#DILEMMAS · 5 ASKS

Should I go back to school at 34 to restart in a career I might not even land?

34, work in insurance, been there eleven years. good at it, paid well, completely dead inside about it. i've wanted to do nursing since i was a kid… Read more

#shouldi#work#school#dilemmas

66 votes · 3 comments · 2 options

Should I give my ex another shot a year after we ended it?

me, 27F. we dated three years and broke up last summer, not over anything ugly, no cheating. we just wanted different timelines, i wanted to settle… Read more

#shouldi#relationships#dilemmas

62 votes · 3 comments · 2 options

Should I burn my savings to go full-time on the thing I actually love?

34, married, no kids yet. i've been building furniture in my garage for six years, nights and weekends. this past year the orders got real, enough… Read more

#shouldi#work#money#dilemmas

109 votes · 3 comments · 2 options

Should I quit my job and move to Spain with $18k and no real plan?

i'm 31, single, work a fine marketing job that pays well and bores me into the ground. spent three weeks in valencia last spring and actually cried… Read more

#shouldi#travel#money#dilemmas

127 votes · 7 comments · 2 options

Should I break up with him before he proposes?

I'm 28, he's 30, together almost seven years since college. he was my first everything, first apartment, first serious relationship. when my dad was… Read more

#shouldi#relationships#dilemmas

91 votes · 4 comments · 2 options