If He Doesn’t Make You Feel Special It’s Time to Move On

Ever found yourself wondering “Is he into me?” or “Should I move on?” Check out this email exchange I recently shared with a blog reader.

Dear Bobbi,

Thank you.  Your dating tips are helpful and have helped me change my point of view.

Before reading your blog, I’d been doing most of what you’ve suggested, without much confidence.

I’m 50 and have been online dating with some success at meeting good, intelligent, and interesting guys.

I finally met someone (who is a couple years) older than me, who I would have never chosen. When we met in person he was attractive, kind and interesting, after contacting me first. I replied.

Of all of the men I met, he made an incredible first impression and then things when downhill from there.  But, I like him and decided to give him a few more chances. Another chance to cancel at the last minute, stand me up, never call or seem busy if I called. I was trying to break an old habit of giving up too soon.

After one more postponed date, I was really disappointed  and emailed him that I wasn’t sure he was interested. Now I am split between thinking it was a mistake and the right thing to do. Of course I haven’t heard from him. I hoped it would lead to a conversation or reply.  But he just disappeared.

I thought it was a mistake because I finally felt grounded, ok to be myself, and calm in a relationship. I ignored the ups and downs hoping it would change and then realized it probably would not.

At this moment, I am disappointed, sad and miss him.  My interest in continuing my search is low. However, your blog tells me that I made the right decision. (Unless you can find a loophole, or ray of hope.)

I’m more interested in changing my point of view again.  There are attractive, mature, intelligent, affectionate, available men in their early 50s out there! I just have to take a deep breath and keep looking.

Best wishes to you.

“New York”


Dear Ms. New York,

I see a huge ray of hope: YOU! I see a courageous, smart and loving woman making decisions that will ultimately lead to achieving her most important goal. Dating over 40 is not always easy, and you seem to be managing it with a pretty good balance of head and heart.

What you described is somewhat common for women who are trying to break their pattern of being overly critical of men: they sway to the complete other direction and accept too much!

It sounds to me like you were being “pinged,” Ms. New York. He started off being Mr. Smooth, got your attention, and then the rest of the so-called relationship was on his terms. When he wanted to see or talk to you…he did. When he didn’t, he didn’t.

This is not a man who is treating you like you are special. He was not trying to win you over in any way. And he was not going to change. He just didn’t see you as a serious match. YES…you made the right decision!

The only thing I hope you do differently next time is realize this earlier and feel confidence in your decision. He wasn’t someone you could count on or who let you feel good about yourself. Maybe in moments, but I’m guessing that overall you felt a lot of self-doubt and disappointment.

After a man stands you up or breaks a commitment a second time, I say move on. That is, if you want a man in your life that is trustworthy and well-mannered. (Which I’m sure you do.)

I know it feels crappy to have your hopes dashed, but I’ll ask you what I ask so many other women in your position: was he really such a great guy, or were you in love with the idea of being in love and thinking you finally found The One?

Kudos for having the courage to be yourself with him and for calling him out on his unacceptable behavior. Also, congratulations for consciously choosing to maintain hope…even through the disappointment.

You are obviously a smart, thoughtful woman who is serious about finding a loving, committed partner. Continue to be clear on your needs and boundaries, and stick to your must-haves. (Like being treated with respect and honesty!)

You are now one step closer to your heart’s desire.

With love, support and admiration,


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