While out for dinner with a girlfriend, she informed me I had a piece of spinach stuck in my teeth.
I was glad she told me as I was headed to a meeting after dinner and a matchmaker with spinach on her teeth could have been a bit embarrassing.  For the most part, friends and family tend to let each other know if they have toilet paper on their shoe or if their zipper is down. But telling complete strangers can be a bit more awkward.
I did a poll on this scenario and it turns out that, for the most part, people actually do tell strangers their shirt is on backwards or their undies are showing — and strangers absolutely appreciate being told.
Now that we understand it is helpful to let people know of these tricky situations, the real challenge is determining whether people should give constructive criticism to their date if they decide there is something specific being done that may lead to dissolution of the relationship.
I have had this conundrum happen, in which a man or woman contacts me to let me know they have been on a few dates with a person. While they say they truly feel the other person is a genuine, thoughtful, great human, they tell me specifically why they are ending the dating process.
Obviously, if the reason is based on a shallow physical concern, sparing hurt feelings is definitely the way to go. However, if the reason is based on something the person can work on, I think it would be helpful to delicately inform them. In fact, by doing so, you could be helping them on their journey forward and your information could be the turning point that brings them to the next best thing. That would be an incredible gift to offer.
I have had people tell me that the man/woman they were seeing was a little sad, a bit forlorn, spoke too often of their ex or would not stop complaining about their boss.
If you were to inform the person gently and diplomatically about such peeves, and delivered it constructively, it could certainly be valuable information for this candidate.  Much like a company does an exit interview with an employee leaving their job, it give you an opportunity to make gentle suggestions for them as they move forward in their search.
By doing that, you could end up having a profound effect on the person; you could be their compass with the best direction they need to find true happiness.
Oh, and let them know if they have mustard on their chin.
If you are a single, happy person between the ages of 25 and 105, you should contact me by email at holmes@wheretheheartis.ca.