Ask Ursula: After being in the ‘friend-zone’ for years, should I finally ask my former co-worker out?

Hi, I’m Ursula Reutin, co-host of “The Gee and Ursula Show,” and welcome to my advice column, Ask Ursula, where I help people navigate family, friendships, work, and all the messy, beautiful moments in between.

If you need any advice, reach out to me at askursula@bonneville.com or fill out this form here.

Good guy looking for a chance

Dear Ursula,

I have been friends with a lady from work (neither of us work at this company anymore) for about five years. Over the last year and a half, I feel we have gotten closer. We text each other “good morning” every day. She calls me almost every evening (we usually talk for three to four hours) when she gets home from work.

I would like to take things to the next level in our relationship, but I feel like I have been “friend-zoned.” Occasionally, she will mention going out or making plans with other guys, only to share how she was disappointed by the experience. She seems to pick guys who are disrespectful and self-centered (bad boy syndrome). She also had a terrible marriage (with a bad boy, of course!).

I am the total opposite (good guy). I know we would have a great time if she gave me a chance. I know she has some kind of interest in me. We enjoy each other’s company whether in person or on the phone. Now that we seem closer, should I just take the plunge and ask her out on a real date? I can really see a future with her. The only thing that is holding me back is that when we first met, she turned me down.

That said, I also have to admit that if she rejected me and later started dating someone else, I would probably pull back from the friendship. I might continue occasional lunches, but I can’t keep having hours-long conversations every day.

Give the good guy a chance!

Dear Good Guy looking for a chance,

YES, I think you should take the plunge!

This friendship has already moved beyond something that feels casual or emotionally sustainable for you. You are spending hours talking every day, thinking about a future together, and hoping all of that closeness will eventually become romantic.

And you have already admitted that if she dates someone else, you will need to pull back. That tells me you don’t want to stay in this exact friendship indefinitely. You’re emotionally invested, and pretending otherwise will only make you more frustrated and confused.

So yes, you need to be honest with her.

But you also need to be careful NOT to make this a huge declaration of love. Don’t point out that you think she’s choosing the wrong men and should finally give the “good guy” a chance. She does not owe you romance because you’ve treated her well.   I’m sure you don’t want her saying yes because she feels guilty or is afraid of losing your friendship.

Keep it simple and direct: “I value our friendship, but my feelings have grown into something more. Would you be open to going on an actual date with me?”

Then let her answer.

Best-case scenario, she might also have feelings and has been waiting for you to make a move. There is also a very real possibility that she loves you as a friend, but is simply not attracted to you romantically.

You need to be ready for either answer!

If she says yes, wonderful. You finally get to find out whether this can become the relationship you imagine.

If she says no, believe her! Don’t argue that you would treat her better than the other men she has dated. Don’t continue the same intense friendship while secretly hoping she will eventually change her mind. That might never happen. It would be totally fair to tell her that you care about her but need some distance to reset your own feelings.

Bottom line: Ask her out clearly, respectfully, and once. Then accept the answer she gives you.

Good luck!

With love,

Ursula

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