Dating Over 40: Dating Dilemma #256 – Should I Wait or Email?

Dear Ronnie,

I have a dating dilemma that I could use your help with. I attended a speed-dating evening in August. When I received the “match” results, to my delight – the fellow I was MOST interested in had expressed interest in me!  A few days later, I received a very nice e-mail from him asking if I’d “like to continue the conversation” I said yes, gave him my number and mentioned I’d be away on vacation the next week (which was last week.) He said he’d try to reach me at the end of that week.

Well, SURPRISE I haven’t heard from him and now almost another week has gone by. I’m not sure what I should do. Should I wait to see if he contacts me? Should I assume “he’s just not that into me?” Should I drop him a brief, but friendly e-mail saying that I’m back from vacation and just wondering if he’d still like to get together?

One of my girlfriends said I should just be patient and wait. He does have 3 young kids and things may be really busy since school just started. Two other friends thought I should go ahead and e-mail before he forgets what I look like and because “life is short”  What would you advise in this situation?
                 –Lady in waiting

Dear Lady in Waiting,

Normally I prefer to have men do the reaching out. And he did that one time, but then hasn’t followed through. Who knows why – his reasons probably have nothing to do with you. 

The Situation Analysis
For all we know one of his kids got sick, he met someone else, or he’s working on getting his corporate taxes done – they’re due soon. It’s anyone guess.  I do feel that this is a sign – because you want a man who can follow through – who seeks you out and wants to date you.  On the other hand, people do get busy and then after not calling, sometimes a guy feels too embarrassed to reconnect.  Maybe he lost your number – oh no, sounds like we’re making excuses for him now – that’s not good.

The Advice
This fits the “What the heck?” category.  You liked him and hate to let this go.  I understand. What the heck? Send him an email. Go for it! The last thing you want is to wish you had just sent him an email.  Not a regret worth creating. 

So go ahead. Send him a  friendly email. You can either just say “Hi, how are you? I’m back from vacation.” Or if you can handle the possible rejection, suggest getting together to do one of the activities you have in common, without picking a specific time – just ask about over the next week.  There’s really no big downside to doing this.

The Fine Print
What I encourage women to AVOID is making the first move more than once because it will become a habit and ultimately you could waste a lot of time and heart on a guy who’s just curious or flattered by your pursuit, but not that interested. 

Sending a friendly nudge is not a bad thing to do, so do it right now after reading this. Then move on to think about something or someone else.  It’s a big world out there and there are plenty of fish.  Don’t get stuck on one lone sole when there’s a whole school swimming by.

Lots of Love from the Dating Coach

Single for too long, Ronnie wanted to find love. So, she made a few tweaks and then dated 30 men in 15 months to meet her adorable husband Paul. Discovering the keys to midlife dating, she founded It’s Never Too Late for Love to help other smart, successful women find love too! Her mission is to share her proven dating advice  and keen insights about men with women everywhere who are serious about finding love with the right man. Ronnie Ann Ryan, MBA, CCC is a Certified Coach who has helped 1,000’s of midlife women with her Love & Dating Coach services. She’s been featured on BBC’s 5 Live Radio, NBC, ABC, and Fox News, NPR, eHarmony,,, Connecticut Magazine among others around the world. An established author, you can find her 6 books on Amazon.

2 thoughts on “Dating Over 40: Dating Dilemma #256 – Should I Wait or Email?”

  1. Hi Roanna,
    Of course you could simply email him again. Say something funny or friendly, but most of all, keep it light-hearted. He is emailing and meeting lots of women, most of whom live in or near Austin.

    It’s hard when you see someone who appears to be perfect because you can get taken in by a profile. That’s not reality though. You have to meet a guy and date him to know what he is really like.

    Don’t fall in love with a profile or a couple of emails. Instead, use this as a spring board to move forward with your plans, not because of Mr. Austin, but because it’s the right thing for you to do. It’s much easier to meet and date people locally as you can imagine. Good luck!

  2. Hi, I have a dating question.
    I live in the Boston area but am seriously considering relocating to Austin. So I reviewed profiles on a dating web site for Austin, and found and amazing man, who I feel is perfect for me. I have reviewed and heard from numerous men, but feel this man might be my soul mate, maybe that sounds silly. So naturally I am nervous and excited.
    I emailed him, and he said some really sweet things to me and said he was looking forward to knowing me more. I replied and gave him a compliment.
    Now I have not heard from him. What should I do?
    I have not heard back from him.


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