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You Asked: Is It Too Soon to Ask Her Out?

Dear Sugar,

I currently work with a woman who recently broke up with her boyfriend. Last year she thought he might be cheating on her and when she confronted him about it, he denied everything. She trusted him and let things go on, however last month, she found out the truth and broke up with him — she is completely heartbroken.

The few months leading up to their split, she would talk to me everyday about her situation; she'd ask for my advice, she'd ask for my support, and it seemed like she genuinely enjoyed my company. Nothing ever happened between us, but now that she is single again, I was wondering if you think it would be a good idea for me to ask her out? — Proceeding With Caution Chris

To see DearSugar's answer

Dear Proceeding With Caution Chris,

You say your co-worker is heartbroken, so while she's technically fair game, I'd give her a little time to mourn her failed relationship. In the meantime, continue to be her friend, but make sure you don't take on the role of her new best girlfriend — make subtle hints here and there to let her know you're interested in something more, but I advise you not to ask her out just yet in case she's not ready to be back in the dating scene again. Keep feeling out the situation, and when the time is right, I say go for it — ask her out — you have nothing to lose! Good luck.


Join The Conversation
lemassabielle lemassabielle 8 years
It's too soon to ask her but don't listen to that stuff about letting her find a rebound guy. I ended up dating my rebound guy for three years and fell madly in love with him. We did breakup but it was for legit reasons. Wait a few weeks and when she starts to pick up the pieces tell her that you're interested. In the meantime be nice to her.
JaimeLeah526 JaimeLeah526 8 years
I would be her friend but progressively get more flirty and when she seems to be getting better I'd tell her how I felt. I'd probably tell her that I liked her all along but didn't want to rush her.
babysoftpink babysoftpink 8 years
I meant to say "I admire your extreme FLEXIBILITY and is in fact very useful and good skill and mind set to have." Loyalty is the time of the past, indeed. :)
babysoftpink babysoftpink 8 years
I am extremely old fashioned, it takes 2 years usually for me to heal a six month relationship and be ready for the next relationship. If I was in a six year relationship, it probably takes 12 years to heal... :) The death of a relationship is as a death of a love one that takes time to heal, treasure, reflect and finally find peace in that all. so I am always very amazed at how soon and quick the other girls can get back into the game. I admire your extremely and is in fact very useful and good skill and mind set to have.
Marci Marci 8 years
I don't know. I was in a longterm relationship and met my fiance two weeks after we broke up. A part of me was thinking I 'needed time', but I also felt a pull towards him and just decided I'd be crazy not to check it out. So I'm not so sure about 'too soon' - based on my own experience.
sarah100682 sarah100682 8 years
I agree with everyone else. You need to wait. If you started something with her now, you would end up being the rebound. She needs time to mourn and deal with her situation.
jazzytummy jazzytummy 8 years
Everyone is right...give it time. She is in the mourning phase and trusts you to be her friend. She may see any other come on as a break in the trust and think you are trying to take advantage of her vulnerability. Don't you want to ask her when you know she is ready move on? If she still says no, then it just wasn't meant to be.
Swissabby Swissabby 8 years
I was in a similar situation, but the reverse. I was the girl in the bad relationship who confided in a close guy friend. I found out the guy I was dating was not a great person, we broke up. I didn't want to be with anyone for a while, and 5 months later, I realized I had strong feelings for my guy friend. I haven't acted on them, but they are there so there is hope, even if she used to confide in you about relationship problems. It just takes time!
Miss-Senorita Miss-Senorita 8 years
If you really like her then wait you don't wanna be a rebound.
kristyy kristyy 8 years
You guys work together - something else to keep in mind. What if she has no interest in you? Would working together after she rejects you be awkward?
gooniette gooniette 8 years
Hmm, if she was coming to you for a shoulder to cry on while her bad boyfriend was cheating, she probably isn't into you That way. And she will probably never be. Sorry dude. I'd not make a move at all, ever, unless you get some clear signals from her that she's interested. Otherwise, it will make the working relationship tense as well as your friendship.
designerel designerel 8 years
I agree with everyone here. She's probably going to be very distrustful of ALL men right now. Give her time. Don't swoop in on her like a hawk.
Jude-C Jude-C 8 years
Yeah, it's too soon.
pioneers pioneers 8 years
I agree with everything said, but must also add that she might just resent you if you ask her out this soon. I was in a really similar situation once, and I really relied on my friends for support. My best guy friend at the time was the only one who kept me from thinking that every guy is a total pig. Then, 3 weeks after the breakup, he admitted he had these feelings for me and tried to make a move. I actually felt pretty betrayed and we haven't been close since. Despite how nice he was, he just seemed like an unfortunate carbon copy of my ex, with one thing on his mind.
Myst Myst 8 years
I'm in agreement, it's way to soon, she's pretty vulnerable right now so it's not a good time to try to start something so soon. You've been waiting this long, so you can wait longer.
Simone-Grant Simone-Grant 8 years
reallysparkle nailed it - the first guy she gets involved with is going to be her rebound guy. And those relationships are rarely lastly, stable ones. If you're smart and you really like this woman I'd bide my time for a few months at least. Wait until she's started dating again and then ask her out.
Ac2366 Ac2366 8 years
Definitely too soon. I agree with sparkle, let her come to you. Just take things slow if you really like her. She needs a friend now, not a boyfriend. Everything is still too fresh.
reallysparkle reallysparkle 8 years
Way too soon unless you want to be the rebound. She is hurt and probably doesn't have much confidence in men right now. I'd give her space and not come onto her at all. If she wants to talk to you, she will.
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