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Macaulay Culkin’s Second Proposal to Brenda Song Involves Their Two Sons

5/2/2026, 5:19:39 AM

The August Re-Proposal: Details of the Event

In August, actor Macaulay Culkin staged a second marriage proposal to his longtime partner, actress Brenda Song. The proposal was coordinated with their two sons, Dakota (5) and Carson (4). Flowers were placed at the front door, and the children participated directly. When Culkin asked Song, “OK what do you say to mama?” the youngest responded, “Ram’s House!”—a reference to Song’s support for the Los Angeles Rams.

Relationship Background: From Co-Stars to Parents

Culkin, 45, is best known for his role in *Home Alone*. Song, 38, gained prominence through the series *Running Point*. The pair have been together for several years and share two children, Dakota and Carson. Their partnership has been publicly documented through various media appearances, including Song’s recent podcast interview.

Key Figures: Profiles of the Family Members

  • Macaulay Culkin – Actor, age 45, initiator of the August re-proposal.
  • Brenda Song – Actress, age 38, recipient of the proposal; discussed the event on the *Not Gonna Lie* podcast.
  • Dakota Culkin – Son, age 5, participated in the flower arrangement.
  • Carson Culkin – Son, age 4, contributed the “Ram’s House!” response.

Chronology of the Proposal

  • August 2023 – Culkin’s second proposal takes place at the family home with the involvement of Dakota and Carson.
  • April 30, 2024 – Song recounts the proposal on the *Not Gonna Lie* podcast, describing the moment and the children’s roles.

Data & Statistics

  • Parents: Culkin 45, Song 38.
  • Children: Dakota 5 years old, Carson 4 years old.
  • Event: One proposal, two children, floral décor at the front door.

Why the Re-Proposal Draws Public Interest

The public re-engagement of two well-known actors, combined with the active participation of their young children, creates a narrative that blends celebrity romance with family dynamics. Media coverage highlights the novelty of a second proposal and the inclusion of a sports-team reference, adding cultural relevance.

Official Statements & Responses

During the *Not Gonna Lie* podcast, Song explained that she was returning home from a *Running Point* shoot when her mother texted her about makeup. She described walking up to the front door, seeing the flowers and her sons, and hearing Culkin’s question. Song noted that her children are accustomed to “callbacks,” prompting her to ask, “Who’s house?” and receiving the answer, “Ram’s House!” She emphasized that the children’s involvement was intentional and reflected her enthusiasm for the Rams.

Criticism & Opposition

The provided sources contain no critical commentary or opposing viewpoints regarding the proposal.

Verbatim Quotes

  • “I was coming home from Running Point and my mom texts me,” — Brenda Song, actress
  • “I walk up and I’m like ‘Oh my God’ and he looked at my boys and he goes, ‘OK what do you say to mama?’” — Brenda Song
  • “He’s so used to me doing callbacks because I’ll go, ‘Who’s house?’” — Brenda Song
  • “And he’ll go, ‘Ram’s House!’ I’ve trained my kids well.” — Brenda Song

What’s Next

No further events or announcements related to the couple’s plans have been disclosed in the available sources.