# Sophia Stallone engagement and wedding preparations > Live situation record from CLSTR: https://clstr.news/situations/sophia-stallone-engagement-and-wedding-preparations > Updated: 2026-10-20T14:30:00.000Z. Sources: 12. Developments: 3. Following the engagement of his eldest daughter, Sophia Stallone, to Michael Sheehan in August, actor Sylvester Stallone has shared details regarding the family milestone. Stallone initially described the engagement process, noting that Sheehan followed a traditional approach by formally asking for his permission, an act the actor found “unexpected and overwhelming.” He expressed high regard for Sheehan, calling him a “great guy,” a “stand-up guy,” and an “extraordinary” person. During recent appearances on ‘Live with Kelly and Mark’, the 80-year-old actor joked that the significant costs associated with the upcoming wedding mean he “can’t retire.” He remarked, “It’s almost embarrassing to say — but I can’t retire.” In addition to the actor's comments, reports indicate that his wife, Jennifer Flavin, has played a mediating role in family discussions regarding the marriage. ## Timeline ### 2026-10-20: Sylvester Stallone jokes about delaying retirement for daughter's wedding Sylvester Stallone joked on ‘Live with Kelly and Mark’ that he must delay retirement to fund his daughter Sophia's wedding. 2 sources. https://clstr.news/cluster/sylvester-stallone-jokes-about-delaying-retirement-for-daughters-wedding ### 2026-10-13: Sylvester Stallone says he cannot retire due to daughter's wedding costs Sylvester Stallone joked that he cannot retire because he must fund the upcoming wedding of his daughter, Sophia Stallone, to her fiancé Michael Sheehan. 8 sources. https://clstr.news/cluster/sylvester-stallone-says-he-cannot-retire-due-to-daughters-wedding-costs ### 2026-10-01: Sylvester Stallone discusses daughter Sophia’s engagement Sylvester Stallone recounted his surprise at Michael Sheehan’s traditional request for permission to marry his daughter, Sophia Stallone, following their engagement in August. 2 sources. https://clstr.news/cluster/sylvester-stallone-discusses-daughter-sophias-engagement --- Cite as: Sophia Stallone engagement and wedding preparations. CLSTR, https://clstr.news/situations/sophia-stallone-engagement-and-wedding-preparations