Portland Dating Dispatch

I went on a second date that I knew I should not have gone on with a guy from Plenty of Fish. We arranged to meet at Pioneer Square and go for coffee. I overslept and texted that I would be a bit late. He was the one who looked like the Unibomber. I suggested […]

This. After 2 lovely dates. “Hey, I hope your trip was super fun. Just wanted to to say that I am dating someone (his ex) and it may be getting more serious, so that’s why I haven’t followed up with you. Will let you wow if that changes because I had a good time with […]

Online, she seemed nice enough through our messaging. The red-flag that I now know to look out for was unknown to me at the time: No clear photos posted. We met at the Spaceroom and when she arrived, I didn’t even know it was her; that’s how vague her photos were. Not to be rude, […]

Dear Sara,We matched on tinder and after a short conversation, I asked you out. 12 hours later, you told me you were just looking for friends, which is totally valid and fine with me. You didn’t know that I was super stoned at the time and hate texting when I’m high. I should have just […]

I met a guy on OKC and we dated for a while. At first he said he lived in Portland, but actually live north of Vancouver, WA. Small lie, but he was nice, albeit strange. Then he started to go crazy; talking about the barrel of a gun looking mighty tasty, questioning the loyalty of […]

We meet at the climbing gym and he greets me looking concerned and says, ” I just want to make it clear that I don’t have any money. I got a buddy pass for you to get in, and I packed food so don’t expect to go out anywhere.” Ok fine. I appreciate the creativity […]

There was this girl that I had been talking to on tinder for about 2 weeks that lived in central Oregon while I lived in Portland. One day she offered to come and get me (didn’t have a car at the time) and bring me down to visit for a night. I was on the […]

I met a cool lady at a comedy show this winter who knew a lot about music and liked to drink bourbon. She also had that cool gothy look that I like. She was friendly and smart and we got along great so we started dating exclusively. So Valentine’s day morning comes and she breaks […]

We went to her place. She cooked steak. There was a lot of wine. We ended up in bed but before the sex started, she began to cry. I asked what was wrong but she wouldn’t say. I think I tried to be nice but my frustration was probably pretty evident. I had my arms […]

I was hanging out by the Hollywood District and had gotten a message from some guy on Tinder that wanted to meet up, so being about 5 drinks deep I thought it was a great idea to meet up with a complete stranger a 9 pm. But I did end up dragging my friends along, […]

I have seen this guy off and on for 3.5 years. When we were initially dating it was amazing and I thought I had found my person. Not too long in he got freaked out, seems to be a thing for new divorcees. He ghosted. Then later came back. Over the years this became a […]

Met a guy on okcupid, and while not the type of guy I usually date he seemed fun. We hit it off and started seeing each other. About 2 weeks in, after we had slept together, he told me he lied about his age, he’s actually 11 years older than me not 6, and he […]