Co-Worker Interested in Dating Older Widow
Dear Abby | November 25th, 2025 | Letter 2 of 2
DEAR ABBY: My best friend and co-worker is 57. I'm 32. Her husband died two years ago, leaving her and her 22-year-old son alone. We've been best friends and co-workers for the last six years, but over the last few months, I've been realizing she's a lot more to me than just a friend. I am nervous about trying to make advances because I don't know if the feelings are mutual or how she views our age difference. I don't want to risk ruining our friendship. I just know that my heart skips a few beats when our eyes meet or our fingers accidently touch. I've realized these last few months that I'm falling hard for her, and I'm afraid to let her know. If I don't, however, my feelings are going to eat me alive. What should I do? -- FALLING FOR HER IN KANSAS.
DEAR FALLING: Ask your best friend (and co-worker) to join you for a casual lunch or dinner. Keep it light but tell her how much you enjoy her company and ask if the age difference between you bothers her. If the answer is no, explain that you care very much for her and wonder if she'd be open to the idea of dating you. If she says yes, and there are rules at your job that discourage fraternizing, you may have to find another place to work. If she responds that dating would be awkward, let her know you will always be her friend because you think she is special.
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