Dating Two Men At The Same Time Is Totally Wild

"I can honestly say I've never dated two men at once until now. Have I dated? Yes, of course. But going out on dates with men, having a few dates with one guy and a few dates with another at the same time to test the waters is different than intentionally, exclusively dating two men at the same time because that's all I have energy for."

"I'm not being sneaky by any means; they both know that I'm dating because I've been clear that's what I'll be doing until I want to commit to one man. For me, that takes a while. In the past, I've committed too fast, ruled out all other possibilities, and been very, very sorry. At this stage in life, with divorces and kids and baggage (because we all have it), it takes longer to get to know someone."

"When they both text me a sweet good morning message, there have been times I've almost gotten back to the wrong man. It wouldn't be the end of the world, but I'm sure it would feel shitty to them because I know it would feel shitty to me. There have been a few evenings when one man has called while I'm on a date with the other, and it's been a few hours until I was able to call them back."

"Now, thankfully, they are both respectful of my time, and when they ask what I was up to and I tell them I was at dinner, they don't ask me any more questions. It's like a silent understanding, but it still feels strange to me. Dishonest even. And yet I keep doing it because I owe it to myself to take my time. And the reality is that we are dating, and I'm not doing anything wrong."

A woman is intentionally dating two men at the same time, with both men aware, to avoid committing too quickly after past mistakes. She values taking time to assess compatibility because later-life relationships often involve divorces, children, and accumulated baggage. Practical challenges arise, such as nearly replying to the wrong person, missed calls while on other dates, and an uneasy, silent understanding about each other's schedules. The arrangement feels at times dishonest despite transparency. She avoids sexual intimacy because of monogamous values, feels sexual desire for both men, and believes a period of testing is necessary.

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