Determined to ask a friend out, but now having serious doubts

She (27F) and I (27M) have worked closely together for a couple of years. The first year our relationship was strictly professional, but we’ve become pretty good friends over the last year. During that time, I started developing feelings for her, but I buried them because she was in a relationship. Plus, I was happy with our friendship and I don’t think you can be a good friend to someone while romantically interested in them.

But I always told myself that if she ever becomes single, I’d ask her out. Well, it turns out she broke up with her boyfriend before quarantine arrived. I’ve spent so much of my life running from romantic connections and avoiding being vulnerable with others, that I promised myself that this time I’d have courage. I’d stop having regrets and what-ifs, and finally find the courage and take a leap of faith. Whatever the outcome, I could be proud of myself for never giving up hope.

But the more I think and stew in quarantine, the more doubts creep in. What if this is a bad idea? Our desks at work are right next to each other and we work on the same team. No avoiding each other if things go sour. What if we actually aren’t that compatible? What if she doesn’t have any feelings for me, and now feels too awkward to interact with me anymore? Before, it was just a fantasy. Now, the prospect of potentially ruining a friendship, and embarrassing myself in the process, is terrifying.

I feel trapped between my head and my heart. It feels like personal growth for me to finally put myself out there and risk being hurt and rejected, but another part of me thinks it’s mature to be cognizant of the potential fallout from this decision. Absolutely no clue what to do here. Any advice would be appreciated.

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