Flirting Tips for Midlife Daters

If you’re dating again after 40, you may need to brush up on your flirting. In this short video, I share simple—yet powerful—flirting tips.

When it comes to flirting, a lot of people who are returning to the dating pool in midlife feel out of practice and uncomfortable. How do you flirt without it feeling awkward or fake? In this short video I filmed for Bottom Line, Inc., I offer a few flirting tips to help you be more successful at this thing we call love!

Note: Flirting is not necessarily an invitation for sex. And you don’t have to be fake. Instead, it is a way to convey subtle, focused attention. Flirting can include offering compliments, being playful, lightly touching your date’s forearm (but don’t overdo it!). And the best flirting tip of all…smile.

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Dating in Midlife: The Importance of STI Screening

STI screening

If you’re sexually active, it’s important to have STI screening. Check out this comprehensive study on sexually transmitted infections.

Every year in the United States, more than 20 million new sexually transmitted infections (STIs) are reported, half of which occur in young people between the ages of 15 and 24. Reports from the Centers for Disease Control and Prevention also show that one out every 208 people in America has chlamydia, equating to more than 1.5 million people.

These statistics show just how frighteningly common STIs are and indicate a degree of naivety about sex, especially amongst midlife daters. A one-night stand may be spontaneous, but it could easily lead to undesirable long-lasting consequences. Likewise, if you or your partner in a relationship don’t fully know each other’s sexual history before engaging in intercourse, there could be some horrific news to be broken in the future.

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When to Start Dating After Divorce?

Many experts say wait at least a year before dating after divorce, but is this really a one-size-fits-all issue? Check out this infographic and find out!

Getting back into the dating game can be tough, especially after a divorce. There is of course no one-size-fits-all way to decide when to start dating after a divorce, but you do need time to heal. A year might be the sweet spot for many, but only you will know when you’re ready to date again.

I believe it’s important for us to identify our contribution to a failed marriage. Not for the purpose of blaming, but because we attracted this person into our life for a reason.

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Do You Need a Prenup When Remarrying in Midlife?

When remarrying in midlife, how important is it to get a prenup? In this short video for Bottom Line, Inc., I share my thoughts on prenups…

When people are remarrying in midlife, they have financial obligations, assets and situations that they might not have had to worry about the first time around, and they wonder if they might need a prenuptial agreement. In this short video I filmed with Sarah Hiner, President of Bottom Line, Inc., I suggest that prenuptial agreements are a must-have in all marriages.

While some people view them as insulting and a suggestion that the marriage might not work out, I believe that people need to protect their hard-earned finances and be able to talk about everything as they prepare for marriage. If you are close enough to someone to marry them, you are certainly close enough to discuss a prenup.

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What’s an Acceptable Age Difference When Dating in Midlife?

Do all men over 40 date much younger women? Watch this video to hear my thoughts on an acceptable age difference when dating in your 40s, 50s and beyond.

In this video, I talk with Sarah Hiner, President of Bottom Line, Inc., about the age range when dating in in your 40s and beyond. What is an acceptable age difference when dating in midlife? I suggest that age isn’t nearly as important as an interpersonal connection when it comes to dating. While it is true that someone who is much younger might not have the same cultural references, level of maturity, or life skills, this doesn’t mean that a legitimate connection is not possible. Let go of limiting beliefs, and you’ll greatly increase your chances of meeting compatible people.

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A 52-Year-Old Guy Dishes on Dating in New York City

The one thing that threw this divorced single dad for a loop? Dating in New York City in his fifties. Turns out it can be both challenging and fun. 

My radio guest, Matt Sweetwood, is the U.S. CEO and President of beBee, Inc. He is well known for his innovative and transformative ideas in marketing, social media, and business development. He was President of Unique Photo, NJ’s premiere camera store, for over 28 years. However, by far, his greatest achievement is having raised five successful children to adulthood as a single dad. He’s the creator of the Man-Up Project, helping other men though fatherhood and life. He is a regular contributor on national TV and to several publications in the social media, photography, business, ethics, politics and parenting arenas.

52-year-old Matt recently moved to Manhattan after living his entire life in New Jersey. We had a lively discussion about his experience with dating in New York City in midlife. Read highlights below of episode #258: A Manhattan Middle Aged Man’s View of Dating. 

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