Hiccup sighs "I have to make a shield to have an edge at defeating your daughter in combat."

Ingrid smiles "thank you son."

Hiccup leaves the stands and walks to the forge to work on making a custom shield.

(With Astrid)

Astrid fought against many teenagers who try to beat her in duels.

Two days later.

Hiccup finished the custom shield.

Gobber ask "what's different about that shield?"

Hiccup grins "you'll see in the arena."

He walked to the arena with Gobber to watch Astrid face Dogsbreath.

Astrid gave it her all and quickly defeated him.

Next was Thuggory.

Thuggory tried his best to beat Astrid, but she disarmed him and then knocked him out and scoffs "pig."

Snotlout walked pasted Hiccup and stood in the arena and says "Astrid? Why don't we quit this trial and let's get married because we both know you want to marry me."

Astrid scowls at him spinning her double bladed ax."

Gobber starts the match "begin."

Astrid charge at him hitting his club with anger until she disarmed him and kicked him in his stomach before hitting him over his head with the flat side of her ax.

Gobber sighs "Astrid wins again! Any more challengers?"

Hiccup walked with a shield and a bundle of flowers in the arena and says "I would like to challenge Astrid"

Astrid ask "what's the flowers for?"

Hiccup answers "happy birthday, Astrid."

Astrid takes the flowers from him and smell the scents and says "thank you, Hiccup" and hands them to Gobber to hold."

Gobber sighs "begin the match."

Astrid walked around wanting Hiccup to make the first move.

Hiccup smirks "is that all you got? I'll be sure to turn you into a wife and leave you thinking about wanting me."

Astrid scowls and charge with her ax and slammed it on Hiccup's shield to end up having it wedge tightly in his shield.

She tries to pull her ax out, but pulls the shield off too and tries to free her ax and scowls "what trickery is this?!"

Hiccup grins "I knew I couldn't beat you in a duel, but I'm sure I can beat you in hand to hand combat."

Astrid threw down her ax shield and charge at Hiccup in rage.

Hiccup tripped her leg making her fall face first and then pile on top to pin her for three seconds.

Astrid scowls "Hiccup!"

Gobber smacks the stone floor "PINNED!"

Hiccup gets up off of Astrid and grins proudly.

Astrid got up and punch him in his shoulder "jerk. If you win the second challenge, I'll make the engagement horrible for you so that you refuse to want to marry me."

Hiccup pauses at thinking she likes him.

Astrid left the arena and walked over to where her parents are sitting.

Ingrid scowls "if he wins your hand in marriage and you anything to break his heart again, you will be grounded from training with your ax!"

Astrid sighs "yes mom."

(Inside the arena)

Hiccup stood tall as the Monstrous Nightmare was released from his cage.

He watches as the Monstrous Nightmare flew around the arena with his flames going.

The Monstrous Nightmare fired shots out the chained fence.

He turns to the boy on the ground and hisses at him.

Hiccup gulps "I think he's too mad at me?"

The Monstrous Nightmare lands on the stone floor and approached Hiccup slowly with his teeth bare, growling at him.

Hiccup backs up while saying "I'm sorry, Nightmare. I didn't know it would take three days to prepare myself to face Astrid and you."

The Monstrous Nightmare snorts at his apology.

Hiccup lifts his palm up and turns his head to trust the Nightmare to not harm him.

The Monstrous Nightmare grabs his hand and sucks on it to make it cover in dragon spit.

Hiccup sighs "that stuff doesn't come off easy."

The Monstrous Nightmare chuckles at payback before touching his snout with Hiccup's palm.

Gobber yells "that's it! You survived the match!"

Hiccup looks at the villagers to find Astrid and smirks at her.

Astrid shakes her head "no. I won't marry you" And runs to the forest.

Hiccup left with his parents to go celebrate.

Night time came when Hiccup walked inside the forest to find Astrid.

He finds her hacking trees in anger and comments "I'm sure you killed a lot of trees in anger."

Astrid turns around and scowls "you won my hand in marriage, but your not going to have a happy marriage because I'll be anything but nice to you! Your not my type of boyfriend and your the worst Viking born here! You don't deserve to live! Save your apology! I don't want to hear anything you have to say!"

Hiccup stood there until she walked two steps and collapsed from exhaustion.

He carries her home and inside her bedroom to tuck her in.

Afterwards, he walks downstairs to see Ingrid sitting down at the kitchen table and says "she's going to be hateful towards you before she sees you for what your worth."

Hiccup sighs "I don't think I want to marry her after tonight, but if you insist on me marrying her, I will try to stand by her side."

Ingrid smiles "if she breaks your heart again, I threaten to ground her from training with her ax that you made her last year."

Hiccup leaves the Hofferson's house to go to bed.

As he lays in bed, he thinks about his future and ask "what would it take to win her love?"

In the morning, he eats breakfast and leaves the house to go walk to the arena.

Once he gets there, he frees the dragons from their cages and says "if your hungry follow me to catch breakfast for you all."

He climbs on Toothless and fly out of the arena over to the sea to catch fish.

The arena dragons follow running in opposite direction to run the fish into a trap of net.

When he returns with the arena dragons, he sees his father waiting for him.

He ask "what do you need, dad?"

Stoick answers "tonight, me and Magnus will be discussing your marriage contract with Astrid."