Bonnie Winston began her career as a matchmaker at the age of 16. While dancing with her friends at a New York City club in 1979, she set up one of her friends with a guy Winston had met. Six years later, the matched couple got married. Winston unofficially continued the practice for the next 30 years—successfully matching hundreds of couples. In 2013, she made it official by creating a business, aptly named Bonnie Winston Matchmaker.
When her first client, a woman in the entertainment business, asked to see the men in Winston’s database, Winston said, “I don’t work that way.” She then explained, “Tell me your dating criteria, and I will go out and find him.” Winston found the woman a man who fit her description, and then she provided her coaching for six weeks while they dated. A year later, the couple got engaged.
Impressed with Winston’s relationship-matching ability, the client referred celebrities looking for love to Winston’s business. “So that’s how I became a celebrity [matchmaker],” Winston says, though she’s also happy to find a partner for those without all the fanfare. Her tagline, “I find mates, not just dates,” references the fact that she isn’t a dating service; rather, she considers herself a matchmaker.
Winston’s matchmaking skills debut on The Marvelous Mrs. Maisel
One of Winston’s clients asked if she’d be willing to provide consultation to Marin Hinkle on how to be a matchmaker. Hinkle plays the role of Rose Weissman, a matchmaker and Miriam Maisel’s mother, on the television show The Marvelous Mrs. Maisel.
Winston thinks Hinkle did an excellent job playing a matchmaker on the show—in fact, Hinkle was nominated for an Emmy in 2020 for her role as Weissman.
“She really bought into the character. She played her very well,” Winston says. “And like her character in the show, I am a huge collaborator.”
With Winston’s expertise in matchmaking comes a sharp eye for discerning qualities that wouldn’t make someone a good match. Here, she shares her top relationship red flags to look out for when dating.
9 relationship red flags
1. Your friends and family don’t like your partner.
“I believe everybody has an intuition,” Winston says. She explains that if the people in your life who care about you don’t like the person that you are dating, then it’s a red flag. “If you’re physical with someone, your intuition like everything else goes out the window,” she says.
Since you may be wearing rose-colored glasses and not thinking clearly, it’s important to trust the opinion of those who know you. But if it’s only one friend or family member who doesn’t like the person that you are dating, it’s possible that you don’t need to fret over your significant other. Only if several people you know are saying that they don’t like your person, then you should probably stop to inspect the relationship a bit closer.
2. A history of falling in love fast is a relationship red flag.
If they have been married multiple times within a short time frame, that could be a red flag. “They’ve been married three times but they’re like, ‘Well, the first was a starter. And the third was after my money and they didn’t take any accountability.’ That’s a red flag,” Winston says.
3. They don’t communicate.
Winston explains that you should be wary of someone who has trouble expressing their feelings and communicating with you. “They never say those three words, which [are], ‘I love you’ and they’re not communicative. That’s a red flag,” she explains.
4. They only care about themselves is a red flag in a relationship.
If your partner is self-centered and doesn’t take the time to ask you any questions about your life, that is a “big red flag,” according to Winston. “Someone that doesn’t really ask about you and is constantly speaking about themselves,” is something that should concern you.
Winston adds that over time you will say, “‘Oh, my God, that guy was such a narcissist,’” and will realize that “they never asked you anything about themselves because they really don’t care about anything, except themselves.”
5. They travel a lot but don’t stay in touch.
Your partner might have to travel a lot for work but it’s easy to keep lines of communication open with the various forms of technology available at our fingertips. “A red flag is if they’re traveling a lot, but they’re not in touch with you,” Winston says. She explains that even if your partner is busy, it’s easy to send a quick text message. “There has to be a balance,” she says.
6. A lack of consistency is a relationship red flag.
If the person you are dating doesn’t communicate with you during the week, that’s a cause for concern. “If somebody is just showing up at your house, and then going to work and there’s nothing in between the dates, then I think that’s a red flag,” Winston says, adding that there has to be consistency and regular communication with your partner.
7. They don’t trust you.
You should be concerned if your partner doesn’t trust you. “If they’re always questioning you, then that’s never going to go away,” Winston says. She explains that possessiveness is not healthy, and it’s necessary for the person you’re dating to trust you to have a healthy relationship.
8. They’re not allowing you to come into their life.
It’s a red flag if you have invited your partner into your life and they are not reciprocating. Consider whether you know or have been introduced to any of their friends or family. If that’s been a barrier, you should wonder why. “You’re introducing your life, your friends and they have never brought you into their life and they have a life? Then that’s a red flag,” Winston explains.
9. They are older and never had a relationship can be a red flag.
There are some exceptions here, but in general, you may want to be cautious if someone is older and never had a relationship. Winston has worked with a 65-year-old client who fell into this category. This person, and others who’ve never had relationships, tend to be unrealistic. “I have a client right now and she wants a unicorn and they don’t exist,” Winston says.
Winston’s words for the dating challenges
If Winston’s clients are having trouble dating, she does provide coaching and is “on-call” for her clients. “My hours are like clergy. People are calling me, texting me and I just finished dinner,” she says.
She takes an individualized approach with each client, and if she believes they might require some more help, she’ll refer them to counseling. But she is always willing to try to help people find love.
“We’re trying. We’re hopeful,” she says.
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