Dating Over 40: Why Can’t We Be Friends First?

FriendsToday, I met with one of the first men I ever coached. It was great to see him, catch up and of course talk about dating. After 8 years, he looked exactly the same which is pretty darn good for late 50’s.

Barry was in  a five year relationship that ended this past fall. He’s feeling like it’s time to get back out there and start dating again. He meets quite a few women in his line of work, but Barry is not what you’d call a smooth operator. He is a very nice guy, smart, creative, lives a holistic lifestyle and enjoys the arts.

Recently, he met a woman, Barb, who he was attracted to at an event with friends and they chatted for a while. But, Barry hesitated. He didn’t ask for her number. Instead, he invited her to the next event – what I’d call a low risk, “soft” invitation. A friendly approach.

Barb showed up at the event and hung around until everyone else left. Barry asked if she’d like to get a cup of coffee and Barb said yes. According to Barry, they had a fun conversation and  emailed frequently over the next two weeks. Finally, Barry asked her for another coffee. Unfortunately, Barb no longer seemed eager to get together, giving him the brush-off.

Barry told me he surprised and felt rejected. As The Over 40  Dating Coach, here’s what I explained to him:

1. His unwillingness to be direct and ask Barb out at the event shows his ambivalence about dating. Waiting two weeks to ask for just another coffee was another example. Maybe he’s not quite ready.
2. Barry doesn’t want to play the game again and is risk averse. We all know that’s not going to work. No way around the dating game.
3. He asked, “Why can’t we be friends first and see what happens?” This may work on rare a occasion, but not as a planned dating strategy! Once a man is “friend material”, it’s hard to get back into the romance spot.

Barry is not ready to date. So he has created a series of obstacles hoping to safeguard his heart. His ambivalence on taking a risk and going after a woman who he’s attracted to, have resulted in more than one woman having a change of heart. He sees this as their own indecisiveness, but I see it as a reflection of his lack of readiness and commitment to the process. 

Dating is about risk taking. You cannot date if you are not capable of risk or vulnerability.

I gave Barry the key to success for him once  he’s ready. In the holistic and artsy community, he could be like gold. A hot commodity in a world where the few men are either skilled players or nice guys women see only as friends.

Barry needs to step up to the plate and use his leadership abilities which he most definitely uses in other areas of his life.

Women want a man who knows what he wants and takes the initiative. If he doesn’t start using more masculine energy, he’d surely find dominant women who want to be in charge. He’s been there, done that and doesn’t want to go there again. The only solution is to become a “hunter” as Patti Stanger, the Millionaire Matchmaker would say.

As I was leaving Starbucks, I knew Barry had a lot to think about. He is completely capable of making the right moves. He a very loyal, decent looking man, well kept, interesting, talented and smart. He prefers being in a relationship than the single life. Personally, I’m rooting for him. When he’s ready, he will step up to the plate, take the initiative, pursue women and find the right one for him.

Photo Credit: Michaelallroy

Single for too long, Ronnie wanted to find love. She put her skills from personal development and her spiritual path to work, dating 30 men in 15 months to meet her adorable husband Paul. Discovering the keys to manifesting and midlife dating, she founded It’s Never Too Late to help smart, successful women find love or live an empowered and magical life. Ronnie Ann Ryan, MBA, CCC, is a Certified Coach who has helped 1,000s of midlife women with her Love & Magical Life Coach services. She’s the host of the Breathe Love & Magic podcast and has been featured on NBC, ABC, & Fox News, NPR, BBC, eHarmony,, and Connecticut Magazine among others. Also, Ronnie is the author of 6 books which are available on Amazon.

2 thoughts on “Dating Over 40: Why Can’t We Be Friends First?”

  1. Amanda – praise to you for doing right by yourself! Double “atta girls” for not slipping into “friends with benefits.” That could happen so easliy thinking you are hanging in until he’s “ready.” Sounds like you were immediately rewarded for this brave choice with another man!

    Taking the high road can be a challenge, but you will be the one who benefits.Good for you!

    PS – Steer clear of men who haven’t been divorced at least one year. They are almost never “ready” and need time to heal.

  2. Just wanted to share my “lets me friends” story……..

    A few weeks ago, I met a man who I really thought was going to be the one. I will save all the details but lets just go with that fact that this man had everything that I was looking for, more AND we got on like a house on fire….

    He had just come out of a 22 year marriage, wanted to find himself and date other women ( he had only dated his childhood sweetheart at 17 and married her ) …. all stuff that I understood.

    We both obviously had a great connection and one that I recognised instantly as I have been out in the dating world and knew that we may be able to have a good relationship…

    He obviously needs more time and asked if we could be friends and see what would happen in the future.

    I got it that I didnt rock his world enough or a man wouldnt let me go that easily…

    After learning all about how to play the dating game and how to attract true soul love , I had to practise my beliefs and tell him that I wasnt interested in friendship and that if after the 6months he needed to sort himself out, I was still single ( im pretty sure I wont be ) to give me a call.

    It took alot for me to do this, but it not a friend that I am after and I had to respect where he was in his love journey.


    PS The day I said goodbye to him, I met another man who is really making a huge effort to get to know me and create romance and may well be the next beau in my life and perhaps The One….


Leave a Comment