In November 2017, Gemma Winter attended a party and caught the attention of Henry by stealing an ornament and writing 'pie in a tin' onto a shopping list. Henry decided to speak to Gemma and was charmed by her quirks of stashing snacks in ovens and her references to pies.
Gemma pretended that her name was Jemima and led Henry to believe that she was a nurse. When the police arrived at the party, Gemma rushed out, believing that they were going to arrest her for stealing the ornament. Henry was upset not to have got Gemma's number but noticed that she had left her shoe behind and decided to seek her out in Weatherfield.
Henry called in to The Kabin and asked Norris Cole if he knew of anybody called Jemima who was really sweet, in their twenties and had a lovely laugh. Norris told Henry that Jemima was far too posh a name for Coronation Street and that he may have more luck in a different area of town.
Norris later realised who Henry was referring to and led him to the Rovers, where Gemma was speaking to Liz McDonald about her time at the party. Henry later suggested that they should meet up again and complimented Liz on a 'fantastic little boozer'. Recognising who he was, Liz informed Gemma that Henry was Cecil Newton's grandson and that she had landed on her feet with a relationship with him.
In January 2018, Henry was invited to Chesney Brown and Sinead Tinker's wedding. He expressed his hatred for weddings to Gemma, and constantly made snide remarks about the day. Pulling him to one side, Gemma explained that she wasn't impressed, and dumped him on the spot. Later, Henry tried to sweet-talk his way back into Gemma's good books, and she took him back. Henry then took a call from his friend Hugo, promising to win their bet.
After learning that it was Henry's birthday, Gemma managed to win a hotel break for two. After telling Henry about the arrangements, Henry made out that he had a meal with his family that day, and that she wouldn't enjoy it.
Disappointed over not spending the day with Henry, Gemma enlisted the help of Cathy Matthews, Brian Packham and Liz McDonald in making a Newton and Ridley themed surprise birthday party for him. When Henry arrived he was touched by Gemma's kindness, and seemed to enjoy spending time with Gemma and her friends. Henry took a call later on in the night, telling him to leave, but ultimately he decided to stay at the Rovers with Gemma.
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