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How Not to Date for Widows Widow Repair

If you’re a widow, when is the best time to start dating again? Being a widow, where do you find potential dates? How do you handle new relationships if you’re a widow? Haha, I don’t know either. This is a compilation of anti-advice based on my own experience.

It was more than a year after Jason died, and I decided that I should try going on a date when I met someone new in Beaufort.

However, it wasn’t long before I had to be honest with myself. I wasn’t making any progress. I was actually documenting a handy checklist for the dating impaired: Five Ways for a Widow to Sabotage Dating.

1. Avoid Online Dating Services.

I did not sign myself up on eHarmony or Plenty of Fish. Those websites are for people who are looking for a serious relationship. You may even be matched with a widower who can empathize with your loss. I didn’t have enough common sense to do something so practical.

The problem is, men come out of the woodwork when you aren’t looking for them. Subconsciously, I recognized chance as a surefire way to sabotage any potential relationship. Let the chips fall where they may.

*Mark found me downtown while I was walking to the coffee shop. Of course I was dressed in jeans, boots and a shirt that had been slobbered on by a horse (what can I say? I was working)!

He had dark hair, tall, thin build and tattoo sleeves- not my type. But he was interesting to talk to, and I agreed to meet him for a date in Savannah. I gave my friend the address and told her to report him if I disappeared. I proceeded to pat myself on the back for accepting a date.

That was a healthy way to jump back into the dating pool… right?

2. Criticize the Person Who Asked You for a Date.

Resolve to (not) be understanding of your date if you want to sabotage the relationship. Journal about everything that’s wrong with him. Follow my examples below:

Mark is divorced for no better reason than that he and his wife grew apart. That makes no sense to me. I can understand people not being in love in the first place, but they got married three months after meeting each other.

Obviously, Mark develops attachments too fast.

He said he’s not the typical guy and that he has some understanding of what I’m going through. Yet he still asks me “hypothetically” if we should consider that we are dating. And “hypothetically” what would I do if he kissed me?

He also does not like Billy Currington. Really?

3. Play Dead if He Tries to Hold Your Hand

May 9, 2007 It’s difficult for both parties because I enjoy the company of other people, but I turned into a stiff board when he tried to hold my hand.

I told him that I cannot be affectionate because I miss my husband.

He says that I am nervous. But I am not nervous. I’m uptight.

I thought that if I hugged someone, I could find some comfort. I closed my eyes and tried to pretend I was hugging Jason, but that wouldn’t work.

So I regressed to thinking about how I didn’t want to be so close to him.

Misadventures of a Dating Widow Widow Repair

4. Convince Your Date that He Should Be with His Ex.

June 24, 2007 Mark still loves his ex-wife. He wrote about it on Myspace. I left a comment to say I know how he feels.

I wonder if he sits alone at his apartment in Savannah and wishes to be home with his wife. You know, I wonder if he ever wants his family back.

It would have to be better than living like a lonely bachelor. That’s probably why he kept asking me to come over. I want my life back too.

He seems to think that we were meant to meet even if it’s just to be friends. We both want the person we can’t have, even though it’s different circumstances.

I imagine that if Jason and I were in that situation, I would do anything to fix the relationship.

He’s basically a good guy. He denied loving his ex-wife, but I would rather see him get back together with her than date him myself.

I’m like the Cupid Widow! I’m doing this wrong…

5. Compare Him to the Person You Lost.

This one should be guaranteed to make them run for the hills, but it doesn’t happen quickly. In fact, I met Mark in April 2007 and heard from him sporadically until December.

I wrote this the last time I saw him:

This morning I took off my glasses at the carriage and sprayed bug repellent on my head. Squinting attractively, I noticed Mark walking over.

Surprise. He always shows up unexpectedly.

He announced a move to Pensacola, but he still thinks of me. He wants me to visit and call. He said he doesn’t know anyone else as sweet as me.

Mark is not at all charismatic like Jason. I just can’t see myself loving anyone, and I don’t know how long it will be before I do.

Is the problem with him or with me? Like I told Mark, I would be a great case study for a psychologist.

Nothing says more about my antipathy toward dating than my journal entries from 2007.

I don’t have anything to give or offer to a relationship. I don’t want to stick my oar in the water. Heck, with one oar, the boat only spins in circles, and it won’t go anywhere, not even for the one who is paddling.




*Name changed for privacy

First Dates

6 September 2014 0 Comments Category: The One

March 27, 2004

I called Jason from work, and he still sounded excited about going out. He called exactly at five like he said he would. We went to Applebee’s, where I decided to avoid ordering my favorite (hot wings) because I didn’t want to look like a mess in front of him. I got a salad, and of course he got the wings and a Crown and Coke. Not fair! Haha. He was telling me all about his job, but I can’t remember what he does because I was so distracted just being with him.

We walked on the Waterfront and then saw the movie Ladykillers with Tom Hanks (it was fantastic)! But the whole time I wondered if I was boring him, because he was constantly looking at his phone. When he dropped me off I got a hug, and he asked what I’m doing tomorrow. Then he told me to call him again. He never mentioned the dating thing, so I was very confused until he called at midnight! He wanted to see if I was okay and say he’s glad we saw each other at Keith’s.

I told him I was so glad he called. He said he had a really good time. So we are set to play some basketball tomorrow after work. That should be a blast! Alli said she doesn’t know if I should date him, but I should pray. She’s right.

March 28, 2004

Jason is a gem. He is sincere, chivalrous, likes kids, loves his friends, etc. We played basketball on Lady’s Island, and his cousin came with his girlfriend. I laughed so hard when they did a “play” then acted out a “rewind” at a faster speed. I wish I could have that on tape.

We took a break and talked seriously too. Jason wanted to know if I liked being with him and why. I tried to explain, you know, how I always liked him. He keeps saying that I’m so sweet. He even played the game so that no matter what, it wouldn’t end. He made up rules that I couldn’t make sense of, but he insisted they were legit. If he didn’t make a shot a certain way, he had to make five more before we could quit.

He called me around eleven and said he missed me when I left. He saw me looking like a hobo all covered in dirt and sweat, and he still called me and told me my eyes are pretty.

March 31, 2004

I never imagined life could turn itself around and become so happy. Jason finally made it to my house around 8 and met my parents. I laughed when Jason said he was worried that my dad would look like a biker, so he was relieved to meet someone not-so-intimidating. We played pool and watch a movie. Jason is a gentleman and so sweet even in competition. If we touched shoulders getting out of each other’s way, I literally got a shock. We played for about five hours, listening to country and some Brian McNight type songs. Our game really improved too! We plan on making a great team. He reached back and got my hand when he was on his way to the door.

After he left he called asking if I think we can date. He missed me already, and I miss him now. I wish we could see each other tomorrow. We have plans to golf, play tennis, pool hustle, paintball, go on trips, etc. We will be going to church together on Sunday morning and having dinner with his parents on Saturday night. I am so excited!! All thanks to God!


He used a series of phrases that I will never forget… a perfect shot was “Beautimous.” If you hit the ball into the pocket with enough force, he would exclaim proudly, “With authority!” He carried a black pool stick in a leather case and seemed embarrassed when he said he bought it at Walmart. My parents have a beautiful pool table, and every time the eight ball went into the pocket, he would swipe the rack from the wall and say, “One more game.” My mom called him Jason “One more game” Drew. He always racked the balls the same way- by numerical order and by color, and I have done it that way ever since. He rested the eight ball on top of the others, and when he shoved the rack forward, it fell into the vacant center spot.