Ultimate Widow Dating Guide

A picture of a couple on a coffee date

Hello ladies!  I have been dating for several years now and I’ve had this idea knocking around in my head that I should write a guide to let you all take advantage of the lessons I have learned through experience.  I am not a dating expert by any stretch of the imagination, but dating can be a scary experience if you’ve been out of the loop for a while, or decades like I had.  So here it is,  My Ultimate Widow Dating Guide.  



When To Start Dating

I have been a widow for 5 years.  Since January of 2016.  Four months later I started to date.

What???  So soon?  Too soon?

Some people thought so. 

But you know what?  The only person who counted in making that decision was me. 

Did I still love my husband?  Of course, I did.  I met him when I was 16 and was married to him for 48 years  Ups and downs, like all marriages. 

But guess what?  He was gone and I was not. I wanted to make new friends, I wanted to feel more alive and not just wait around until my life magically got better, or ended.  Did anyone else know what that felt like? 

No.  This is a very personal decision. 

Start dating when you are ready.

Was dating easy?  Nope, not at all.  This is why…

Why Dating As A Widow Is Hard

  • I had no idea what I was doing.  I was 68 years old, not the teenager I was the last time I dated.  Then I was in high school and everyone I knew was single.  The dating pool was enormous at that point. Now everyone I know is married, making the dating pool a tiny little puddle.

picture of a woman nervous about dating

  • Dating rules have surely changed in the last 50 years.  OMG.  I wondered what they were. 

I heard a rumor that men now expect sex by the third date.  That can’t be true, right?  I remember a really great date, a music venue, and dinner.  Afterward, my date announced that he deserved sex after that great date.  It was my third and last date with him.  I realized dating was going to be a shock to my system.


  • I tend to believe people.  Hmm…does that make me gullible?  Definitely, making me a prime target for a romance scammer.  I knew I had to guard my heart.


  • Are there any single men left?  Where in the world are they hiding?    Before you ask, I’d already been checking out the “normal” places like the grocery store and church.  Ladies of my age, listen up, all the men out there seem to be married.  So you have to dig a little deeper.  Finding a gentleman is a challenge.


  • Dating is risky.  Obviously, there is a physical risk.  I knew to protect myself from that.  I was more worried about the emotional risk, though.  My poor tender heart.  After losing my husband, I was concerned about exposing myself to another heartbreak.  Starting anything new is risky, but dating at that point in my life was really pushing me beyond my comfort zone.  This is what I decided…


If I could survive the heartbreak of losing my husband, I could be brave enough to take this risk.  I either take a risk or be safe in the same place forever. Wishin’ and hopin’ were not going to make it happen.


So I took the plunge and joined a dating site.  Now honestly, my kids were not happy about it and I completely understood.  They were still grieving their father and they worried that their poor mother would be taken advantage of.  But they had their own lives to live and I had to find my own way.

Perils of Dating

I did lots of research before joining a dating site.  I learned that most dating sites have both free and paid options.  What I discovered is that men who are serious about finding a relationship are willing to pay the money for the paid version.  If a dating site is totally free, skip it altogether.  That’s where you’ll find scammers, “players” and nutcases of all kinds.

What is a Scammer? This is the definition of a romance scammer according to the FBI:

Romance scams occur when a criminal adopts a fake online identity to gain a victim’s affection and trust. The scammer then uses the illusion of a romantic or close relationship to manipulate and/or steal from the victim.

Remember, these people have done their research carefully and have tailored their profiles to match yours.  This is called “catfishing.”  So cruel.  I came across a few of them.  Luckily I recognized their fakeness before they had a chance to ask me for money.  Some clues:

  • Their profiles are written in perfect English, but when they start to communicate with you, it seems a little bit off.  Close, but not perfect.
  • They oftentimes claim to be gemologists.  I don’t know why, do they think it sounds fancy??  I had at least 4 guys tell me they were gemologists.  Weird.
  • Their profile pictures may show them in full military regalia.  And they are doing duty in some far-off place.  Seriously, not born yesterday, buddy.
  • His profile picture is very handsome, and not only that, it looks familiar.  That’s because it is.  You’ve probably seen it on at least 5 other profiles.  Or on tv.

Most legitimate websites have anti-scam mechanisms and make members verify their pictures.  However, even after that, if someone seems sketchy, move on.

What is a Player? The Urban Dictionary definition of a player is:

Usually a boy (guy) makes you feel special. He makes you feel like you are the only girl in his life, when really you are just one in 100. They flirt with other people, not just you. He talks to you all day, then the next day they ignores you. They send you mixed messages, and you’re not sure whether he likes you or not? You can’t keep your mind off him, even though you know you’re nothing to him.

Yeah, OK, that must have been written by a guy.  If you want to know the real definition of a “player,” ask a woman. 

A player is a guy who acts as if he cares about you but what he really cares about is his own ego and his own pleasure (getting laid).  After he accomplishes his goal he moves on to his next conquest.

If he says “I think we should see other people,” believe him.  The relationship is over.  Move on.  He is dead to you.  Seriously, you don’t need him.  Find someone who has values that match your high values.

There is another category of men who aren’t necessarily players but let’s call them time-wasters.  If you have been dating a guy for a period of time and he is indefinite about the relationship, he probably has no desire to make it long-term.  And if he says these words:

“I’m not looking for anything serious right now,”  I don’t care what excuse he uses, believe him and get out!

What is a nutcase? Everybody’s idea of a “nutcase” is different, but if a guy is into stuff that you think is weird, move on.  Believe me, I met a lot of them.

Which Dating Site To Join

There are plenty of legitimate online dating websites to choose from out there.  Here are a few:

I ultimately decided on Match.com (I tried others too) because it’s been in business the longest amount of time and has the best reputation.  There, I found the profiles and pictures of the men quite adequate most of the time, and, as it’s a paid site, I found the guys were serious, not players.  Play around with the different sites and see which one fits your style.

A word about the pictures men choose for their profiles…please show me a nice picture of what you look like now.  This is what I don’t care to see:

  • Gym selfies and naked (or half-naked) pictures.  You’re proud of your physique.  Good for you. picture of a man on dating site flexing his muscles


  • Grumpy guys.  Are you looking for a grumpy woman?

picture of a grumpy man on dating site

  • Group pictures.  You’re in there somewhere.  

picture on a dating site of a group of happy men

  • Old pictures.  You were such a cute little boy! You looked good in your senior picture as well.  Do you still have teeth?

picture on a dating site of handsome boy

  • Pictures of your vehicle.  Nice, but where are you?

Picture on a dating site of a sports car

  • Pictures of your pets.  I’m looking for a man, not a dog.
a picture on a dating site of a cute dog
Came close with this one, though. So sweet!


  • Bathroom selfies.  This one really gets me.  You’re clearly sitting on the toilet in your old undershirt.

Man taking selfie in bathroom for a dating site profile picture

Men…if you want a date with a nice woman, go to the trouble to post a nice picture.  That goes for you too, ladies.


picture of a skeptical woman after looking at dating site profiles

The First Date

My first dates were pretty bad.  You’d think after all the research I’d done, I would have figured out how to find a nice gentleman fairly quickly.  Nope.  How can you expect to find the man you’re looking for if you don’t know what that is?  Figuring this out takes some time.  Take it.  Be patient.  The filters included in the websites do include some basics:

  • how far away are you willing to date
  • in what age range you’d like your date to fall
  • what height would you like your date to be (or not be)
  • what religion, if that matters to you
  • their smoking and drinking habits

I filled out my profile, filled in my parameters, and let it rip.  My matches were on their way.  Yay!  And this is what I got:

  • lots of “likes”
  • some “super likes”  Woohoo!
  • some “Hey!”s or “Hi there”s

So when I got an actual message from an actual man showing interest, I was pumped.  Coffee?  Sure. When I arrived at the coffee shop, the very nice gentleman met me at the door with his golf cap in hand.  So far, so good. 

At the table, we ordered our coffee and spent a few minutes talking golf.  After about 5 minutes he started to cry, explaining that after his stroke he no longer had control over his emotions.  OK.  

I am a nice person with sympathy for others.  But this was not a person I wanted to date.  Not wanting to lead him on, I told him right away that I didn’t think we were a good match.

He cried harder.  After that, there were a few days where he begged, making me feel horrible until I finally blocked him from the site.  You can do that.

My next several dates were better, but it was clear that I needed to be more selective.  I hated having to give the “you and I are not a good match” speech.  Even though I tried very hard to do it nicely.

I had some pleasant dates and also some negative ones.

Dates That Went Wrong

  • There was the guy who, after setting up the date and before meeting me, messaged me and told me what to wear.  What I was required to wear.
  • There was the man who set up a date at a very nice restaurant and then never showed up.  No apology.  Never heard from him again.  Actually, I did.  But he’d forgotten he’d already tried with me.
  • The guy who didn’t disclose his blindness until we met.
  • So many men looked nothing like their pictures and/or lied about their ages.
  • I was “ghosted” too.  That’s when a guy shows a lot of interest and then completely disappears.  That’s OK.  If there is no interest, there is no interest.  Of course, the more polite thing would be to just tell me.

I carried on.  There were many dates that went well. I had a good time. I met some new, interesting people with the potential for romance perhaps developing later, and others with whom I became good friends.  Dating can be discouraging and exhausting and you begin to wonder “Is there such a thing as a real connection these days?”  The answer is yes, but if you are in a smaller dating pool like I am (older woman) it might take a bit longer.  That does not mean that you should settle.  Never settle.

My Widow Dating Rules

  • Online dating is intimidating, but be brave and take the risk.  If you decide you aren’t ready, most dating sites will let you take a “pause.”  No money back, though.
  • Be selective.  I went on many dates only because I didn’t want to hurt a guy’s feelings.  Don’t do that.  His feelings will be hurt more in the end.
  • Never date a married man.  For me, this is a blatant moral issue.  But other than that, 99% of the time, dating a married man is a waste of time as you will always be NUMBER 2.  You will not meet his kids or his friends.  If he was serious, he’d already be divorced.
  • Honesty is critical so never lie.  So you’re a bit older.  Own it.  You look great.
  • There is no point in developing a relationship with someone who lives far, far away.   Unless you want a pen pal. Or a sexting partner.
  • If the conversation becomes sexual even before you meet, end it.  You already know what that guy wants.
  • Don’t let someone you haven’t met yet pick you up at your house.  In fact, don’t give him a clue where you live until you are sure of who he is.  Then you may let him be a gentleman and pick you up.
  • The same goes for phone numbers.  Use dating site messaging until after you are sure who he is.  Sure he wants your cell phone number so he can let you know if something comes up.  Uh, no.
  • Never leave for a date without a fully charged cell phone.  Also, let someone you trust know that you are going on a date and where.  Call her when you get home safely.
  • Do not lead a man on.  You are looking for a partner, not someone to fund your dinners out.  And if, by any chance, you are only looking for a night out, pay your own way.
  • If something feels the slightest bit off, move on.  Or go home if you are out.
  • You know all those things I mentioned that men shouldn’t do?  You shouldn’t do them either.  Keep your standards high.


It Sounds Too Perilous, Is Dating As A Widow Worth It?


My answer is an absolute yes.  Dating at any age is fraught with insecurities and emotions.  But you are special.  You have been through pain and survived.  So….

Take advantage of my experience and follow my ultimate dating guide for widows.

Use your common sense.

Love is risky but worth it.


I need to show that I’m a lone, fierce she-wolf.
 Selina Meyer (Julia Louis-Dreyfus) in “Veep”


As always, take care. You can do it!

For more information on dating after widowed, see these books available below:

    A picture of book Dating After Death Of Your SpouseA picture of the book, The Widow's Guide to Datingpicture of book The Ultimate Dating Guide For Widowers


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