Five Ways for a Widow to Sabotage Dating


Shared by Bonnie Drew.

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

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