Should I Ask Him Out? [LISTENER E-MAIL]

Lori writes:

I heard you talking on the radio a few weeks back about a girl that had a relationship question so I thought I would give it a shot, maybe your audience can help.

Every morning on my way into work, I stop at Zootown Brew and have my coffee and a muffin. For the past two months, I have been joined by a guy who also frequents the coffee shop before work.

We have started sharing a table and great conversation every morning. He has told me he is single and it’s obvious we are both flirting and enjoying each other, but he never asks me out! He hasn’t even asked me for my number.

I would really love to see if our breakfast friendship could turn into something more, but he won’t take the first step. So, should I ask him out, or should I keep playing it cool and hope that he mans up sooner rather than later? Or, do you think he is hiding something?

Thanks,
Lori

Lori,

Thanks for listening and taking the time to email us! I’m no relationship expert, but if you ask me I think your coffee shop guy may be one of the few nice guys left in the world. In this age of cell phones and instant EVERYTHING, I think it’s pretty cool that things are moving at a snail’s pace with your new friend. It seems obvious you both like each other, so why not play it cool and see where it ends up? My step dad always said, “good things come to those who wait,” and I truly believe that. The real question is: how long are you willing to wait for him to break the ice? Do you think it’s bad form for you to ask him out or are you afraid of the possibility of rejection? If you’re enjoying coffee and conversation anyway, I say play it cool and enjoy your time together. Then again, there’s always the chance he’s gay and will become the Will to your Grace – which isn’t the worst outcome. Good luck, I hope it works out for the best!

What do you think of Lori’s situation? What advise do you have?