How Many Times Before Giving Up


Actually a really good question. Go figure.Every Tuesday, we ask people from Team Wingman & Twitter what they would like me to talk about. It could be a general topic or a direct question. I’ll choose the best one and later that day, I’ll write something and give tips addressing that topic or question.

This week’s question: How many times do you ask someone to hang out before giving up / waiting for them to reach out?


We’ve all been there. You meet someone very cool, you’re interested in them and you even get a number! Good job!

But then, something happens. You either call and don’t hear back or maybe you do call and even go as far as getting them to say yes to a date. But then they flake out or cancel plans.

It takes so many times before you have to decide to move on from this person. Here is the breakdown -- with a timeline -- of when and how you should be contacting the person.

1st contact: within 24-48 hours. This goes back to my rant about the “three-day rule.” If you two had a good conversation and want to see them again, say so, and say it sooner than later.

When you get on the phone with them, keep the conversation short (5-7 minutes), light and fun. When you can catch a good moment where you two are having a good laugh or feeling good, ask them to hang out.

If you’re not clear with your date idea, it’s more likely they will flake.

TIP: Have something you’re already going to do and invite her to it -- of course, knowing it’s something she’ll enjoy. If you don’t have anything going on, meeting up for drinks is good enough. Just be specific.

2nd contact: 3 days after first contact. If they flaked on you or didn’t respond, try to reconnect with them. DO NOT reconnect and then ask them out. Women can tell if a conversation is objective-based and it can be a major turn-off.

Instead, catch up with how things are going and gauge their interest in you and the conversation based on her replies and questions she asks you.

If the reciprocity in the conversation is there, then definitely make a move. If not, wait for the next conversation (in a day or two) before asking them out.

3rd contact: 7 days after 2nd contact. At this point, nearly two weeks have gone by and your dates were either continuously pushed back or you've heard no response. You still want to follow the same guidelines as the 2nd contact but because it’s been almost 2 weeks, the attraction and momentum is lost and they need to feel those things again.

After your attempts to rebuild the attraction and momentum, if they aren’t positive in their response, if any, then it’s time to move on.

If the person you’re interested in can’t put it together to spend time with you -- or at the very least, return calls / texts -- chances are they have too busy of a lifestyle that can work for you or they are just not interested.

At the end of the day, it’ll always be better to know, than not.