Taking a Date Home for the Holidays All Episodes

Thirty years ago, successful entrepreneur Richard Sterling was set up and spent a passionate night with a country girl who vanished by morning. Now nearly 50 and a billionaire, he remains unmarried, still haunted by her memory. Hoping to cure his loneliness, his niece signs him up for a matchmaking event, having him pose as a security guard to hide his wealth. Richard Sterling attends just for fun, unimpressed by his dates—until he unexpectedly falls in love at first sight with a woman his age, Helen...

Thirty years ago, successful entrepreneur Richard Sterling was set up and spent a passionate night with a country girl who vanished by morning. Now nearly 50 and a billionaire, he remains unmarried, still haunted by her memory. Hoping to cure his loneliness, his niece signs him up for a matchmaking event, having him pose as a security guard to hide his wealth. Richard Sterling attends just for fun, unimpressed by his dates—until he unexpectedly falls in love at first sight with a woman his age, Helen...

Thirty years ago, successful entrepreneur Richard Sterling was set up and spent a passionate night with a country girl who vanished by morning. Now nearly 50 and a billionaire, he remains unmarried, still haunted by her memory. Hoping to cure his loneliness, his niece signs him up for a matchmaking event, having him pose as a security guard to hide his wealth. Richard Sterling attends just for fun, unimpressed by his dates—until he unexpectedly falls in love at first sight with a woman his age, Helen...

Thirty years ago, successful entrepreneur Richard Sterling was set up and spent a passionate night with a country girl who vanished by morning. Now nearly 50 and a billionaire, he remains unmarried, still haunted by her memory. Hoping to cure his loneliness, his niece signs him up for a matchmaking event, having him pose as a security guard to hide his wealth. Richard Sterling attends just for fun, unimpressed by his dates—until he unexpectedly falls in love at first sight with a woman his age, Helen...

Thirty years ago, successful entrepreneur Richard Sterling was set up and spent a passionate night with a country girl who vanished by morning. Now nearly 50 and a billionaire, he remains unmarried, still haunted by her memory. Hoping to cure his loneliness, his niece signs him up for a matchmaking event, having him pose as a security guard to hide his wealth. Richard Sterling attends just for fun, unimpressed by his dates—until he unexpectedly falls in love at first sight with a woman his age, Helen...

Thirty years ago, successful entrepreneur Richard Sterling was set up and spent a passionate night with a country girl who vanished by morning. Now nearly 50 and a billionaire, he remains unmarried, still haunted by her memory. Hoping to cure his loneliness, his niece signs him up for a matchmaking event, having him pose as a security guard to hide his wealth. Richard Sterling attends just for fun, unimpressed by his dates—until he unexpectedly falls in love at first sight with a woman his age, Helen...

Thirty years ago, successful entrepreneur Richard Sterling was set up and spent a passionate night with a country girl who vanished by morning. Now nearly 50 and a billionaire, he remains unmarried, still haunted by her memory. Hoping to cure his loneliness, his niece signs him up for a matchmaking event, having him pose as a security guard to hide his wealth. Richard Sterling attends just for fun, unimpressed by his dates—until he unexpectedly falls in love at first sight with a woman his age, Helen...

Thirty years ago, successful entrepreneur Richard Sterling was set up and spent a passionate night with a country girl who vanished by morning. Now nearly 50 and a billionaire, he remains unmarried, still haunted by her memory. Hoping to cure his loneliness, his niece signs him up for a matchmaking event, having him pose as a security guard to hide his wealth. Richard Sterling attends just for fun, unimpressed by his dates—until he unexpectedly falls in love at first sight with a woman his age, Helen...

Thirty years ago, successful entrepreneur Richard Sterling was set up and spent a passionate night with a country girl who vanished by morning. Now nearly 50 and a billionaire, he remains unmarried, still haunted by her memory. Hoping to cure his loneliness, his niece signs him up for a matchmaking event, having him pose as a security guard to hide his wealth. Richard Sterling attends just for fun, unimpressed by his dates—until he unexpectedly falls in love at first sight with a woman his age, Helen...

Thirty years ago, successful entrepreneur Richard Sterling was set up and spent a passionate night with a country girl who vanished by morning. Now nearly 50 and a billionaire, he remains unmarried, still haunted by her memory. Hoping to cure his loneliness, his niece signs him up for a matchmaking event, having him pose as a security guard to hide his wealth. Richard Sterling attends just for fun, unimpressed by his dates—until he unexpectedly falls in love at first sight with a woman his age, Helen...