Baby Boomer Dating Tips for Successful Dating

baby boomer dating

Baby Boomer Dating Tips

Let’s face it: baby boomer dating is daunting. And when you’re in your 40s, 50s or 60s it may seem next to impossible. You might be coming out of a long-term marriage. Or emerging from a period of time where you were consumed with raising children. Or caring for elderly parents or perhaps you still are responsible for children and/parents. Have your “dating muscles” atrophied? You might feel like you don’t have the slightest idea how to go about flirting. Or meeting the opposite sex, much less handling issues of sexually transmitted diseases. You might feel like your body is old or unattractive. Disrobing in front of a romantic partner? Definitely not.

Baby Boomer Dating Questions

Here are some typical baby boomer dating and relationship questions that over 40s and 50s ask me. How proactive are women supposed to be? Is the third-date rule (for having sex) still in effect? Just how do you handle an HIV discussion? Is online dating reliable, safe, or even effective? And all these questions and difficulties are magnified for female Boomers. And they outnumber their male counterparts and also have to compete with younger women.

Yet many women, have gone out there and had the fun and excitement of their teenage years all over again. And with the wisdom of the years, baby boomer dating is even better! A 54 year-old artist who is in our dating coaching program recently e-mailed me about her new boyfriend. Joe adores me. He tells me I am a treasure, a rare beauty. I make him feel alive after so many years of being dead. Joe loves my voice, my thoughts, my work. He bought riding boots and we went riding together. His 95-year-old mom in Miami wants to see my photo.

Once you take the dating plunge, you may be very pleasantly surprised at the possibilities. Especially in online dating and dating apps. They often report that once they start, they feel more confident. And, more clear about what they want and therefore more attractive!

Female Boomers are more empowered and more affluent than ever before.

The good news is that often, younger women cannot compete with them for a mature guy’s attention. The thirty-somethings are too active and demanding in terms of nightlife and other activities, whereas many men may prefer the seasoned wise companionship of a woman who has been there and done that. In other words, both male and female Baby Boomers are in a position to pick and choose who they want to date.

Here’s what Shirley, a 50-year-old very successful divorcee who took advantage of a free 40-minute session with my expert dating coach. She went from being a hermit to dating two terrific guys:

I just met another amazing guy. This one actually was suggested by Match. I winked. He e-mailed. I e-mailed back. He called me and we had a fabulous conversation. He was so easy to talk , seemed honest and sincere. I asked some pretty blunt questions that he happily answered in good detail. And he’s tall! He created a business and sold it in 2006 because he had plenty of money and wanted to do something else. On the other hand, Bill, the writer, is coming out this afternoon. We are going to the beach. Bill says that he has written a poem for me.


Here are six baby boomer dating tips to help you succeed.

  • Baby Boomer Dating Tip #1. Take care of you.  

    For the outer (and inner) you, start a regular exercise program. It is definitely the fountain of youth. Give yourself a makeover so that you look great in your own eyes. Get that trendy haircut, go shopping, try out those clothes that your friend wears that give him or her a sexy, attractive or powerful look.

  • Baby Boomer Dating Tip #2. Don’t be shy to advertise.

    Then put out the word in your network that you are ready to date. Seventy-two percent of relationships come from a person’s network of friends, co-workers, and family. At first, don’t be picky — simply tell folks you are looking for a wonderful person.

  • Baby Boomer Dating Tip #3. Go where the singles go. 

    Go where the opposite sex (or same sex, if you prefer) is. If you like what you see, smile, make eye contact, give a sincere compliment or ask for some help. Sign up for on-going classes/activities that interest you and that have potential for baby boomer dating. For example, courses on finance, investing, sports and leadership; snowboarding/skiing; hiking; and cigar tasting usually have a lot of men in them. If you’re a mature male, women are attracted to growth, craft, cooking, or spiritual courses. If you’re not sure, ask the enroller about the ratio of men to women. There are many other fun activities, classes, and clubs to explore baby boomer dating so Google any class/topic plus “your city” and “classes.”

  • Baby Boomer Dating Tip #4. Definitely do not miss out on online dating & Dating Apps. 

    Meeting people online is essential because it gives you a sense of the wide variety of singles that are out there right now. About 40 million singles are dating online in the U.S. according to the latest independent research. You can partake of this smorgasbord of possibilities right there at your computer. Spend the time and work two sites. In addition to subscribing to a large site like Match, eHarmony or Tinder, subscribe to a more specialized site like christianmingle or Jdate. And for the best online baby boomer dating tips be sure to sign up for my free newsletter. A recent one featured a two part series on secrets of online dating success for over 40s and 50s.

  • Baby Boomer Dating Tip #5. Put some time into it.

    Most people spend more time planning a vacation than they do planning their dating lives. And they get great vacations and little-to-no love life! So if you want to date, get out your calendar and set aside 8 to 10 hours per week to spend on going to courses, working your online dating program and actually going out on dates.

  • Baby Boomer Dating Tip #6. Take a great head shot for successful online dating.

    Women, make sure you use a great head shot photo — men are very visual. Either get one done professionally that looks casual, or have a photographer friend take 100 shots to get just the right one. Digital cameras and even smartphones make it easy to take many photos, so you can choose the one that’s perfect.

  • My expert dating coaches specialize in online dating so that you get the best possible responses. And if you sign up for ongoing coaching I will personally write your online profile.

So now you have the six basic baby boomer dating tips. And for more, watch my PBS video on finding true love when you’re a boomer.

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Are you a successful woman who is tired of having NO good men to date?  THIS  is for you!

Hi, I'm Dr. Diana Kirschner. My team and I have helped thousands of successful single women, including judges, famous shrinks, CEOs, philanthropists, Directors, professors, and celebrities like Hoda Kotb from The Today Show to find a high-quality man who understands, appreciates and cherishes them, and I'm confident we can help YOU too!

I'm a PBS Love expert and psychologist who has appeared on Oprah, the Today Show and in an Amazon Prime show, Love in 90 Days based on my bestseller Love in 90 Days.  My work has been featured in The New York Times and The Wall Street Journal, ABC, People, and NPR.

I specialize in helping high-caliber women create feminine self-confidence, dating success, and passionate love matches.

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  1. Kay on February 9, 2010 at 11:10 am

    During the “inbetween” times of dating, there is a great book that is encouraging for the boomer gals.
    When You Grow Up and Get…Single. Fun, light, easy read. But-90 Days, so glad you’re here!

  2. Gudrun on March 3, 2010 at 2:51 pm

    I am a 50 year old female,living in Reykjavik,Iceland.I ordered the book,Find love in 90 days and loved it.Only the thing is,here we do not have so much on line dating,we do have one dating site but it is mostly used for …one night stand..since it is recommended to meet the guy only after few emails..I can not use dating sites from others country’s.I do envy you lady’s that can use the big dating sites.Also here in Iceland we do not have so much dating culture as in the USA.I know many,many single woman here whom are all having trouble getting asked out for a date.Maybe i should be the one to try this program out and pass it on to the Icelandic women…and do not know where to start.

  3. Dr. Diana Kirschner on March 8, 2010 at 2:50 pm

    Try to find activities that you would enjoy with lots of guys in them–like courses on leadership, business, sports, dancing, hiking,etc. Make sure you make eye contact and smile and chat with the guys. also, vary your routine to meet more people!!
    Wishing you love,

  4. Marvin Samul on June 27, 2010 at 8:18 am

    I have a hard time staying in a lasting relationship. It has finally occured to me I need dating tips and advice. Obviously I turned to the internet and found your site on google and I am glad i did. good information on here. Keep doing what you’re doing. I’ll bookmark and be back! On-line Dating Help for the Shy Man

  5. Kathy Klipfel on January 5, 2011 at 2:26 pm

    I am stunned at the bits and pieces I ignored before I read this post. Thanks for the first-class information.

  6. Katha on January 31, 2011 at 7:20 pm

    “Women, make sure you use a great headshot photo — men are very visual.”

    Whoah! Women are very visual too. I reject most men online because their photos are so bad. You need to tell men to have a great headshot photo, and a great bodyshot photo.

    I was interested in your work until “Dr” John Gray recommended it. Gray is very male chauvinistic and there are some great critiques of his work on the Internet. Check out “The Rebuttal from Uranus” and “Out of the Cave: Exploring Gray’s Anatomy.”

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