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Taking It To The Next Level — Delilah’s Dilemma


Going from being just a friend to asking to be in a relationship is a drastic step for many people.

A loyal listener of Delilah has this exact problem with a coworker of his:

Dear Delilah,

I have a friend who I’ve known for several years. We work together a couple days a week and recently we started walking together in the evenings. We have very interesting conversations when we walk and we solve all of the world’s problems together. We also get together on weekends and go shopping or just hang out. We have a lot of fun and make each other laugh. She has a 17-year-old daughter that will go places with us. This has been going on for about three months. I’ve developed strong romantic feelings for her over this time. I want to tell her how I feel but I don’t know how she feels and I don’t want to jeopardize our friendship. I’m afraid I’m going to get all tongue-tied. What should I say to her? David

Dear David,

You need to be bold and find out if there is a possibility of a romance between you two because you aren’t getting any younger! You can accomplish this in a variety of ways: you can buy her a card, send her an email, dedicate a song to her. You just have to end with a question and say, “You are my best friend in the world but I would like more than a friendship. How do you feel?” Give her permission to be honest with you and not feel pressured by you. She’s either going to respond with, “What took you so long to figure this out!?” Or she’s going to say, “We have a precious friendship but I’m not romantically into you.” Either way you need to know, otherwise, you could miss out on a wonderful relationship. So be bold and accept whatever her decision is. Good luck! Delilah

What would YOU do if you gained stronger feelings toward just a friend? Comment below!

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Rachel Specht contributed to this post

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