Dating at Midlife/Dating or Friends?


QUESTION: I met this amazing man through my daughter but I only wanted to be friends. Just wasn't ready to open up my heart. Well for 9 months we been going out to dinner off and on but last 2 months it has been almost every night. I tried to avoid  having feelings for him but now I really do like him. Here is the thing. He has a female roommate  which didn't bother me but for some reason I ask if she was an ex girlfriend and he said yes. That bothered me. Why didn't he disclose this info to me?
I don't know where I' stand with him , are we just friends ? Are we in an exclusive relationship ? I didn't know so I ask him. This is what he said. If exclusive is the sex side of it then yes he does. But he goes out to dinner with female friends and a few of them are ex girlfriends. I'm not okay with this at all.   He does want to see where this relationship goes but  not until I attend a life enrichment bootcamp. But until then he will decide how much further he will go. Yes I cross that line by sleeping with him   I figured it's been 9 months. But now I have regrets.  Is it normal for a man or anyone have their ex live with them or still see ex gf ? How could any female be okay with this ?

ANSWER: Hi Cheryl,

May I ask, how old are you and the gentleman?

I know of a number of now-married couples who originally started as friends, and much like the two of you, those professional and smart singles regularly went out to dinner as friends, keeping it platonic.

His situation really is quite intriguing.  There are those divorced couples who had to remain co-habitating but moving to separate bedrooms when the economy plummeted and the housing market was so dreadful. They didn't want to sell their houses quite yet.

But his scenario is fairly unique.  His roommating with an ex-girlfriend is a tad odd, but not unheard of.  How long were they a couple?  A few weeks?  Or was it about a one year romance or longer? Why did they break up.

His going out to dinner with other women friends is fine, basically.  And then there's the added layer of some are ex girlfriends.

He either just really loves women and their company, ending his romantic entanglements with no hard feelings.  Or he has a bit of a harem syndrome.  He might be holding onto their friendships with just that little 2% factor of hope of, "Yah never know," for the romantic flames rekindling.  Or he hangs onto them actively remaining friends, not just now in their extended social circle attending group parties together, in a way pre-empting new men from coming more fully into their lives.  For most women, it is harder on us emotionally to remain friends at the level of going out one-on-one with an ex-boyfriend.  Our heart emotions remain connected to him.

Start pushing back.  It's not that you need to issue any ultimatums.  Couples as they form into a committed life together in marriage just shift their lives to where all those old exs either move into the extended social circle or periodic walk buddies together, the odd escort for those few occasions each year when he has a theater ticket to something you really do not want to attend.  But they move into the outer social sphere, not regular one-on-one tête-à-têtes.

I'm sure it's how your phrasing it, not how he expressed it.  He is still unsure of things with you?  It's been 9 months and you two have become physically intimate? By then, most men know for sure and are wired to pursue and make you his, often with an invitation to move into his house with the promise of marriage within another year or two.

What is this "life enrichment bootcamp?" Is that something through your Church or Synagog? A personal development seminar?  Those can be great.  But usually, you know the person's heart and soul already after 9 mths.  

Reclaim your personal power.  You slept with him for you to test those waters with him.  Now ask for what you want.  A committed relationship leading to marriage with him.  Or if not, then return to a platonic friendship and see much less of him.  

If what you want is a relationship in marriage, is he offering that to you?

I hope this helps your dating coaching.

Los Angeles Dating Coach for Women After 40

If you want to know how and where to meet men over 40, stop by my website and sign up with your name and email to receive the gift ecourse on the home page. Don't settle for less than the relationship you want.

---------- FOLLOW-UP ----------

QUESTION: April , I am 50 years old and my friend is 46. He never been married or had any children. The roommate is in his home and I'm not sure how she ended up there. I think their relationship was long time ago and he help raise her kids. I'm bothers that he didn't share this with me. And I think it's strange he is there whn she is engaged to someone else.  The Bootcamp is a semiar that gives you tools to leave the baggage , hurt , resentments behind. He is a coach or trainer. Yes I would like to hope this would lead to something more. He was persuing me before I agreed to even. Dinner.  I don't think him taking old gf out is okay. What if I went out with an ex ? Well I have none since I been married forever.
I started asking questions to him and I'm not liking the answers.
My first one was , where do you see this going ? His answer was , I'll answer after you attend Bootcamp. I am going but not for him but for myself. I think he likes the women thing ! He is an amazing man he really is. I just wish I did not start having feelings like I do.
Maybe I should back off and see what happens.

Hi Cheryl,

My apologies for the reply delay.  I didn't get a notification of your response until I logged in myself directly and looked at pending questions.

I think your gut feeling is right on target.

His roommate situation is not a shared apartment, it's his own home and she lives there.  It's going to be awkward all over the place.

The Bootcamp seminar sounds like it might be good for relationship skill building.  However, the way he is presenting it as a hurdle for you is manipulative and makes it seem cultish when that might not be the case from the organizing association.  

He has known you quite a long time.  If he is not in love on his own, it's relatively unlikely he will be later on.  The Bootcamp could very well be a good learning experience, but they way he throws it up as a requirement before he verbally commits himself to at least being interested in marriage is wimpy and manipulative.

Push back and don't allow him to have a Fri or Sat night date with you for now.  And turn your attentions to looking for a man who wants to be with you and not 15 other women also.  You might be pleasantly surprised to find true love once you focus elsewhere.  He might be very interesting, but if he doesn't cherish you and aim to make you his, he's being slippery and weaving a fantasy of hopeless hope with you.

You own idea to push back sounds like the best thing for you to do, indeed.

Happy Dating and Relationships,

April Braswell

Dating at Midlife

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April Braswell - Dating Expert


Can certainly address the romantic questions from Boomers looking to date again after divorce or the death of their spouse. Address how dating and courtship principles remain the same, however many of the tactics are different now. How to use social media and online dating sites well which reflect your age and style, not that of your grandchildren.


As seen in Dating for Dummies, 3rd edition. I'm an internationally recognized Dating and Relationship expert, frequently on Radio and serve as "In Touch Weekly"'s go to relationship expert for questions regarding celebrity couple relationships. Additionally recognized for specifically serving the different romantic needs of the Baby Boomer generation, having contributed to such media as Gateway Media, Woman's World, and The Boston Globe.

As seen in Dating for Dummies, 3rd edition.

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