Skip Nav
32 Gifts Your Boyfriend Actually Wants
Self Improvement
The Worst Thing You Can Do After a Breakup — and What to Try Instead
The 16 Stages of Dating After Divorce

You Asked: Love Lost and Found

Dear Sugar,

An old friend has come back into my life. We were a serious item in high school and part of college, but instead of being a gentleman and breaking up with me maturely and civilly, he turned into a self-centered jerk and broke my heart.

A decade later, we're talking again. We both have grown up a lot, settled into our careers, and had our fair share of broken hearts, and we are both still single. We have started a friends with benefits relationship, but the problem is I feel like I'm falling in love with him. When I meet other people, I constantly compare them to him. Our friends tell me that he may be wanting more; however, I'm not sure if I want to be with him on that level purely out of self-protection. I know everyone deserves second chances, but I just don't know what I should do. — Blast From the Past Blair

To see DearSugar's answer

Dear Blast From the Past Blair,

Your relationship with this man sounds very complicated, so the best advice I can offer you is to talk openly and honestly with him about your feelings. We all know that friends with benefits can lead to a lot of confusion and often times a lot of heartache, so make sure you're on the same page before history repeats itself.

Just because you're in each others' lives again, you don't have to make any decisions on your relationship status just yet. Being cautious with your heart is a totally normal reaction, but if you think you're falling in love with him, you owe it to yourself to explore this relationship — like you said, we all deserve second chances. If at the end of the day it doesn't work out, at least you'll know you tried. Good luck to you.


Why It's Important to Be Responsive When Dating
Best Marriage Advice
Best Gifts For Men in Their 20s
Best Gifts For Men in Their 30s
From Our Partners
Latest Love
All the Latest From Ryan Reynolds