Am I Allowed To Ask Again?

Tuesday | December 2, 2014

Love Letters Relationships

Am I Allowed To Ask Again?

I am a little confused about something. Over a year ago I asked out a woman I work with. She turned me down saying she is not interested in dating anyone right now. So at first I assumed she was just letting me down easy and was not interested. Since then she has become flirty and often initiates conversations, asking about my life and revealing things about her life to me.

I do really like this woman and I am pretty sure she is still single. I do want to ask her out again but I am a little hesitant and do not want to seem desperate. Do you think I should just let this go? I think about her all the time and she is a really great person. So should I take the chance and ask her again?

– Confused, Andover

If this woman is capable of flirting with you and asking about your life, she is also capable of asking you out and telling you that she changed her mind about dating. You can be kind and receptive so she knows you’re open to her attention, but there’s no need for you to ask her out again. It’s best to leave the ball in her court, especially because you work together.

But please don’t wait around for her to decide that she wants more. It’s possible that she just wants a friendship. It’s possible that she just likes office banter. Keep looking for other women, because thinking about your coworker all of the time isn’t going to help anyone.

Readers? Is he allowed to ask again?

– Meredith

Relationships