How many times?

I don't think it hurts to ask again a couple times, particularly if you are just asking her to do lunch or grab a cup of coffee. Just don't make yourself a pest about it.

I don't think it hurts to ask again a couple times, particularly if you are just asking her to do lunch or grab a cup of coffee or something innocuous and friendly like that. She may have a boyfriend ... so don't make yourself a pest about it.

Since the last question I submitted here got 4 pages of responses and all seemingly agreeing with each other, I thought of another.

How many times should you ask someone out before finally moving on?
Is it one and done?
Or if the two of you get along, do you wait a while and try again?
How many is too many?


In my mind, I have the idea of one and done. You know, I ask her out and get a no. She knows I am interested so if she changes her mind, wouldn't she then come to me and ask? I just can't help but think that the response could be something like "didn't you hear me say no last time?" (more negative sounding than intended)

I think it varies. Never hurts to try again since some people might have had plans. A match I wrote about in another post hasn't bothered to try again, so I'm not sure what to think of him.

He asked me out for a Sunday night concert about four days beforehand, but at that point I already had plans. It also would require me buying a plane ticket or driving 5 hours to the city where he lives. I already had plans for a family birthday celebration that day, so it was not possible. And he did not offer to help pay for part of a plane ticket or hotel room either. Not that I couldn't pay for that myself, but it would have been a nice gesture since he was the one who asked me to travel down there.

I politely declined and told him of my other plans, but said I'd really love for us to meet up another weekend. He said he'd be coming up this way later in the month to visit one of his father's ranches and I said how I'd be back in his city the first wkend of Nov. Well, we talked on the phone for the first time 9 days ago, I sent him a quick text message the following day to say I had enjoyed talking with him and hoped he was having a good day at work. Haven't heard from him since. Also sent him a quick email this past Monday asking how his wkend went. Not a peep. I am thinking he just doesn't have the guts to tell me he's not that interested anymore. Oh well.

So.... "Don't be a pest, but be available for me if I want you."

These two are obviously young and in college and I think it's quite possible she's becoming interested in him from what he's posted. Sometimes a relationship takes time to develop, too, and the circumstances may change enough where asking again is OK.