Dating Advice: Should I Stay or Should I Go?

Posted by in breaking up with grace, dating a dangerous man, love after 40 | 0 comments

should i stay or should i goHi Sandy,

I read your article about narcissists and it seems like you know quite a bit about what they are like to be with.  I’ve been seeing a man for almost 8 months, and in the beginning I felt like he was the one.  I’ll tell you I’ve been down a long road of hard relationships and dated so many jerks that I thought I had finally found the right guy.  He’s so sweet, thoughtful, kind, tidy even!  However, as time passes we never get any closer.  I feel like I know as much about him now as I did in the beginning.  He never asks me to meet his friends, and has dodged meeting mine for a very long time.  When he finally showed up for what he knew was an important night for me, he only stayed for a couple hours, and never really talked to anyone (my friends tried!)  Just when we would have finally had some time together over the xmas holidays he took a voluntary leave away for a month to work.  He says nice things to me but the feeling I get is that he could take or leave me at any given moment.  He goes on about his friends but I don’t think they even know about me.  And when I ask him to meet my family he always says “we’ll figure it out”.  I’m heartbroken at the thought of having to end it, but I also feel lonely in this relationship.  I’ve told him how I feel about him, and more so I show it.  He will never make any real emotional statements about me.  The last time I asked him where our relationship stands he said (and I quote) “You’re a real Dreamboat, but let’s talk about this later”. Then, when later comes and I try to bring it up, he completely changes the subject.

I guess my question is…is it worth talking to him about how he REALLY feels about me and giving him the chance to truly commit, or is that like talking to a brick wall? Also, if I do have to end it is it best to do it before he comes back and we fall into the same patterns? Should I stay or should I go??

Thanks for any insight,


Dear Ally,

As I read your email, two words popped into my head – self-esteem. I want you to love yourself enough that you never again need to ask, ‘should I stay or should I go’, especially if you’re dating a man who treats you like crap.

Saying that you’re a ‘dreamboat’ means nothing without the follow-through. He doesn’t open up to you, he doesn’t show affection in the same way that you do, and he hasn’t met your friends or introduced you to his. He is not there to support you. What exactly are you getting out of this relationship?

Crumbs. He tosses a few crumbs, and then you give and give and give. You end up feeling unloved, and you wonder why he doesn’t reciprocate.

Should I stay or should I go?

Walk away from this guy. Don’t wait until he comes back and you ‘fall into the same patterns.’ You have enough evidence that he is NOT the one, don’t you?

You might find this article helpful in breaking up with your guy.

Once you’ve healed from this pattern of dating men who don’t treat you with the love you deserve, start dating again. But this time, every time you’re on a date, ask yourself these questions:

  1. Am I having fun?
  2. Do I feel safe?
  3. Is the relationship escalating?

If the answer to all three is ‘yes’, continue to date. If not, cut him loose.

Your self-esteem is so important. How you feel about yourself is directly related to how a man will treat you. Love yourself more, and you’ll inspire respect and love.

I wish you the best of luck,  Ally. Don’t tolerate crumbs when you can have your cake and eat it, too!



For a copy of my FREE report, “The Top Three Mistakes Midlife Daters Make (and how to turn them around to find love now)” please click here.

‘Like’ my Facebook page for exciting posts on dating and relationships & links to my weekly radio show.

Want to experience private group coaching at a fraction of the cost? Check out the Last First Date Inner Circle! Monthly topic-based Q & A calls about dating over 40, a private forum for women to connect and share their experiences and much more, all at a very low price. Check it out here.


Leave a Comment

Your email address will not be published. Required fields are marked *

AlphaOmega Captcha Classica  –  Enter Security Code

This site uses Akismet to reduce spam. Learn how your comment data is processed.