Expert Q&A for How to Date a Millionaire

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  • Question
    Should I offer to pay on a date?
    Alessandra Conti
    Celebrity Matchmaker & Dating Coach
    Alessandra Conti is a Celebrity Matchmaker, Dating Coach, and Co-Founder of Matchmakers In The City, a personal Matchmaking firm headquartered in Los Angeles, California. Alessandra is a Matchmaker behind MTV's, “Are You The One”, and is the go-to Celebrity Matchmaker for shows like NBC's Access Hollywood, and CBS's Face The Truth. Her dating and relationship advice has been featured on Forbes, Elite Daily, The New Yorker, The LA Times, and Fox News. For nearly 10 years, Alessandra has worked with clients ranging from celebrities to young professionals and leads a team of matchmakers responsible for hundreds of marriages through their knowledge of interpersonal relationships, body language, and lie detection. She holds a BA in Communications from American University and is a Matchmaking Institute Certified Matchmaker (CMM).
    Celebrity Matchmaker & Dating Coach
    Expert Answer
    It depends. If you're inviting your date somewhere, you should be treating them. However, your date should pay if they're the one planning the event. In some cases, your date might stop you from footing the bill and insist on paying themselves.
  • Question
    I'm nervous about asking out someone I like. Do you have any tips?
    Alessandra Conti
    Celebrity Matchmaker & Dating Coach
    Alessandra Conti is a Celebrity Matchmaker, Dating Coach, and Co-Founder of Matchmakers In The City, a personal Matchmaking firm headquartered in Los Angeles, California. Alessandra is a Matchmaker behind MTV's, “Are You The One”, and is the go-to Celebrity Matchmaker for shows like NBC's Access Hollywood, and CBS's Face The Truth. Her dating and relationship advice has been featured on Forbes, Elite Daily, The New Yorker, The LA Times, and Fox News. For nearly 10 years, Alessandra has worked with clients ranging from celebrities to young professionals and leads a team of matchmakers responsible for hundreds of marriages through their knowledge of interpersonal relationships, body language, and lie detection. She holds a BA in Communications from American University and is a Matchmaking Institute Certified Matchmaker (CMM).
    Celebrity Matchmaker & Dating Coach
    Expert Answer
    Don't overthink it! Men are pretty straightforward when it comes to expressing themselves and wanting to date someone. The best thing you can do is just ask them out on a date directly. Say something like "Hey, I think you're amazing. I would love to take you out to dinner on Friday, are you free?" Just go for it!
  • Question
    How can I show appreciation for my partner who makes a lot more money than me?
    Alessandra Conti
    Celebrity Matchmaker & Dating Coach
    Alessandra Conti is a Celebrity Matchmaker, Dating Coach, and Co-Founder of Matchmakers In The City, a personal Matchmaking firm headquartered in Los Angeles, California. Alessandra is a Matchmaker behind MTV's, “Are You The One”, and is the go-to Celebrity Matchmaker for shows like NBC's Access Hollywood, and CBS's Face The Truth. Her dating and relationship advice has been featured on Forbes, Elite Daily, The New Yorker, The LA Times, and Fox News. For nearly 10 years, Alessandra has worked with clients ranging from celebrities to young professionals and leads a team of matchmakers responsible for hundreds of marriages through their knowledge of interpersonal relationships, body language, and lie detection. She holds a BA in Communications from American University and is a Matchmaking Institute Certified Matchmaker (CMM).
    Celebrity Matchmaker & Dating Coach
    Expert Answer
    Words of affirmation go a long way. Verbally tell them how much you appreciate them taking you to dinner or on trips. Figure out their love language and tailor your appreciation - it could be physical touch, quality time, or acts of service too. Little gifts here and there, like paying for parking or coffee, are also nice gestures to show you care.
  • Question
    What do rich guys look for in women?
    Alessandra Conti
    Celebrity Matchmaker & Dating Coach
    Alessandra Conti is a Celebrity Matchmaker, Dating Coach, and Co-Founder of Matchmakers In The City, a personal Matchmaking firm headquartered in Los Angeles, California. Alessandra is a Matchmaker behind MTV's, “Are You The One”, and is the go-to Celebrity Matchmaker for shows like NBC's Access Hollywood, and CBS's Face The Truth. Her dating and relationship advice has been featured on Forbes, Elite Daily, The New Yorker, The LA Times, and Fox News. For nearly 10 years, Alessandra has worked with clients ranging from celebrities to young professionals and leads a team of matchmakers responsible for hundreds of marriages through their knowledge of interpersonal relationships, body language, and lie detection. She holds a BA in Communications from American University and is a Matchmaking Institute Certified Matchmaker (CMM).
    Celebrity Matchmaker & Dating Coach
    Expert Answer
    Even if the person is rich, they'll want someone who can hold their own financially rather than relying on them.
  • Question
    How do you know if someone is genuine on a dating site?
    John Keegan
    Dating Coach
    John Keegan is a Dating Coach and motivational speaker based in New York City. With over 10 years of professional experience, he runs The Awakened Lifestyle, where he uses his expertise in dating, attraction, and social dynamics to help people find love. He teaches and holds dating workshops internationally, from Los Angeles to London and from Rio de Janeiro to Prague. His work has been featured in the New York Times, Humans of New York, and Men's Health.
    Dating Coach
    Expert Answer
    If you're questioning if the person is truly a millionaire as they claim, taking a closer look at their profile might give you some clues. If they're over exaggerating about all their strong points, or it's overly well written, it can be a good sign of lying.
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