A Few Tips For Valentine’s Day Online Dating

By Ira H. Silverman

I think online dating should work like buying a car. You want to talk to the previous owners, then automatically receive the Manfax instead of a Carfax.

For a major part of my life, Groundhog Day was my least favorite day on the calendar. I knew that if the groundhog saw his shadow on the morning of February 2, we’d face six more weeks of winter. That’s devastating to a guy like me, who loves the outdoor life, playing golf and other sports, and working in my garden as early in the year as possible.

But in 1993, my attitude towards Groundhog Day changed and another date in February jumped to the top of my annual most-upsetting dates list. That year, the seminal film “Groundhog Day” came out and all of a sudden February 2 became funny, hopeful and even a little romantic.

February 14, Valentine’s Day, took its place as my least favorite. If not having a date on New Year’s Eve can make you feel disappointed and depressed, not having formal plans for Valentine’s Day can make you feel lonely and a little like a failure. To get beyond those feelings, I take a creative approach.

Well in advance of Cupid’s holiday, I put myself to work and log on to an online dating site or maybe two or three. And I have figured out a pretty good system for approaching the often daunting task of find someone compatible.

For all the AARP-aged singles who might want to use an Internet dating site to land a Valentine’s Day date, let me share some tips that should help.




You need to prepare. In our previous post on online dating, we discussed the types of Internet dating sites to join, made recommendations for posting your photos and offered suggestions about how to write your essay and answer the probing and important questions.

You can find that post here:

For now, let’s go past those details. First you need to determine your “musts” and your “deal breakers.”

Don’t consider this shallow. Setting up criteria and acknowledging that you have certain requirements shows your honesty with yourself and others. My main considerations in deciding if I want to contact someone include how far away she lives from me. I have a 20-mile limit.

The first thing my eyes go to are the town or city where the woman lives. If she lives anywhere that requires me to take a bridge, a tunnel or ride on the Long Island Railroad, she’s not for me.

1. Her age. I prefer women three to ten years younger.

2. I need to feel an immediate attraction to her pictures.

3. I examine her likes and dislikes. If she hates cats or is allergic to them, she’s out. I have 3 cats.

4. If she smokes or does drugs, I don’t want to date her.

I consider her level of education and the spelling, grammar and punctuation she uses in her correspondence.

Some people take the options further and consider race, religion, body type, and marital status. Others won’t date a recently separated person or someone who never married.

Obviously we don’t have right and wrong choices here. It all depends upon your personal preferences.



OK, here we go! You now have a great profile page up in one or more places in cyberspace and a portrait in your mind of the type of man/woman you would like to meet. Don’t get intimidated when you log on to a site and begin to look at the matches.

You will immediately see photos of dozens and dozens of your potential dream dates based on the distance and age requirements you chose. I think most people our age can sense from reading a profile and answers to questions what someone is like. Is he or she easy-going or high maintenance, down to earth or egotistical, affectionate or standoffish, friendly or reserved, flexible or hidebound? Is his or her glass half empty or half full? That’s all pretty important. If they seem off to you, avoid them.


The Approach

You’ve found the right person and now you need to write to them. Hard and fast rules for your email don’t exist and we don’t have a template for how you should approach them or what you should say.

It turns me off when someone sends me an email that says “Hi” or “How are you doing today?” Both seem impersonal and indicate that not much thought went into her effort to try to catch my attention.

I use a strategy to show that I noticed things about a woman. I mention things that appeal to me about her, like her smile, the nice way she writes and perhaps her attractiveness in photos.

Next, I point out activities, interests and qualities that we both like and that we can do together. My favorites include outdoor sports, dancing, playing board games, dining out, walking on the beach at sunset, exploring Manhattan and doing volunteer work.

I usually wrap it up giving my first name and I suggest that we talk on the phone or meet for coffee. I hope the woman will respond to the message.

Tip 4


Before hitting “Send,” I strongly recommend that you go back and proofread your work carefully. Remember, you only have one opportunity to make a good first impression, and these initial messages give you the chance to excel and not fail in a potential date’s eyes.

Jordan Peters once quipped: “Valentine’s Day is just a nicer way of saying ‘National Feel Bad if You’re Single Day.’” We all know we can survive yet another Valentine’s Day without flowers, candy, jewelry and dinner in a fancy restaurant. But still.

If you start now, Internet dating options like POF, OK Cupid, Match.com, E-Harmony, Our Time or Tinder can make February 14 a lot less lonely.

Good luck! And let me know what happens.



Ira H. SilvermanIra H. Silverman, in the public relations field for more than 35 years, is known as “The Connector” among his business associates, family and friends. He uses strategies, techniques, research acumen, investigation skills and a lifelong network of contacts to bring together people and organizations who have problems, public relations and marketing needs and challenges. He cuts through red tape, open doors and gets people to say, “Yes.”