Dating in Columbus: A Series: Episode 13: Date with a Widow: Ghost Always Wins: Part 3

So to recap Part One Here and Part Two Here.

I won’t bore you with where I was at in the struggle and decision of where to go with this. As mentioned, the ice cream and concert really made me genuinely enjoy my time with Will.

On the way there we went to a restaurant I had not been to and was excited to try something new before the concert.

With my independence, I preferred to meet him at the restaurant and if he wanted to go to the concert together, I would be okay with that.

I get to the restaurant about 10 minutes before him and take a seat. When he comes in, he has a smile, a nervous look, and sensed something was different. I kept the conversation basic – how was your day; what is coming up at your workplace, and so on.

After dinner, I got up to grab my purse and he helped me out my jacket on, and opened the door on the way out; let’s be honest – in this decade, this is not common for guys. So, he opened the door to the car and I got in.

Half way to the concert, he reaches over and grabs my hand and lets me know that he wants to work through his insecurities, his baggage, and sees a future. After 20 years of friendship, he needs to move forward.

During the drive, addresses the ring and the keychain with how he felt that he didn’t end a marriage and that when he is ready he will remove it. He understands for someone else, it could be a thing.

I don’t want to argue about it. I have had people message like – he loved her and he was loyal and yes this is true. There is also living a lie.

To the outside world you are married, you are having a new relationship and not sharing this with other people and covert like Black Hawk Down or something.

While it is new and not something to address; there was also the almost divorce – they separated before her passing and then got back together – again, the layers of the onion are thick.

I am understanding and sensitive to a degree. He said if I decided to date him that there were things he felt obligated to do and I would need to be okay with the list.

1. Go to her family’s Christmas Eve, and her first husband’s family following that visit on Christmas Eve

2. Go on holiday vacations with the ex’s family

3. Spend the New Year with the ex’s family

4. For me to know that the other family would be prioritized

5. He likes to hang out with the ex’s sister and took a vacation with her in the summer and goes to events with her on occasion

6. Birthday celebrations – he will be at all of their birthday party shenanigans

Okay… as I said, I am understanding and empathetic but I am not a doormat. I understand relationships and spending time with family at the holidays especially under these circumstances.

I do not believe that it is normal or rational.

Let me address each of these with my thoughts.

1. Go to her family’s Christmas Eve, and her first husband’s family following that visit on Christmas Eve. My thought was okay to see them but does it have to be 5 pm- 11 pm? Do you have to do these things when you are moving on? Why would you find it essential to be at the ex wife’s first husbands family’s house – I’m uncomfortable and I’m not him. This is a red flag 🚩

2. Go on holiday vacations with the ex’s family I can understand going to their house or coming over – I do not think it’s appropriate to be vacationing often with them if you see dating someone else. Just unsettling red flag 🚩

3. Spend the New Year with the ex’s family In my world, New Year’s is a couples holiday and not time with the ex’s family. So basically, let me get this right…I can take care of you when you get old, spend every day with you but for instagram holidays – they have rank over me. I could say that this is new and I should let it go but if I am not a priority today, never will be. 🚩

4. For me to know that the other family would be prioritized Legit said this. I have been part of their family for a decade or so and I feel guilty and need to be there for them. It is sad what happened and just need you to know that their needs will be above yours. For me, another 🚩

5. He likes to hang out with the ex’s sister and took a vacation with her in the summer and goes to events with her on occasion Okay this one might take the cake. The sister set them up and has always had a crush on this guy. He even said – yeah she has always had a thing for me; yet you encourage it with the trip, dinners, and events together .. I think you, me and Dupree along with a ghost in this scenario – 🚩

6. Any birthday he will be there. I get going to things when invited; and if there is something going on, then send a gift and carry on. He informed me that travel, my own family birthdays- her family would take priority 🚩

Okay, so I repeated these items to make sure I really understood them and he said I got it, the last thing.. as if those were not a lot.. was that for church, he sits next to the sister in law with her family and if I was in the picture, I would need to accept that. 🚩

I asked about being included in the invites if the ex’s family and was specifically told – he didn’t want them to know he was dating 🚩

So one may say these are normal asks – I am a person who likes open and discussions – not these – feel like they are the rules or expectations and the layers of disrespect of me was more than I could handle.

I am not comfortable with being included when convenient and not allowed to be known or acknowledged – well for me, this was enough to call it a day.

I am not going to be a secret or an entity not known to others – the game and the scam was a lot from Will. He was acting like a grieving in spouse yet playing someone else to see how they can fit into the world he wants – to each their own but I was not signing up to be #2 to a ghost and her family.

I don’t apologize for feeling the way I do. I am not everyone’s tea but the keychain with her picture, the ring on, and the never ending list of requirements was enough to recognize that my worth is more than this and Peace Out Homie!

If you feel like you are in competition with a ghost – you are and remember

Ghost Always Wins

So you may want to know how I handled it; after the concert, he came over a few days later and I shared my level of unease with everything and Will immediately went to “I never should have tried to date, I like being alone” – let’s be honest here… he wanted me to allow him to do whatever he wanted and be okay with it.

I get to write the story in my life and no matter what – this would not have a happy ending for me. Sad but really true. I wish Will the best in his journey; it won’t be with me. We have been friends since high school and unfortunately this did not go as planned – thankfully after sharing how I felt; he respected what I said and agreed that it was for the best.

Would you have been okay with those items?

Next Episode: Gated Community Dating

Song: Ghost of You


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. 1.29.23
    Leslie said:

    No, all of that is beyond weird and that would have been a deal breaker for me as well. I’m sorry you were put in that situation!

    • 1.31.23
      trendywithapassport said:

      Thanks! It was hard – some of it I debated on things but it was frustrating as this was really not going to work out with no conversation or compromise