Henry meets Betty when doing some accountant work for her floor. He asks her if she would like to go out for lunch sometime, Betty refuses because she knows this will upset Walter, so she makes a excuse saying she's too busy. The next day he asks her again. So, seeing no harm in it, she says yes this time. They go to a Japanese restaurant where they serve sushi. Walter walks in on them having a good time, and suspects the worse. When Betty tells his otherwise, he still suspects the worse and gets angry and storms out. ("The Lyin', the Watch and the Wardrobe")
Betty is at her desk working on an expense report for Daniel when Henry comes by and asks her if she's making her Christmas list. He spots mistletoe on her desk. She says it’s just holly, but he kisses her anyway and tells her she's the girl he's been looking for. But it looks like this was all a fantasy as Betty wakes up in a shock from this dream and glares at the photo of Walter by her bed before throwing the sheets over her face. Betty reluctantly accepts the offer. A bundle of fake snow arrives and Betty walks it into Henry, spilling it all over both of them. He tries to pull some out of her hair but feel bashful. He then makes a series of unintentional double entendres while Betty tries to hide her excitement when he tells her that he will be 'on top of her' for the next few days overseeing the party budget. Later that same episode, he gives her a snowglobe. ("Fake Plastic Snow")
Henry, who hails from Tucson, Arizona, is a bit of a bookworm with an excellent memory for facts and figures. He often sprinkles such facts in his conversations with Betty, followed by the statement "It's just something I know." Betty and Henry appear to mutually share an attraction, and they seem to be heading towards a relationship. However, Betty abruptly leaves the Christmas party after misunderstanding a situation where a model forces a kiss on Henry. This drives Betty back to her ex-boyfriend, Walter. When Henry calls after the party, he was intercepted by Betty's sister, Hilda. Knowing his attraction to Betty will doom her relationship with Walter, Hilda "loses" Henry's message.
As the first half of season one ends, Betty finds herself in a romantic dilemma: She still has feelings for Henry even as she tries to work things out with Walter. Betty continues to avoid Henry, but learns Henry's "kiss" with the model was not his fault. During the episode "I'm Coming Out," Betty is busy with organizing Fashion Week for MODE and she re-encounters Henry for the first time since the Christmas party. After Hilda further interferes with them conversing, Henry eventually asks Betty why she never returned his call. She discovers Henry called to see Rudolph the Red-Nosed Reindeer and Hilda purposely "lost" the message.
Henry asks Betty on a date to see the musical Wicked, but Betty affirms "just as friends." That night, Walter tells Betty he accepted a management position in Maryland, and the two break up. At the same time, Henry was seen at Betty's desk at MODE with a gift, a Wicked shirt with a note that read: "Can't wait, green girl!" But, the following morning, Henry confessed to Betty he had a surprise visit from his ex-girlfriend from Tucson, Charlie, who wanted to reconcile their relationship, not knowing Betty and Walter had broken up. He gave her the Wicked tickets, apologizing, and left Betty broken-hearted. ("Brothers")
Henry is surprised when he finds Betty and his now official girlfriend, Charlie, talking in the lunch room. He later thanks Betty for inviting Charlie to a party and he's confident Betty does not feel anything for him; that is until Betty calls him over to a downtown subway station and finds out she lost track of Charlie intentionally. He then questions Betty as to why she did it and finds out her true feelings for him. Just at the moment when Henry and Betty were about to kiss, Charlie appears back with a smile on her face saying: "It was fate that separated us Betty" and also states she will stay in NY indefinitely. ("Derailed")
A semi-conscious Henry told Betty he loved her. In the following episode, A Tree Grows in Guadalajara Betty believes she sees Henry in Mexico. She follows the apparition and discovers her grandmother's house. Her grandmother, mistaking Betty for her mother Rosa, encourages her to fight for her love. Betty resolves to fight for Henry. (" Secretaries' Day")
Charlie declares she is pregnant, and Henry opts to go with her to Tucson after a long, tearful goodbye with Betty. However, Charlie had been cheating on him with Dr. Farkas for 2 months, and therefore the baby could possibly not be his. ("East Side Story")
Henry gets off a bus in New York City. He tells Betty (in the following episode he has returned to Meade because he needs the benefits for his child-to-be and that there were no job offers in Tucson. However, in "Family/Affair", Christina tells him the truth about Charlie's infidelity. Henry shows up at Betty's house intoxicated from wine coolers and declaring his love for her. Betty is hesitant to resume her romance with him, and they agree to wait. Henry, after some time, finally calls Charlie and she confesses everything. They agree he should take a paternity test. ("How Betty Got Her Grieve Back")
Christina tells him the truth about Charlie's infidelity. Henry shows up at Betty's house intoxicated from wine coolers and declaring his love for her. Betty is hesitant to resume her romance with him, and they agree to wait. Henry, after some time, finally calls Charlie and she confesses everything. They agree he should take a paternity test. ("Family/Affair")
Henry shows up to Betty's house, drunk. He tells her that he loves her and she is beautiful in a sort of drunken way. She then takes him upstairs and puts him into bed. The next morning, He meets Hilda downstairs and they have breakfast together. Henry has to face his ex-girlfriend Charlie after finding shocking news about her pregnancy. ("Betty's Wait Problem")
Henry, as Betty's request, tutors a grieving Justin in Algebra. Justin's self-admitted "bad-ass" behavior, and Henry's inability to manage him, agitate Henry greatly. Confused, Betty asks him why; he responds it is because he is about to be a father and revealing he is the father of Charlie's baby. Betty asks him to leave, and any hope for their relationship reaches a screeching halt. Betty attempts to land a date with an online suitor and trying to avoid Henry completely. The date, however, goes sour and Henry, conveniently spying on Betty's date, cheers her up and takes her out to dinner. The dinner is awkward to say the least and two are mistaken for a couple preparing for an engagement! A woman from another table cries out, "He's proposing!". This is the last straw Betty can stand and she promptly leaves the restaurant, running home. ("A League of Their Own")
Betty's family is concerned for her loneliness, Christina is unaware, and Daniel threatened to fire Henry. Betty, using her usual "good judgment", decides to keep their romance a secret. Inconspicuously, Henry and Betty continue to date and go to a showing of the Broadway hit, Wicked because they couldn't the year before. However, Daniel and Gio give the pair a hard time and their date is an utter disaster; from a fight in the lobby via illicit text messages to actually stopping a live performance. As Betty continues to feel like her heart is in the wrong place by lying to everyone she cares about, she decides to call the night off. Henry is upset about keeping their relationship a secret and explains Betty won’t be the only one getting their heart broken.Their first date was a nightmare and Betty returns to her home, crying on Hilda’s shoulder. However, after Hilda gives her some sisterly advice, Betty knocks on Henry’s apartment door and the pair reconcile. ("Something Wicked This Way Comes")
Betty's father discovers she has been sneaking into Henry's apartment in secret and after a family fight, she leaves. Planning to move out, Henry tells her she can move in with him and the two start living together, immediately discouraged as they realize in a matter of months Henry will have to move back to father his child. Henry convinces Betty to reconcile with her father, as Ignacio will still be there for Betty after Henry leaves. ("It's a Nice Day for a Posh Wedding")
Following this, things between Betty and Henry seem to be going splendidly, with a flamboyant display of flirting between them occurring frequently. Henry pretends to be infatuated with the weekend receptionist, L'Amanda, in order for Betty to sneak into her office to obtain Bradford Meade's will. ("I See Me, I.C.U")
Things start to get shaky when Henry walks into the Suarez residence seeing Gio dancing with Betty, and apparently having a good time. Back at Henry's apartment, Betty tries to replicate Gio's description of how he would theoretically treat the "woman he loved" in the short time they had left together, and Henry only gets frustrated. He tries to go along with what Betty wants, which includes Betty attempting to eat ice cream off of Henry's stomach with scalding chocolate sauce, and Latin dancing. At the dance club Henry becomes very defensive with Gio trying to impress Betty and Hilda, Henry's sleeve catches on fire and he storms out. Later, he comes back while Betty tries to call him, and starts dancing out on the floor. Betty appreciates that Henry tried to make an effort, and they leave the club. However, in another episode, Henry's competitive side is brought up again, when he jealously challenges Gio to see how many phone numbers they can collect from women. He also tells Betty he is uncomfortable about her relationship with Gio, Betty responds by saying she'll stop seeing Gio. Although she continues to see him and lies about it to Henry, when he finds out, after an incident where he accidentally ended up punching Gio, he says she can be friends with whomever she wants and they seem to be still strong. However, when a heavily-pregnant Charlie shows up in New York, she constantly tries to interfere in their relationship and ruin their dates by pretending to be ill, coming home early and generally demanding Henry's presence. She later tells Betty it was because it was so difficult seeing the man she loved in love with someone else. The tension in Henry and Betty's relationship over his impending departure seemed to have been taken care of when Henry proposed that instead they stay "together forever", flying back and forth to each other. While Betty was initially thrilled by the idea, when she saw Henry holding his newborn son after Charlie goes into labor at a baby shower Betty had thrown to try and bond with her, she cries as she sees it as the end of the relationship after advice from Claire Meade and Ignacio. This does not prove to be the case when Henry comes back and pops the question to Betty, who already was asked by Gio to go to Rome.
Betty chose neither Henry nor Gio ending their relationship and refusing his proposal. However, Betty learned from his replacement at the accounting department he has a Facebook account revealing he now travels in South America with a new girlfriend named Samantha. Despite the surprise news, Betty does answers his invitation to join his Facebook list. ("The Manhattan Project")
Betty and Henry meet once again when Henry returns to New York for a few days with his new girlfriend. As Betty is talking to Matt over the phone, she sees Henry hailing a cab, which prompts her to drop the beverage she was holding. Then she continues to "Facebook stalk" him for the next couple of days. This is helped by Henry making constant updates of what he's doing in NYC and where he is doing it. One day, Betty ("encouraged" by Amanda and Marc) decides to visit the coffee place she thought Henry might still be in. Unexpectedly they bump into each other on the street. Here we meet his girlfriend, Chloe. Thanks to Amanda and Marc, Betty ends up making a double date with Henry and Chloe. During the date, at a baseball game, Matt sees his first sign of Betty still being attracted to Henry, but they talk it out afterward. However, after a terrible day at work, Betty ends up contacting Henry (who updates he's leaving NYC). Henry helps Betty through her tough time and they end up admitting to each other they still have feelings for one another. Henry even goes to say his many updates were attempt to lure her to him and she finally did, three days later. As they have a goodbye hug, Henry kisses Betty but both pull away, until Betty goes in for the kiss. As this happens, Matt shows up at the park they are at and witnesses Betty's cheating. Betty continues to feel guilty but, thanks to Hilda's advice, she doesn't tell Matt. ("Curveball")
Following a night out in London, Christina informs Betty that she had spent the night drunk-dialling her ex-boyfriends. Although Betty thinks nothing of it, the episode ends with Henry receiving the message that Betty had left him, inviting him to Hilda's upcoming wedding as her date. Henry arrives in New York in the next episode with his son, Nate. He informs Betty that he has a job interview for a major company, and would be moving to the city full-time if he gets the job. The pair share breakfast, but it becomes obvious that the spark is not entirely there anymore. Betty appears over him and loses her temper when Nate acts wild in the restaurant. When a patron criticizes her for not controlling him, she loses it saying "He's not my kid!". Henry may have feelings for her, but it becomes apparent that they have been away from each other too long to reunite. They have changed and want different things in their life. Despite interference from Daniel, Henry gets the job, and wishes Betty well, though does not attend Hilda's wedding. ("London Calling")