Her Sister's Keeper

Dear Bro Jo,

This problem is about my sister, who is 24. She is stuck in a "hanging out situation". She really likes this guy who is actually 33. They hang out in large group settings, and she would really like him to ask her out. I don't know much about the whole situation (I tried getting her to send you an email, but she refuses), but he sounds like he's somewhat interested in her. He's been touchy (again, I don't know how far--if like he's held her hand) and he texts her often. Recently they saw a show with a group of friends. After the intermission, he asked her to sit by him, just the pair of them away from the rest of the group.

I've tried telling her that she should tell this boy that she'd like to get to know him on a more personal, one-on-one level, but she's afraid of rejection (just like everyone).
And I don't know why he's not married at 33--maybe because he lacks the skills to ask girls out, like when it comes to my sister. She really really likes him, and it seems like she's settling for friendship because he has yet to ask her out. This "hanging out" has occurred for over a month now--almost two, I think.

What should my sister do? Should she just move on? Stop having him text her? Or should she continue to wait for him to ask her out?

--A Concerned Sister


Dear Sister,

If she's 24 and he's 33 she needs to apply a little pressure (maybe A LOT of pressure . . .); using one of the "Bro Jo's HOW a GIRL CAN GET a GUY to ASK HER OUT" techniques may help (email her the Facebook Note link). "Hanging out" rarely gets a girl where she ought to be, and waiting is how we end up alone and never married at 40 . . .

That said, you (and I) need to realize that your sister isn't asking for help. She's got to make her own choices and her own decisions. Perhaps she's inspired to have some reservations about liking this guy; maybe she's just not ready.

Sure, I think she should date - if not this guy then certainly someone else, but we can't force people to get married, Sister. Unless she asks for our advice or help, she's on her own.

- Bro Jo