Is It Love or Is He Just After Your Assets? Dating Over 50, You Be the Judge episode artwork

EPISODE · May 30, 2026 · 12 MIN

Is It Love or Is He Just After Your Assets? Dating Over 50, You Be the Judge

from Dating to Win · host Matt Russo

Dating over 50 can get complicated fast — especially when you have to ask: Is this love, or is someone after my assets? In this episode of Dating to Win, Matt Russo tries something different. Since starting the romance scam series, Dating to Win has received more emails from viewers over 50 who are dealing with real dating issues later in life — including money concerns, adult children, loneliness, second chances, trust, financial red flags, and whether it is safe to open your heart again. Today, Matt reads several viewer email questions, but he is not giving his advice yet. You are. Listen to each dating dilemma and then share what you would tell them. Should they stay? Should they walk away? Should they protect their money? Should they listen to their adult children? Should they protect their peace? Or should they take a chance on love? In a future episode, Matt will read some of the audience comments, share the best advice from viewers, and then give his own opinion on what each person should do For dating questions, guest stories, interview requests, or to share your own dating dilemma: Email: [email protected] Subscribe to Dating to Win: https://www.youtube.com/@DatingtoWin25?sub_confirmation=1 Watch more Dating to Win videos: https://www.youtube.com/@DatingtoWin25/videos TikTok: https://www.tiktok.com/@date2win    

Episode metadata supplied by the publisher feed · Published May 30, 2026

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Dating over 50 can get complicated fast when love, money, adult children, trust, and financial red flags all collide. In this interactive episode, Matt reads viewer dating dilemmas and asks the audience to be the judge.

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Is It Love or Is He Just After Your Assets? Dating Over 50, You Be the Judge

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