Do I or Don't I??

iVillage Member
Registered: 03-30-2011
Do I or Don't I??
Wed, 03-30-2011 - 7:32pm
Ok, here is the deal....I ran into a guy I went to high school with!! We have bumped into each other maybe 3 time at the grocery store of all places!!) in the past month or so...There is an attraction, I can feel it. His daughter has been with him everytime or I would really flirt!! My question is: Is is okay for me to look him up and call and ask him out myself? I know he is divorced...he is not on facebook, and I have not "run" into him again in the past few weeks! Should I just call him and ask him out on a date? Or is that a bit forward? I am recently divorced (8 months )...a little rusty when it comes to dating! Thank you!
iVillage Member
Registered: 11-28-1999
Wed, 03-30-2011 - 9:55pm

Since you already know this guy I dont' see any problem w/ calling him--but instead of phrasing it like it's a date, try to make it seem like "Hey, since we've met in the store and you've been busy w/ your DD, would there be some time you would like to get together & catch up on old times?"

iVillage Member
Registered: 12-05-2010
Thu, 03-31-2011 - 12:27am


Hi. Go for it. Ask him out. The worst that can happen is he'll say no. If he is interested, he'll be happy you took the first step.

iVillage Member
Registered: 12-27-2008
Thu, 03-31-2011 - 8:12am
I am bold but not that bold. I tend to prefer softer rejections than a flat out "No, I don't want to date you" (which, I don't care how confident I can be, that stings). The reason you risk the straight rejection is because he hasn't asked you out and often-times a guy will make the first move if he's interested. The fact that he's divorced does not mean he's single and the fact that he's single won't mean that he's interested you. But that you haven't been able to flirt may mean that he doesn't know you are interested and hence the lack of follow up on his part.

But, and in sum, I would play footsie first before making a bold move so as to allow room for a soft landing.

So, it is often in our nature to misconstrue innocent pings as interest. Relying on this principle, if it were me, I would ping him and simply say: "Hey, haven't seen you at the grocery story lately. Your daughter is adorable. How are things with you?" And see how he responds. If he responds: "Thanks for checkingin. I've been hanging out with my girl friend a lot," well, there's one answer. He could say "Thanks! It was nice to see you. How are you?" At which point you could ask him to coffee. Or he could say "Gosh, it's great to hear from you! Are you seeing anyone? Want to have dinner?"

So I think a simply text is a good first step, and it allows for that softer landing.