Dating in Columbus: A Series: Episode 11: Date With a Widow (Part 2)

So, the beginning was slow – I wanted to provide context about the things I thought about dating a widow or potentially deciding to date a widow. To catch up start here

Eek. So red flags 🚩 they aren’t fun facts about someone- they should be caution signs because you can really get hurt.

So after the park bench and talking, he kissed me on the cheek and parted ways. I had so much to think about…

I walked to my car – should have been walked to my car by him – so another red flag… about 2 minutes out of the garage, I get a call from Will apologizing about not walking me to my car.

It’s Dublin so I am not overtly concerned about safety. I am intrigued and get home to arrive to a text asking me to let him know I made it home safely which I texted.

I didn’t hear much for a few days and to be honest my head was full of thoughts and the lack of communication honestly was good for me because I didn’t play the dreaded “what if game”

I am anxious by nature and I dislike every bit of dating; from my stories you wouldn’t know it but I really just want my person and to be done with this charade. I figured this situation might be a good test to see how it goes.

So I get a call on Wednesday asking if I want to join for dinner and/ or ice cream. Well… I rarely turn down ice cream and Graeters is just one of the best places so I agree to meet. He shows up on a bike (I didn’t know he had one) without a helmet .. (not loving that) regardless happy to see him.

During ice cream time, we chat about life and I noticed something I hadn’t noticed before – his ring was still on. Another red flag đźš© I mean maybe I am insensitive but this is exactly what I was concerned about.

After 30 minutes of talking, it’s getting cold and I am in shorts and a tank and starting to chill – that’s my sign. He asks if we can go for a drive and talk – as long as I am driving okay in my suv.

I love to talk and drive with the windows down and heat on. I am not a huge fan of motorcycles and no helmet – but you do you boo. I won’t be joining – there are too many distracted drivers. The odds are not in your favor.

So, I am me – I don’t shy away from my thoughts or the elephants so band-aid rip off. I am looking for long term / marriage/ possible kids and he said he was content never dating again… until he saw some pictures of me and reached out .

So if you are serious about this, have given it thought, then why are you wearing the ring, why are you sugarcoating certain things? Even the keychain had a picture of the wife that passed.

I am new at this and am not trying to be insensitive but please pick a lane. I am living my life – living large and doing me – you reach out to me. You want to be with me. You also won’t let go of the past yet want both worlds…

I am not sure I can do this and it’s almost like I am convincing myself of something that won’t ever be.

So, I say I am not sure I can go on any dates because this is a lot. All of it. The ring, the keychain, the inability to dispose of things in the house, the inability to move forward honestly. To me, it’s like take it off if you are dating someone else or talk about when you might take it off… for me it is all kinds of awkward on the married hand.

A few days go by and I get a text asking to come over to talk. I entertain it; he comes over and pours he undying love out like vomit. Projectile love and it’s only been like 2-3 dates and no official kiss because I don’t know what lane he is even in.

I agree to go out again and question my sanity. We go to a concert and have a really good time. Despite the ring, the keychain and all the things I know it’s a really nice night – because I am not comfortable with the situation – I actually drove to the concert and met him. This is pretty telling because I prefer to go with someone to a concert and not to go alone….

I think all of the signs are flashing and it’s a sign that I deserve better – it’s not my job to fix a loss or to take on a project. I just have to be smart enough to walk away….. for now….(more episodes coming on what happens)

Would you feel similar?

Next Episode Did I just see your girlfriend on TikTok because it looks like your place?

Song for this Episode: End of the Line


A travel, home, & lifestyle blog written by Heidi Stevenson. Follow along for affordable ways to travel, sophisticated and savvy style, expensive looks for less for the home, and everyday style



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  1. 1.25.23
    Leslie said:

    Personally, none of those things would bother me. I see it as loyalty- he was loyal to her and would be loyal to you if you two got involved. But, my main rule is I don’t get engaged until 1 year of dating. After one year, I’ve seen enough to know what to expect. So, I would give him a chance.

    • 1.27.23
      trendywithapassport said:

      Stayed tuned. I give him a chance…