You're your own best boy! (raggedy andy x ftm reader oneshots)

Hoping he says yes

Authors note; apologies for slow updates 😓 I forget I write fanfic sometimes since I don't really use Wattpad. Anyways this is just more of a male reader x raggedy Andy :] no triggers or warnings !! Just fluff. Sorry if this type of date isn't your ideal either ! Remember that I take suggestions/requests.

Andy paced back and forth, feeling his cheeks grow warmer and warmer at the thoughts that swarmed in his head. He found himself going nuts, thinking of the perfect date and perfect way to ask a certain someone out. "I dunno Ann, what if he says no? I ain't ever been on a date before and I sure as heck ain't ever planned one! Like what do you even do on a date? Ya just talk n' hold hands or something?" Andy went on and on, questioning what dates were even about. He felt so pressured and stress and it felt like it was building up. Andy was strong and confident, even with you. But at the thought of affection and love and romance, he melts and dies down inside, like he can't take it. He didn't hate it, he just had never felt it before and didn't know how to deal with these new emotions.

"Oh Andy, you're stressing yourself. Don't worry too hard about it, I'm sure he'll say yes! You n' (y/n) have been so close, I just know he likes you back." Ann patted Andy on the back and smiled warmly at her brother. "I can help you set up the date too! Though I myself have never been on one, it can't be that hard? Especially if everyone else helps out too!" Ann closed her eyes and grinned. Andy felt some of his worry and anxiety wash away with the help of his sister.

Andy smiled brightly towards his sister, always thankful for her presence and constant kindness. Usually Andy is the one to calm her down and comfort her, holding her back from a breakdown or stress. It was good to know that Raggedy Ann could do the same for him when the roles were switched. All the other toys were trying to set things up, make the setting of the playroom be nice enough and clean. Some toys and stuffies came towards raggedy Andy and helped him clean himself up, checking him for lint, tears, stains, or loose stitching.

"A tie? Don't cha think a tie is too much, Ann?" Raggedy Andy questioned as Raggedy Ann straighted up and fixed a tie she had made for him to wear. The tie wasn't made of any sort of fabric, but rather paper. It was much like a paper flower she had made for him before to comfort him. "Well, you want to look your best don't you? Not that you don't always look good Andy! But you know I always see in shows that when a person wants to look good or their best they might wear something like this. Especially on a date or when asking someone out. Besides, I think it looks great on you!"

While all of this went on, you watched it all happen. Of course, there wasn't really anywhere else you could go other than be in the playroom. Whenever there were surprises like this and they had to be hid from someone, it was difficult. You weren't really blind to Andy's emotions either. He treated you a lot like a friend, but there was always an off tone in his voice. An odd way of speaking. An odd desire to always stare at you when he thought you couldn't notice. He was oblivious to the fact that he showed these emotions, ESPECIALLY in front of you. Andy had even let a few pet names slip out when referring to you, and when you asked what that was about he got all tuff about it and said "Mm what do ya mean? I call everyone that, I swear it!" Andy was so childish around you. When he got real nervous and felt himself in a trance around you, he'd turn so red and unbelievably nervous. He'd pretend to be all sorts of strong but fail extremely hard. Andy was always trying to show off for you too.

You smiled as you chuckled to yourself. "mm. He's so stupidly oblivious.." you muttered to yourself, recalling several times where Andy ended up acting a fool all because of his crush on you. That's when you felt a sudden wind and brush at your shoulder. Quickly, you turned around and was met by Andy. Andy wore a paper tie, which you thought was weird but in a good way. It was different, and didn't look half bad on him. Wasn't necessarily his style to look all fancy though. "Hey (Y/N). Sure is a nice day isn't it?" You shrugged your shoulders. "guess so. Nice tie, Andy. What's the occasion?" You both began to walk along a shelf that was by the window. "Well ya know I just wanted to look nice today! Do I need a reason to wear a tie?" You narrowed your button eyes but smiled. "Mm, no I suppose not. But I know you well enough to know it's not your style, and you never wear ties. Besides Andy, you look good everyday."

Andy perked up and though he was a rag doll, you could've sworn you saw his cheeks get more red and rosy. "Gee ya think so? I think the same of you ya know! I mean I think you look even better than me and greater and nicer as everyday goes!" Despite knowing about his feelings for you, you're never able to get over his compliments. They made you feel so warm inside and comfortable. You chuckled and thanked him. "I'm not sure about that one though, Andy. I don't think I could be more handsome than you are." Andy came to a halt and you both stopped. "What are you talkin' about?" He sounded confused and quite upset. You meant it as a compliment to him, but he saw it as if maybe you didn't find yourself handsome or pretty at all. "What?" You questioned, stumped from the gingers upset tone. "(Y/N) I think you're the most handsome good looking doll there could be! In fact I came here to talk to you because I...Well, I wanted to ask you out."

"Ya know we've been best buds for a while, n' I've only been realising that the feelings I have aren't just because we're friends. I like looking at you. I like the way you look. I like the way you talk n I like the way you act, n I just like everything about you. You're just so different, you're so understanding. One of the best guys I've ever met. So I was wondering..." He trailed off. Andy was able to say all that and confess so much but couldn't utter the words 'would you like to go on a date with me?'. It was adorable. As you saw him struggle to say the words, you grabbed his hand as best as you could and held it tight. "Yes Andy, I'd like to go out on a date with you."

Andy's eyes widened and he smiled from ear to ear, well, if he had any and if he could. He started move around in happiness and excitement, because wow, he couldn't believe he did it. And he couldn't believe you said yes. "So, let's get to that date everyone has planned for us." Andy instantly stopped and held his hands up. "Hey wait a minute...you knew!?" You shook your head and laughed. "There's no good way to keep a secret in the playroom you know. Besides, your emotions and feelings towards me was quite obvious." Andy felt somewhat embarrassed and dumb, because he had no idea you could see right through him. "Well that's not fair, I was trying to surprise you!" You shook your head. "Oh Andy it's alright, I'm surprised enough. I didn't think you would actually do it and have the guts to ask me out." You teased him lightly, nudging him with your shoulder before beginning to walk ahead. "What do you mean by that?! You sayin I'm not tough, (Y/N)? I'll show you! C'mon tuff guy let's just see!"

Andy jogged to catch up and nudged you back, and the playful bickering and teasing went back and forth. In the end; Andy was just happy you had said yes.

A/N: I legit didn't know how to end this LOL I randomly remembered that I had Wattpad and was like "oh yeah. That Raggedy Andy x male reader oneshot book-" and this unfinished oneshot was in the drafts so I tried my best to finish it for fun. I'll TRY to be more active but I don't really have many ideas. Sorry if this was less of a x male reader and more of a gender neutral!! Btw it mentions "handsome" and "pretty" because ya I think both terms can be used ! Guys can be pretty and handsome <3 anyways happy Valentine's day. I probably should've done a Valentine's oneshot instead but. Oh well- also ignore the fact that I'm posting this at 2 am on a school night. Also sorry if this is similar to the other two I wrote and like I didn't proof read this so apologies if it's bad !