Dear Lisa, My Older Boyfriend Doesn’t Trust Me

 

Dear LisaDear Lisa,

I’ve had men write me online but I just don’t know how to answer them.  Any suggestions? Margie

 

Margie,

I like to look at online dating as if it’s a virtual cocktail party.  How would you act at a party?  You’d be fun, flirty and cute.

Your flow of emails are the same as cocktail party conversation – light and fun.

To do this, take a few moments to collect your thoughts before answering a man’s letter.

Keep your answers short and be sure to ask a fun question he can respond to.

You’ll find if questions aren’t asked, email flow can end.

If he starts asking serious questions in his emails, then suggest taking your conversation to the phone.

See this as the fun/flirty phase of opening up a conversation to see whether you want to talk or meet a new man.

 

Dear Lisa,

I’ve dated off and on since my divorce.

About three years ago, I met a man named Steve.

After a couple of dates with a little bit of kissing and some minor touchy feely playing around, we realized we were not meant to be in a romantic relationship with each other.

Yet we enjoyed our friendship and began meeting for lunch once or twice a month.

When it comes to paying, we always take turns or we split the bill.

We both enjoy this friendship but have no desire for any more than that.

About six months ago, I began dating an older man.  I am 57 and he’s 68.

He thinks this friendship is wrong and I’m being disrespectful of him by doing this.

He believes men and women heading into a serious relationship should not be friends with a member of the opposite sex they once dated even if it was brief.

I’m having a hard time with this since my friend and I have known each other longer then this man and I have.

I don’t understand why this is such a big deal.

I’m not romantically interested in Steve at all. I’m not sure what to do about this.  I’d love to get your insights. Livia

 

Livia,

I’ve known many men and women including myself who have stayed friends with people they briefly dated.

Often a romantic relationship won’t work but a plutonic one does quite well.

It sounds like your boyfriend might have some trust issues.

There’s always the possibility a woman in his past cheated on him and he’s projecting his distrust upon you out of fear you’ll do the same thing.

Also, your current boyfriend is a member of the Silent Generation, the men and women born prior to Baby Boomers.

What might help you is to understand this man comes from a generation where honor, respect and doing the right thing are part of his core.

This man would likely lay down his life for you.

Think of men who, in Medieval times, would have dueled for your heart, believing may the best man win.

To your boyfriend, Steve is being disrespectful of his territory, which he sees you as a part of.

Boomers view life differently than many from the generation before them.  They grew up with free love and give peace a chance.

This is the reason for the conflict you have in your relationship.

So where do you go?

If your relationship with this man is something you want to continue, you will probably have to give up your relationship with Steve.

I’m not saying its right, but it’s likely the only way you’ll have peace with your boyfriend. It sounds like there’s no room for compromise here.

Or you can find a man who may have female friends of his own and will be fine with your friendship with Steve.

Your heart is a great guidance system.

Check in and see what feels best to you to get your answer.

Believing in You!

Lisa

P.S. Whenever you are ready, here are four ways I can help you find love after 50

#1: Get a copy of my book The Winning Dating Formula on Amazon



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#2: Join the Finding Love after 50 Facebook group

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#3: Work with me 1-on-1 or in my Group Program

I would love to learn more about your dating journey, understand where you might be stuck, and give you a personalized step-by-step blueprint to attract the right man. And maybe even talk about how we can work together.

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Copyright© 2024 Lisa Copeland. All rights reserved.

3 Comments
  1. Hi Lisa, I enjoyed reading your post and it inspired a lot of thought on the subject.

    If your post was first written in August 2015 the “older guy” was probably born in 1947. He is a boomer. He’s not a member of the previous cohort, the silent generation, although his parents might have been.

    He’s a leading edge boomer and there are also boomers slightly older than he.

    • Hi Leigh…so glad you are enjoying the posts here. You are right about the age but, this women did give the age….I didn’t post it. It was 1944. Thanks for bringing this to our attention! Lisa

  2. I think this is really a deeper issue than just this one. He is attempting to decide for you who you can and cannot be friends with. I would take a step back and look closely to see if its really just this one issue or is it a part of a larger control issue. I know you only mentioned the one male friend, but are there other areas that you’ve just not noticed? How to wear your hair? How to dress? Time spent with girlfriends?
    As for me, I personally would never let anyone come between me and my friends… I’m still friends with two guys I dated in college from almost 30 years ago. But it is really a choice you have to make.

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