Welcome to Our Weekly Magazine

Become the best version of yourself Sign-up for our weekly magazine.

Become the best version of yourself today.

We send a weekly roundup of our best work and highlight standout community members. It's free, and you can always leave if it's not your jam.

Dear Gail: Tired of Dating Sites? Hunt Down an ‘Ex’

Is it ever a good time to reconsider dating an ex? And how late in a relationship is too late for “full disclosure”? Comedian Gail Forrest advises.

Tired of Dating Sites? Hunt Down an ‘Ex’

Dear Gail:
I am in my late sixties, heading full speed toward seventy. Being single and having tried numerous dating sites over the past few years I am still shit out of luck. It was like fishing in a pond with 2 fish. Is it time to reconsider exes both husbands and boyfriends? See if anyone is still available? At least I know their upside and downside and maybe they’ve changed?


Dear Margaret:
Before you go on this man hunt be prepared for sagging stomachs, hair and hearing loss, and possible shrinkage. I have seen it all and it’s not hot.  

SPOILER ALERT! Don’t be surprised to find “exes” in the obits.

Do not waste time looking for the “never married” ex-boyfriend as he is a life time commitment phobe. Next! Vegas bookies say a widowed “ex” is your best bet. If you have one of those take a plane, train, or automobile to find him ASAP as they go fast.

You could face the same disaster I did. Many of my old boyfriends married the next woman after me. Was I chopped liver or cursed? I consulted a therapist, astrologist, and fortune cookie from the Szechuan Palace. The cookie was enigmatic – “The fortune you seek is in another cookie.”  I ate a lot of hot and sour soup trying to find that elusive cookie. The search was futile and fattening.

Even if you re-connect they will still be the “ex” you left. My advice: look for new hunting grounds. And under any circumstance get a Golden Retriever.  

Club Fed — A Destination Wedding 

Dear Gail,
I’m in my late fifties and met a man online I have been dating for three years. The relationship has become serious and we are talking marriage. Last week he and I were at a romantic French restaurant and I’m getting ready for the proposal, when he hits me with, “Kelly, I love you but it’s time for a full confession before we go further. I went to prison eight years ago for insider trading.”

Don’t you think that he should have told me this on our 1st, 2nd or 3rd date?? I am in a state of shock and disillusionment about his keeping this secret.

What should I do? And should dating sites do background checks on their members?

Any advice welcome, thanks so much,
Kelly T.

Dear Kelly:
I am not hearing wedding bells. What happened to full disclosure three years ago? This is not petty theft but full on prison time regardless of its white collar crime status. Now you’re in love and expecting a ring only to get a confession. To hell with romance. Let’s see some prison pics. It’s possible he made some nice pot holders, lanyard keychains, or license plates he could give you on your first anniversary.

The prospective groom is also guilty of the “sin” of omission which begs… what else has he omitted? I doubt there’s a body in the freezer but you might want to check for stacks of hundreds before you leave.

I would love dating sites to find a way to background check members. My dating motto is: presume someone is a serial killer until proven otherwise. I Google search every prospective date, cross reference with name and address sites and search Google pics.   Always remember Ted Bundy.  

Need advice? Gail wants to hear from you. Send your letters, questions, and quandaries to: newsletter@weareageist.com

See medical disclaimer below. ↓



Please enter your comment!
Please enter your name here

The ideas expressed here are solely the opinions of the author and are not researched or verified by AGEIST LLC, or anyone associated with AGEIST LLC. This material should not be construed as medical advice or recommendation, it is for informational use only. We encourage all readers to discuss with your qualified practitioners the relevance of the application of any of these ideas to your life. The recommendations contained herein are not intended to diagnose, treat, cure or prevent any disease. You should always consult your physician or other qualified health provider before starting any new treatment or stopping any treatment that has been prescribed for you by your physician or other qualified health provider. Please call your doctor or 911 immediately if you think you may have a medical or psychiatric emergency.

David Stewart
David is the founder and face of AGEIST. He is an expert on, and a passionate champion of the emerging global over-50 lifestyle. A dynamic speaker, he is available for panels, keynotes and informational talks at david@agei.st.


Recommended Articles


LATEST Profiles

Latest in Health Science