"Alan can never know about this."
|Lyndsey and Kandi agreeing, after the two have sex.|
Lyndsey Ruth Anne McElroy is a major recurring character of Two and a Half Men from Season 7 onwards. She is the mother of Eldridge McElroy; who is a friend of Jake Harper; and is in an on-off relationship with Alan.
Lyndsey McElroy is an average height, fair haired, attractive woman with a slim figure. Her looks remain this way all through the series. Through the series she ages minorly, but still keeps her figure.
Lyndsey has always come off as slightly masculine judging by her enjoyment of drinking beer. Lyndsey has a drinking problem and that became apparent after she vomits all over the inside of Walden's private jet, after getting deliriously drunk.
While she was in high school, Lyndsey desperately needed money and consequently appeared in a soft-core pornography film entitled "Cinnamon Buns". It included a bakery shop scene where she was covered in frosting. Herb Melnick discovers this film and fantasizes about her being naked. Lyndsey confirms her past to Charlie and Alan.
She lost her virginity back stage at a Police concert. Her lover was not named, but she claimed her first time "stinged a little bit".
Lyndsey first meets Alan in the episode "Keith Moon Is Vomiting In His Grave", where she is introduced as Eldridge’s mother. Whilst Alan’s original intentions were to tell Eldridge on her, he is stunned by her beauty, and instead goes out with her for a drink. They then wind up having sex in the toilet. She then starts seeing him regularly, and the two start dating. Due to either of them not being able to get alone time at either of their homes, Alan buys a hotel room for their private time. However, the date doesn’t go as planned, as Lyndsey suffers a period. She does appreciate Alan’s patience with her, and the two grow fond of each other. They intend to keep their relationship hidden from their children.
Lyndsey and Alan’s get-together is found out by Jake and Eldridge. After asking for forgiveness, Alan and Lyndsey dine together with their children, and announce their relationship to them. Lyndsey later on asks Alan to move in with her. Though initially reluctant to do so, Alan accepts when he realizes that it will annoy Judith. Trouble arises when Eldridge and Jake are not comfortable in staying with each other, to which Charlie bribes them with $ 500 and $ 100 for every month they continue the practice.
When Alan moves out, he meets Melissa, and lies about his relation with Lyndsey, having sex with Melissa a couple of times before texting her about the truth. He returns to Lyndsey fulltime, only to burn her house with a smoking pipe, and once again moving back into Charlie’s beach house, this time with Lyndsey and Eldridge accompanying him and Jake. Lyndsey becomes cold towards Alan after the incident, and when her ex-husband Chris McElroy asks her to talk with him (conceiving the idea that they might get back together), she leaves him. However, she calls Alan, as things do not work out with Chris, and they get back together.
On Lyndsey’s birthday, Alan works very hard to get her a decent birthday gift, but fails. He ultimately steals earrings from Judith’s jewelry box, which he got her just before their marriage ended, and she never used them. He later on also steals a necklace.
Lyndsey’s final appearance of Season 8 is in "Skunk, Dog, Crap and Ketchup", where she and Charlie bond over a chat regarding sports betting, where she revealed that she works for a sports bookie in Vegas. Alan thought that her bond with Charlie was romantic, as Charlie had stolen many of Alan’s past girlfriends. Alan and Lyndsey have a heated discussion, after which they relationship seizes again. Alan later spies on her and Charlie at her party, where he doesn’t get invited. Though Charlie explains to Lyndsey that Alan’s reaction are valid; and to give him another chance, Alan catches them again, assuming his suspicions are true, and calls them Bastard and Slut.
Lyndsey is mentioned by Evelyn in "People Who Love Peepholes". When Alan moves in with Evelyn, she questions him not moving in with his Lyndsey, to which Alan replies that it is not a good time, as they currently have clashes.
They get back together in "Nine Magic Fingers" but in the next episode Alan confesses every embarrasing thing he did but the last one was that the the diamond earrings he gave to her were stolen from Judith cause her to kick Alan out. She later apologizes but Alan confesses again that he was having a party with at least 20 half naked chicks which causes Alan to get kicked out again.
She re-appeared in "A Possum on Chemo" as she and Alan rekindled their relationship.
In "Four Balls, Two Bats and One Mitt", Alan and Lyndsey decide to progress their relationship further by having a threesome. First, it will be with Walden and then again with another girl of Alan's choice. Alan tells Walden about their plan and Walden agrees to participate. That night, in bed, the threesome goes awry with Lyndsey paying more attention to Walden, making Alan uncomfortable and Walden begins crying as he is still not over Zoey. The next night, at Pavlov's, Alan picks up a woman with Lyndsey's help, but the other threesome is derailed when she meets Walden.
In "I Scream When I Pee", Lyndsey and Allan break-up over Lyndsey finding press pictures of Alan and Kandi together. Kandi then goes over to Lyndsey's house explaining that nothing happened between her and Alan. They women bond over agreeing that Allan isn't very good in bed. The conversation leads to Lyndsey and Kandi having sex. In bed, Lyndsey looks surprised and or shocked at herself and Kandi just looking as she always does. Both women agree that:"Alan can never know about this."
Towards the end of the season, Lyndsey breaks up with Alan when the spark in their relationship is gone.
In "I Think I Banged Lucille Ball", Lyndsey starts dating a man named Larry and he is not good in bed so she sometimes sleeps with Alan and she claims she's not getting back with him.
And in "Clank, Clank, Drunken Skank" She suggests Alan to hang out with a woman named Stephanie but he ends up sleeping with her and he tells Lyndsey who is aghast and leaves the house.
Also in "Alan Harper, Pleasing Women Since 2003", Alan meets Lyndsey's boyfriend Larry which Alan refers himself as "Jeff Strongman" so Larry doesn't flip out and dump Lyndsey. They bond and hang out together which makes Lyndsey pleased. She asks him to retrieve something from her car to confront Alan directly, but the two wind up having sex in the suite's restroom.
However, in "Oh, Wald-e, Good Times Ahead", Alan ends up telling him anyway. As she expected, Larry called off the wedding and Gretchen accepted Alan's proposal. When Lyndsey realizes that she lost both Alan and Larry, she goes through a mental breakdown by putting their pictures on pillows and talking to them, invading a restaurant's bathroom to "accept" Alan's "proposal", and going drunk to his marriage in order to retrieve him.
Relationships with other people
- Lyndsey's home is situated on the same street of Judith’s, making them neighbors.
- Lyndsey was a family friend and neighbor to Alan and Judith when they where married and still remains a close neighbor to Judith and Herb.
- Lyndsey is Alan's on-and-off girlfriend throughout the series.
- Lyndsey slept with Alan's ex-wife, Kandi, after they supposedly break-up for the last time.
- It seems Lyndsey repeatedly cheats: She cheated on Alan multiple times, with Kandi, Larry, and Jenny, and she has cheated on Larry with Alan. In the other hand, her ex-husband cheated on her.