Portland Dating Dispatch

When I walked into your apartment, I could see your daughter eating her dinner at a little kid’s table. I was shocked that she was there, because I was a stranger to you. Hey, I know that I’m a nice guy… but YOU don’t know that. I knew you had a kid, but I thought […]

Sometimes you go on Tinder because you’ve been fed the, “i want to fuck other people too” line out of the blue from your monogamous current beau. So naturally, you decide to search for some too. Sometimes you go on one damn date on the app shortly after said line and meet the sweetest dude […]

The next time you feel bad about your life choices, consider that one time I took a girl on a date to an arcade… where she gently reminded me that she was epileptic.

I started taking antidepressants and about a month in I found myself feeling lonely, on a weekend, posting a Craigslist w4m ad, IN THE MIDWEST. One of my responses was actually a friend of a friend. He had seen my photo in her FB friends. I agreed to meet up that night to watch a […]

So in LOVE. I mean real LOVE! Like the kind you feel way deep down and you know everything is right in the universe, everything aligns perfectly. Time and space are totally on your side. You have found the one. You are the one. OMG love is real! But then they’re like, “I totally care […]

So I am walking, enjoying an early evening on Hawthorne. A cute guy is sitting on a bus bench, nods, gives the “what’s up?”, line. I stop and we chit chat. He’s pretty cute, and we start having an intense convo. Love, life, freedom- all in a span of 5 minutes. We are hitting it […]

I had lost the job I had for 19 years,and a perianial single man. One woman I wanted to marry ultimately didn’t want me: one I should have. Now over 50, dates treated me with an air of suspicion: red flagged for never marrying . Never mind the baggage many of the women I met […]

I’m done with dating men in this town. Seriously, all of the men I’ve gone out have been little boys. I gave them ALL fair warning that I would bring my child on our first date and yet upon meeting, they freak out. I don’t believe in sacrificing time with my son for time with […]

I had an extra ticket to Nixon In China at the Keller and experienced a dearth of acquaintances who were down for John Adams. Humorous ad on CL and waded through a few replies, but no actual takers. You said you’d never been to the opera, showed decent email grammar and that was enough for […]

Meet girl organically through work. She lives in another town. Same company. Me? Never had a viable connection with another human being. We connected. Make a date for when she’s in town. Go get burgers and beer downtown. Mid bite on my burger she mentions the other men she’s dating. I couldn’t finish my food. […]

I met a man on some gay chat app. He was handsome and seemed nice so we agreed to meet. We had several dates and one night he ended up staying over and we cuddled by the fire. The next morning I dropped him at home and he said he would call me later. Days […]