friendship ‘I Don’t Want To Lose My Friendship’ “I feel so conflicted. This is a friendship of over 20 years.” Kayla Kumari Upadhyaya — Feb 24, 2026
breakups ‘Well I’m Having Sex With an Ex. How Do I Make Sure I Don’t Catch Feelings?’ Congrats on finding a Sex With an Ex situation that actually sounds pretty low-drama! Now, how can we keep it that way? Kayla Kumari Upadhyaya — Feb 18, 2026
sex ‘How Can We Navigate My Girlfriend’s Sensitive Nipples?’ Sensory issues are also boundary issues. Summer Tao — Feb 3, 2026
life ‘I’m Obsessed With the Past. How Do I Move On?’ I think you have to go no contact with the past. Kayla Kumari Upadhyaya — Jan 27, 2026
sex ‘My Partner Wants To Sleep With a Cis Man Without Me’ Polyamory is a state of being, not an aspiration. You aren’t a worse person if you’re unwilling to engage in it. Summer Tao — Jan 20, 2026
life ‘I Desperately Want To Be Person Who Journals™ But Keep Failing. Help!’ “What are your fool-proof strategies for consistent journal use? Help me, the fool.” Kayla Kumari Upadhyaya — Jan 6, 2026
life ‘My New Year’s Resolution Is To Handle Rejections Better But Where Do I Start?’ A reader seeks advice after a year of romantic and literary rejection. Kayla Kumari Upadhyaya — Dec 30, 2025
breakups ‘How Do I Handle Losing Our Connection Post-Breakup?’ “It’s a strange grief. I know I’m the one who ended things, but we both still loved each other at the time and the circumstances didn’t line up.” Summer Tao — Dec 23, 2025
relationships ‘How Do I Cope With Uncertainty and Lack of Control in My Dating Life?’ “At 28 years old, none of my relationships have ever lasted to a year.” Kayla Kumari Upadhyaya — Dec 16, 2025
relationships ‘I Can’t Stop Obsessing Over My Girlfriend’s Ex-Girlfriend’ “Recently, I’ve found myself looking her ex’s profile or looking at old pictures of them on my girlfriend’s Instagram multiple times a day. I zoom in on the pictures &… Kayla Kumari Upadhyaya — Dec 9, 2025
friendship ‘My Friend Keeps Casually Saying Things I Associate With Disordered Eating’ “She’ll say things like how she ‘earned’ the mocha latte she’s drinking because of the long walk we just did.” Kayla Kumari Upadhyaya — Dec 2, 2025
dating ‘I’ve Dated Men for Three Decades. Is it Too Late To Start Dating Women?’ “I am a 50 year old woman who has exclusively dated men for the last 30 years. I dated a girl in highschool but it was a different (and very… Kayla Kumari Upadhyaya — Nov 25, 2025
