Lyndsey McElroy

Lyndsey McElroy
Vital statistics
Names	Lyndsay McElroy, Cinnamon
Gender	Female
Race	Human
Occupation	Actor
Origin	Two and a Half Men Season 7 Episode 19: Keith Moon Is Vomiting In His Grave, April 12, 2010
Alignment	Good
Age	44 (S12)
Created By	Mark Roberts, Don Foster, Eddie Gorodetsky, Jim Patterson
Height	168cm (5ft 6in)
Weight	52kg (115 lbs)

Lyndsey Ruth Anne McElroy is a prominent recurring character in "Two and a Half Men" since the seventh season. She is the mother of Eldridge McElroy, who is a close friend of Jake Harper, and is in a relationship with Alan.

She is portrayed Courtney Thorne-Smith

Appearance

Lyndsey McElroy is of average height, with fair hair and an attractive, slim figure that remains consistent throughout the series. While she ages slightly over the years, she manages to maintain her figure.

Personality

Lyndsey often exhibits a slightly masculine demeanor, particularly evident in her fondness for beer. She has a history of struggling with alcohol addiction, a fact that becomes clear when she vomits all over the interior of Walden's private jet after becoming extremely intoxicated

Despite her love and care for Alan, Lyndsey is known for her promiscuity and has had attractions to other men, including Walden, during their time together. This tendency is highlighted in the series finale, where she even visits a pawn shop to inquire about the value of the engagement ring Alan gave her. It's unlikely that she actually pawned it..

Biography

Background

During her high school years, Lyndsey was in dire need of money and ended up appearing in a low-budget pornography film titled "Cinnamon Buns." The film featured a scene at a bakery where she was covered in frosting. Herb Melnick, who discovered the film, fantasized about her being naked. Lyndsey later revealed this part of her past to Charlie and Alan.

Life With Alan

She first met Alan in the episode "Keith Moon Is Vomiting In His Grave," where she was introduced as Eldridge’s mother. Initially, Alan planned to tell Eldridge about her, but he was captivated by her beauty and instead took her out for a drink. They ended up having sex in a bathroom. From there, they began seeing each other regularly, and their relationship blossomed. To ensure they could spend private time together, Alan bought a hotel room for their dates. However, their plans were disrupted when Lyndsey experienced a period. Despite this, Alan showed patience and understanding, and they grew to deeply care for each other. They decided to keep their relationship a secret from their children.

Lyndsey later asked Alan to move in and after some hesitation, he agreed to move in with her. However, this decision caused tension between Eldridge and Jake, who were uncomfortable with the idea of living together. To resolve this, Charlie offered them money as a bribe, with additional incentives for each month they continued to live together.

When Alan moves out, he crosses paths with Melissa and, in a moment of deceit, lies about his relationship with Lyndsey, engaging in a brief affair with Melissa before confessing the truth over text. He returns to Lyndsey, only to set her house ablaze with a smoking pipe, only to find himself back at Charlie’s beach house, this time accompanied by Lyndsey, Eldridge, and Jake. Following this incident, Lyndsey grows distant from Alan, and when her ex-husband Chris McElroy proposes they reconnect, she rejects him. However, she reaches out to Alan, and they reconcile.

On Lyndsey’s birthday, Alan endeavors to find a meaningful gift for her but falls short. Desperate, he resorts to stealing earrings from Judith’s jewelry box, which he had given to Lyndsey before their marriage but she never wore. He later steals another necklace.

Lyndsey’s final appearance in Season 8 is in "Skunk, Dog, Crap and Ketchup," where she and Charlie bond over a conversation about sports betting. During this time, she reveals her job as a sports bookie in Vegas. Alan believes that his connection with Charlie is romantic, given Charlie’s history of taking Alan’s previous girlfriends. A heated argument ensues, but their relationship is rekindled. Alan later spies on them at a party, where he is not invited, despite Charlie explaining Lyndsey’s feelings towards him and offering him another chance. Alan, however, continues to harbor suspicions and accuses them of being unfaithful.

In "People Who Love Peepholes," Evelyn questions Alan about why he hasn’t moved in with Lyndsey, to which Alan responds that Lyndsey’s presence causes him severe discomfort, attributing it to PMS.

They reconcile in "Nine Magic Fingers," but Alan confesses his past indiscretions, including stealing Lyndsey’s diamond earrings. He claims they were taken from Judith, leading Lyndsey to kick him out. Despite her apologies, Alan confesses again, this time about hosting a party with at least 20 half-naked women, which results in another eviction.

In "Frodo’s Headshots," Alan dreams of Lyndsey seeking him out after their breakup, and they end up having sex. According to Alan, Lyndsey has a new boyfriend.

Lyndsey returns in "A Possum on Chemo," where she and Alan rekindle their relationship.

When conflict arises between Lyndsey and Zoey, sparked by insults, Walden and Alan step in to mediate, ensuring the situation doesn't escalate for the sake of everyone in the household. A storm ensues, leading to a sinkhole that closes the roads for 48 hours. This tension is further heightened when a near-fought between the two women over insults involving their children. Additionally, a power outage exacerbates the situation, making the atmosphere even more charged. Alan is ordered by Lyndsey to retrieve her tampons, a request he reluctantly complies with, fearing Lyndsey's wrath. Walden decides to accompany him, hoping to diffuse the tension by leaving Zoey out of the loop, believing she thinks Walden is on Lyndsey's side. Meanwhile, the boys are left to endure the rain, while the girls find solidarity in each other, recognizing they both have had difficult pasts with marriages and have independently moved up in their romantic lives.

In "Four Balls, Two Bats and One Mitt," Alan and Lyndsey decide to take their relationship to the next level by engaging in a threesome. Initially, they plan to involve Walden, followed by another girl of Alan's choosing. Alan shares their plans with Walden, who agrees to participate. However, the night in bed takes an unexpected turn as Lyndsey becomes overly focused on Walden, leaving Alan feeling uncomfortable, and Walden, still haunted by his past with Zoey, begins to cry.

In "I Scream When I Pee," Lyndsey and Alan part ways after Lyndsey discovers press photos of Alan and Kandi together. Kandi visits Lyndsey's house, reassuring her that nothing inappropriate happened between her and Alan. This shared understanding leads to Lyndsey and Kandi bonding over their mutual dissatisfaction with Alan's sexual prowess. The conversation veers into intimacy, and Lyndsey confesses, "Alan can never find out about this," to which Kandi agrees.

Towards the season's end, Lyndsey ends her relationship with Alan, feeling that the spark has faded.

In "I Think I Banged Lucille Ball," Lyndsey starts dating Larry, who struggles in the bedroom, leading her to occasionally sleep with Alan. She justifies this by claiming she's not interested in returning to him.

And in "Clank, Clank, Drunken Skank," Lyndsey suggests that Alan spend time with a woman named Stephanie. However, Alan ends up sleeping with her, leaving Lyndsey shocked and leaving the house.

Also in "Alan Harper, Pleasing Women Since 2003," Alan meets Lyndsey's boyfriend, Larry. To avoid causing a rift with Lyndsey, Alan adopts the persona of "Jeff Strongman" when referring to himself, ensuring Larry doesn't break up with Lyndsey. They form a bond and spend time together, which makes Lyndsey happy. She asks Larry to retrieve something from her car, intending to confront Alan directly. However, they end up having sex in the suite's restroom.

In "Dial 1-900-Mix-A-Lot," after Gretchen discovers Alan's true identity, she urges him to tell the truth to Larry, while Lyndsey advises against it, fearing Larry would call off the wedding. However, Alan decides to reveal the truth. As Lyndsey had feared, Larry cancels the wedding, and Gretchen accepts Alan's proposal. Yet, in "Oh, Wald-e, Good Times Ahead," Alan decides to disclose the truth to Larry. As expected, Larry calls off the wedding. Lyndsey realizes she has lost both Alan and Larry, leading to a mental breakdown. She resorts to extreme measures, such as placing their photos on pillows, talking to them in the bathroom of a restaurant, and going to a wedding to retrieve Alan.

In Glamping in a Yurt Walden and Alan prepare to adopt a child by pretending to be a gay couple. Jenny moves in with Evelyn while they prepare for adoption. Lyndsay returns after rehab and wants to get back together with Alan. Alan breaks the news that he is now married to Walden. A drunk Lyndsay wants to have sex with Alan on the side if Alan only married Walden to help get a child. Jenny distracts the social worker and they are approved to adopt.

In Bouncy, Bouncy, Bouncy, Lyndsey, Herb has just finished Alan's physical exam and has advised him that he needs to exercise more. He recommends that Alan join his yoga class, highlighting the additional perk of being in a setting filled with attractive women. Among them is Lyndsey. As Alan and Lyndsey engage in a brief argument, Herb inquires if he could pursue Lyndsey, given their past relationship. Despite acknowledging it would be inappropriate and a breach of the "bro code," Alan later discovers that Herb did, in fact, sleep with Lyndsey after he went to apologize to her.

Lyndsey returns some of Alan's belongings when she announces her decision to move away for a fresh start. After spending the night together, Alan asks her to consider getting back together, to which she responds that she'll think about it. Walden becomes concerned because he is dating Ms. McMartin, their adoption case worker, who has a "1" for him after he expresses his desire to break up. She unexpectedly shows up in the middle of the night for a surprise inspection and follows Alan on a date with Lyndsay. Lyndsay is upset because Alan didn't inform her about his other relationship. Alan seems to win Lyndsay back when he shows up at her house with a boom-box, playing "Say Anything," signaling that he's ready to make amends.

After Alan and Lyndsey reconcile, Lyndsey begins her search for an apartment and then proposes that Alan move in with her. However, Alan is not satisfied with any apartment and confesses that his ideal home is Walden's beach house. Lyndsey leaves after he chooses the beach house over her. Walden and Ms. McMartin mutually decide to end their relationship, and Walden officially adopts Louis. Realizing that they are destined to be alone together and that their respective partners are perfect for them, Alan chases after Lyndsey at the airport. Walden, after being serenaded by Michael Bolton, convinces Ms. McMartin to give him another chance. However, Alan's moment of joy is cut short when he is tasered by a TSA guard while expressing his love for Lyndsey. As both couples start to get along, Walden decides he wants a divorce from Alan and to move on. Walden grants Alan a wish as a token of his appreciation for his help in adopting Louis. Alan receives a Ferrari, which Lyndsey is upset about, as she and Walden believe Alan should have wished for something that included Lyndsey. Alan decides to propose to Lyndsey, especially after Walden offers to buy the engagement ring. Walden offers his full support but becomes anxious about the possibility of ending up alone if he allows Alan to move out. Alan proposes, and Lyndsey initially hesitates, but she eventually says yes, captivated by the large diamond in the ring.

In the series finale Lyndsay is seen pawning the engagement ring when Alan calls her on the phone after being scared about his brother coming to get him

Trivia

• Lyndsey's home is located on the same street as Judith's, making them neighbors.
• Lyndsey was a close family friend and neighbor to Alan and Judith when they were married, and their relationship remains strong.
• She has a history of infidelity, often having sex with more women than men. For instance, she had an affair with Alan's ex-wife, Kandi, and deceived Alan's boyfriend, Larry, by having sex with Jenny. She has cheated on Alan with Kandi, Larry, and Jenny, and has also cheated on Larry with Alan. Interestingly, her ex-husband has also betrayed her.
• Lyndsey takes great offense to Alan if he cheats, a testament to his weak resolve. Like Alan, Lyndsey harbors a fear of being alone, which is why she is open to dating anyone who shows interest in her.
• Lyndsey shares many traits with Alan, including a fear of being alone and a readiness to date anyone who is willing to spend time with her