Henry had waited all week for Friday night, he went out with his savings money and bought a new pair of dark blue jeans, red button up shirt and a small box that held a gift for you. Ever since you arrived to Derry Henry never knew how to admit his feelings for you so he just didn't bully or bother you, his friends were cool with you, well except Patrick, he didn't know what his problem was but he was gonna have to put him in check. Henry walked home and sped towards his room where he tossed the shopping bag down onto his messy bed, his dark red covers partially falling off his bed, his playboy porno magazines sat on his desk, some faded necklaces sat upon his dresser as well as some bruising medication. Henry quickly removed his clothes and walked towards his bathroom and took a quick shower and got ready. The blond male got dressed quickly and swiftly, he heard the front door slam and his stomach dropped as he was putting on cologne, the blond quickly shoved your gift in his pocket. "Henry! Where are you boy?" His father shouted, Henry took a shaky breath before stepping out of his room. "Here dad.. I was just leavin' anyway." Henry made a break for the door when his dad grabbed him by the bicep harshly and threw him back. "Now where the fuck do you think your going all dressed up boy?" Butch sneered staring at his son with disgust. "I'm just going out with the guys." Henry spoke trying to breath, his father gave a disgruntled grunt and stepped aside. "Do whatever the fuck you want, but if I get a call sayin' you were doin' somethin you shouldn't have I'm gonna beat your ass you hear me boy?" Butch snapped pointing a finger at his son aggressively.
Henry grabbed his car keys and walked outside to his 1983 Ford Bronco and started driving towards your house, but before he continued he stopped in town and grabbed (Favorite Flowers) for you. He continued his drive towards your house his wrist resting on the steering wheel while his fingers tapped the dash. Meanwhile you were rushing around your room trying to find something to wear. Your sister sat on your bed whilst you figured out what you would wear. "Y/N I'm sure whatever you wear Henry will like, your beautiful already. Just pick something." (Sisters Name) groaned. "(Sisters Name) that's the problem! I dont know what we're doing, am I supposed to wear pants or a dress? I want to look nice, you know how mum and daddy feel about appearances. I got it!" You gasped before you ran into your closet and grabbed out a short red floral dress, white ankle socks and white nike air force 1's your sister put your hair back into a braided half up half down style. You heard the doorbell ring and quickly put on your favorite perfume, some mascara, eyeliner and grabbed your black sunglasses before jogging out of your room with your sister close behind.
You saw Dallas and Henry standing next to each other at the door, Henry holding (Favorite Flowers) Dallas gave him a side eye, he was always a bit protective over you and after (Sisters Name) told him that Henry Bowers asked you on a date AND you accepted he wasn't too happy. "Hi Henry!" You smiled walking down the stairs. "You look just.. Wow.. oh! I got you these." Henry handed you the bouquet of flowers and you smiled before smelling them. "Thank you Henry." You placed the flowers on the entry table, you heard someone walk into the foyer and turned to see your father. "Good evening my darling daughter, I heard your going on a date tonight, is this him?" Your father asked looking you and Henry up and down. "Yes sir, I'm Henry Bowers." Henry stuck his hand out to shake your fathers. "Bowers.. Bowers... where have I heard that name...Ah yes! Your the sheriff's son! Well, I hope you two have fun, Y/N you dont have a curfew seeing as your with someone I can trust." Your father pat Henry on the shoulder before he opened the door for you and him. You started walking out the door with Henry when you arrived at the bronco he opened the door and waited for you to get inside and get comfortable.
You watched Henry rub his hands together before getting into the driver's seat and start the bronco with a loud roar of the engine. "So, where do you fancy for dinner?" You asked, Henry adjusted the bandana on his wrist as well as his leather cuff bracelet. "We could go to that new 50's Diner in town, whats it called.." Henry thought for a moment before tapping his fingers on the dash like before. "Dales?" You asked, adjusting your dress. "Yea that one." Henry looked to you before back at the road. "Sure, I haven't tried it yet so lets go." You smiled before Henry sped up and drove to town, he turned on the radio which started playing Wango Tango. You thought the song was nice so you turned up the volume. Henry smiled at you and started singing the lyrics. "My baby she can scream and shout! My baby she can move it out, My baby she can take a chance, My baby got a brand new dance. Wango Tango! Wango Tango!" Henry shouted over the music, you laughed to yourself, you had never seen Henry like this, maybe it was because he was just with you instead of in front of his dad, or his friends, or in front of the "losers club." he felt great. Once in town Henry turned down the volume and parked a bit down the block from the diner, he got out and when you went to open the door Henry jogged over and opened it for you, he also held out a hand for you to grab and to step onto the curb. "Thank you Henry." You smiled, you and him walked down the block and entered the diner. You chose a curved booth in the back, you sat next to Henry as he softened his composure, he seemed still so tense... "Henry? Whats wrong?" You asked placing a hand on his, he jumped, you gave a sad look which he seemed to notice.
"Nothing I'm fine, what's bothering you? You look like you just saw a kicked animal." The blond gave a small nudge to your side, you looked into his blue eyes, in this light they looked almost pastel blue. He cocked his head to the side and just stared at you. "Hi welcome to Dales, what can I get started for you two love-birds?" The waitress smiled winking at you, Henry sat up straight and looked to you. "Two waters a coke and..." Henry continued looking to you. "(Favorite Drink) please." You looked at the waitress and smiled, once you and Henry got your drinks you spent a bit talking about things, like what you did that week leading up to that moment. Henry stared at you as you talked about the painting you finished the day prior, he liked seeing you talk about something that made you happy. You stared at the menu the waitress handed you as she placed down your drinks, Henry started flipping through and bit his cheek. "Thanks. Everything sounds so good, what are you in the mood for?" He asked, placing it down, you thought for a moment before placing it down with a smile. "Yup I'm gonna get (Favorite Food)." You intertwined your fingers together and rested your chin a-top your hands. "Ooh, good choice pretty girl." Henry smirked mimicking your position. "Oh shush Bowers." You giggled, you heard a bunch of laughing before you turned to look at the entrance. "Shit.." You froze, Henry noticed your behavior and looked towards the door and saw your friends. "Oh.. I can step outside if-" "No, its okay, stay here with me." You said firmly, Henry nodded and sat back in the booth.
Richie and Ben were the first to pass by and saw you with Henry. "Y/N? What the fuck are you doing here? Especially with him!" Richie said in a bit of a louder tone, now he was starting to draw attention to you and Henry. "Richie listen-" "Shut the fuck up Bowers. I'm talking to her." "Richie!" You gasped, Ben just stared at you he knew and believed you should have a life of your own, but to go on a date with the guy who carved his initial into his stomach? Why? The rest of the gang showed up and looked at you with disappointment, Beverly motioned for you to come with her. You stood up and went with her. "Listen as much as I don't like Bowers you deserve to have some fun, but please, be careful Hockstetter has been acting really shady and I tell you this from one friend to another. Watch your back around Patrick. Now, go have fun on your date, I'll handle the guys. And you better tell me what happened I need to know." Beverly hugged you tightly and you returned it. "Of course, thank you so much Bev..I'll tell you everything that happened tonight." You smiled before going back to the table, Beverly rushed the boys out the door disregarding their protests of anger and rebellion. Once they were gone you sighed and rubbed your temples out of embarrassment. Henry sat silently before placing a hand on your shoulder. "Listen I'm really sorry." He spoke sincerely, you chuckled before sitting up. "Don't be, Richie decided he wanted to act like that." Your food came out, and as the waitress placed your food on the table Henry gave you what you could imagine was an attempt at a hug? You smiled and hugged him back.
After you finished your food and Henry finished his the waitress placed the bill down on the table. You made break for the bill but Henry beat you to it. "Nice try, just because your rich doesn't mean I can't pay for dinner." You gasped. "I never thought that!" You defended crossing your arms. Henry chuckled and payed for the meal. Henry got up and put his hand out for you once back at the Bronco Henry started driving towards the fields. Once there he opened up the back panel, and fixed something, you got out of the front and walked to the back where he had a small radio set up, pillows and blankets as well as a small velvet blue box. "Oh Henry this is amazing, what's this?" You picked up the small box and turned to him, he took your hands in his own and opened the box, you looked and saw a beautiful simple gold chain with a small sun pendant in the middle. You smiled and removed it from the box. "Henry its beautiful." You felt bad because you didn't have anything to give in return. "I've been waiting for four years since I saw you in fifth grade to give you this, may I?" He asked you handed him the necklace and he put it on as you moved your hair. You smiled and placed a hand on it to feel it resting between your collar bones. You smiled and sat on the tailgate of the Bronco whilst Henry turned on the radio, you two sat and talked for what felt like hours...
The next morning you felt yourself laying on-top of something.. or someone. You saw a red shirt, a gasp emitted from your lips as Henry awoke quickly. "Shit! Were we out here the entire night?!" You pleaded praying you wouldn't be in trouble when you got home, you quickly covered your mouth.. you had never sworn before. Henry merely started dying laughing at you as even he had never heard you swear before. "Did the towns princess just say a swear word?!" Henry said dramatically gasping as you climbed into the front seat while Henry closed up the back. "Shush Henry this is serious!" You rubbed your eyes trying to wake up as fast as possible. He sped down the road towards your home and when he passed through the front gate you saw Dallas on the front porch, lit cigarette with two of his closest friends. "No No No what are they doing here?" You mumbled, the blond noticed your discomfort and pulled to a stop. "Where were you two last night hm?" Dallas questioned, his green eyes narrowed at Henry. "Dallas we fell asleep in the back it's not that big of a deal.." You spoke softly getting out of the car, Henry got out as well and walked you to the front door. "I'll see you around Henry, I had a bunch of fun last night." You spoke softly leaning forwards to kiss him on the cheek. "Y-Yeah I'll see you around princess." He smiled before jogging off towards his car and heading off.