue this one on my own."

"What I do?" He paused, looking at her in alarm, "what do you think I was doing?"

"Putting in a good word for your Dad, honey, I am a psychoanalyst, I see behavior and I decode it simple as that," she stated off-handedly as if it was the most simple thing in the world, "you truly are a sweetheart for trying to help your Dad find his future wife but I am not interested. Though I am interested if he is willing to share Batman's whereabouts. Oh and I wouldn't mind a threesome."

"You know if you call him my Dad one more time and mention things like that so bluntly, we're gonna have a problem," he was slightly tight-lipped, "because he might be a great Dad and all but he has no idea I am trying to set him up with someone and I would prefer to keep him unaware about it now."

"You do you, honey, forget I said anything," she brushed his remark off breezily but then straightened, just realizing something, "so would you do something for me in return?"

"Nope," the reply was very immediate.

"Hear me out, come on."

He knew he would regret that had to give in, "okay, what do you want me to do? I will still say no, just so you're aware."

"Why don't you help me set up a rescue date with Batman?" Her eyes had lit up and Richard felt both awkward and alarmed at the same time.

He was starting to realize that not all his picks for Bruce were going to be as easy to handle and conventional as Julie Madison had been. Right then he had just picked the wrong person and was stuck.

If something wasn't done about it soon, Bruce or rather Batman would be stuck too.

"I am not even going to ask you to elaborate-"

"Oh, but I had the perfect place in mind and the perfect setting and Richard, darling, you have got to hear this."

Richard knew he had to escape and there was no excuse he could think of at the moment. So he just pretended to have spotted Alfred and bolted out of his chair, "oh no, Alfred fell down the stairs! I have to go."

Needless to say, the next few weeks were torture for Batman as Chase was actually chasing him and he could do nothing about it. And when he found out it was all due to Richard's matchmaker game gone wrong, he couldn't have gotten angrier at the boy.

The only problem was that being angry at Richard and actually facing him when angry were two different things entirely.

Of course, he was angry that Richard got him into trouble but the anger was futile when it came to confronting the boy because over time, he had gotten fond of him too and couldn't bring himself to rebuke him.

Though it did not work in his favor and resulted in Richard taking a lot of liberties with him.

Such as still having the nerve to try and set him up with a journalist the next time. Frankly, Bruce had no idea when his ward's matchmaking efforts would come to an end and when he would finally be free of going along with it just because Richard created a situation he couldn't back out of.

***

I have broken this up into parts due to time constraints that have limited my writing for now. See you all soon with the remaining parts and you guys are free to guess the other Cupid Arrows. They are all canon characters so there's a fair chance you will get the guesses right.

And I hope you guys enjoyed this because I truly had a lot of fun writing it. There's much more to come in the upcoming chapters so stay tuned.

~•~