The Situationship, give me your opinions please

Okay this is going to be a long one: 8ish months ago, this guy I gave my number to text me after a week. He was a delivery driver for my job, we saw each other once or twice a week, for about 2 years, just causal convo in passing until I gave him my number. Quickly that turned into texting sometimes then to snapping atleast 8 solid hours out of the day, nudies normal pics just daily convos, as well as me walking out to his truck and sneaking some kisses and touch’s. A month in we decided to meet up for the first time outside of work, I though we was hooking up, but not turned into a breakfast, quick walk holding hands through the store and some kisses before we left each other and continued what we had been doing with the talking all day blah blah for another 2 weeks.

Here’s some back info: he’s engaged, I’m married and neither of our partners were ok with us seeing or talking to other people, we both have 1 kid seperate from our current partners. We live 1.5 hours from each other, and have a 10 year age gap (44-34) me being younger.

We end up picking to meet up at a hotel, early in the morning and spent the day together, with the intentions of having some drinks, hooking up and leaving each other. But that turned into sex, going it to eat and walking in the snow together. His fiancée called him, he responded with a lie, she called again crying, and I ended up dressing him and we left. He said he didn’t want to go home but to stay with me, but I couldn’t, had to go home to my family.

We continued to talk after this, he was more insecure about as often when he was at home, but was still atleast 6-10 times an hour minimum. Still same stuff at work and lots of snapping during work hours. We met up a couple more times at hotels that month no partners calling, was just good fun sex, snuggles and food.

Our conversations went from casual, to talking to each other about our personal lives, advice with kids, friends work and making decisions together. With some I think I might love you in there, me getting pics of his fiancée making breakfasts and going shopping, and soo forth.

We are both, obviously, sexually engaged kind of people (willing to swing, 3 sum whatever) and 2 months in created this plan, he told his fiancée they were taking a mini romantic weekend to a different town, and I was to meet them at the bar and try to get her to let me go back to the hotel with them. Soo we meet at the bar, they pregamed a little, she had a good buzz, he got up to go to the bathroom and i went over and shot my shot with her. I could tell she was a touch intimidated soo I just asked her if she wanted a drink, and she accepted. He got out the bathroom and she bolted out of the bar, he was able to talk her back in, I gave her a drink, she slammed it, and she left again. Long story for this part short, they end up fighting. And he leaves her at the hotel and meets up with me, he have more drinks, and got a separate room from her in the same hotel and hooked up and stayed the night together. 5am comes, knock on the door, it’s the cops, she reported him missing (his name was on the room) said they wouldn’t tell her where he was, but that he was safe. We ended up leaving each other about 3 hours after.
He go back to her, they fight fuck and make up, and he tell her the truth about everything.
At this point. He texts me and says me and him are done and he doesn’t want to throw his relationship away, blah blah.

I was pretty hurt, but also emotionally overwhelmed and it was starting to affect my family as I wasn’t as focused as normal-spending time away, and on my phone all the time. We went about 3 days no talking and he messaged me, asks how I am, says he misses me. And it all starts up again, But it’s different than before it was still the i miss you need you crave you want to see you, still stuff at work, but was starting to come with wanting it one day and not the next. Another weekish goes by, he takes her on a vacation for her birthday. He’s NOT supposed to be talking to me but definitely still was. They were at the bar, he walked away from her on her birthday and he calls me, she catches him. She leaves him there, and flies back home, starting the end of their relationship. I talk to him the entire rest of the time he’s there, and when he got back, I saw him 2 days later at work.

We are like 2.5 months in to this situationship.
I like him, a lot. He says he likes me a lot.
I ended up getting into a bad fight with my husband, and forced him to leave. It was hard, but we had some toxicity due to drinking already in our relationship.

Us both being separated allowed us to spend a lot more time with each other. While we emotionally bonded about our partners being gone, supporting each other through that as well as the sex, drinking, food blah like normal. I went to his house, he went to mine.
We went on little weekend vacations together, one where I met some of his friends-who ultimately didn’t like me based on what happened-too over the next few months, spending like 5 days a week with each other, flying out to different little vacations and concerts. During these times, After like 3 days of being with each other, almost always we would fight, we both struggled with our alcohol limitations and would emotionally bomb each other, all truths coming out.

We had no boundaries, no clarity. We tried. Some days he wants to fix it with her, he would say it’s our last time meeting, and go 2-3 days and come right back and we are starting again..
During our off times, I was picking up my husband and we were talking and trying to work on things, but always when he messaged me, I would let it all go and just repeat repeat.

The last time I saw him, about 3 weeks ago, we had done a little vacation, and were back at his house. He lays in bed, and tells me he misses her. I was just exhausted at this point mentally, and I got on Facebook messenger and sent her a message, she asks me to call her almost immediately, we talked, cried with each other, thanks one another. And I told her he needs her and I was going to let him be, if he so wishes.
All of this was right in front on him, naturally I didn’t leave right away I had to pack up all my things, sex around a bit. Then we kissed each other good bye, and went without talking for a few days before he said hey and here we go again… I was out with my girlfriends at the time and called him, and made a bit of a fool of myself (I don’t remember tbh) and it angered him, to the point where he told me dont talk to him and sober up…next morning i get up to an email from him, saying he’s done. He’s going to work on things with her, it’s over.

I ended up having an emotional breakdown, had to have some people listen to me vent, and did a little self help to regain my confidence.
A weeknish goes by, nothing.
Then 5 days ago, he messages me “hope you are going okay”.
I didn’t respond immediately, I didn’t know if I even wanted too. Soo I went to bed and when I got up I responded. It started slow the first day, then immediately back to snapping, all day talks, calls on the phone then immediate texting, and we have plans to go to a concert together this weekend, where I stay with him fri at his house and Saturday at hotel.

While we been talking these last 5 days. He says he made himself a dating account, and showed me pictures of one of the matches that responded to him, says they have been chatting, and that she’s interested in meeting up with the both of us to hook up, which is whatever that’s fun…
but I had to set a boundary for the first time and told him, we can hook up with other people together, but not without one another, he agreed. I told him I can’t do a relationship, he asks why not, i said we would have to take time and really figure out if that’s what we could be, he agrees but we didn’t choose to initiate that…He’s telling me he’s missing me, doesn’t know how he got soo addicted to me. Last night while talking he says he loves me and can’t wait to see me. I said you know it’s mutual. Today all the same shit messages all day snaps and phone calls, I tell him I’m not going to be around forever, don’t want to be a rebound and that if we can’t do the boundary, I’m completely done. He doesnt wasn’t to be done soo it was a good night love you talk to you in the morning. Here I am writing this now…

I’m soo completely lost with it all there’s apart of me that’s like, good lord girl just stop, and there’s the other part of me where I do really like him and how he makes me feel. I know we are both extremely attracted to one another. I probably would be willing to be exclusive to just him, but I’m not going to put my guard down for it.
8ish months, nothing compared to my 10 year marriage and his 11 year engagement.
But wow it’s wild all the feelings situationships bring and what happens

Anyway hope you all enjoyed, I’m not an English major soo let my shitty structure and grammar go please. Otherwise bring on the questions and comments.

Posted Jun 11, 2026, 2:29 AM UTC

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