When people imagine doing things like flirting, approaching, or asking someone out, they think of these things as huge tasks. Therefore, they get overwhelmed, and then don’t end up doing anything; the key is to take it one step at a time. If you break it down, bit by bit, it all becomes manageable. 

The key to managing all of the above scenarios is to Test and Assess. In the example of approaching, first you test the situation by giving them some eye contact or a smile. Then you assess their response. Do they smile back, do they return the eye contact or, do they look away quickly, or even leave the area? It’s in this space of seeing how they react to you, that you know whether you should proceed to the next level. 

Today I am going to focus on how to ask someone out. Asking someone out is such a nice thing to do and it could lead to something really special. People do not do it because they are afraid of rejection. But, you don’t have to do a full on: ‘Excuse me, would you care to join me for dinner next Saturday? I could pick you up at 8pm.’ Don’t get me wrong, there are advantages to being so clear in your intention. Many people like it! If you regard rejection as an effective weeding out mechanism, separating those who you are a good match with from those who don’t, this clear way has many benefits. However, let’s say the situation is less clear cut. For instance, it’s someone at work. You don’t want to make things awkward if they do not reciprocate your interest. In this case, you Test and Assess

Test:‘Hey Jon, I was just going out to get a coffee. Do you need some fresh air? Care to join?’

Test:(after work situation) ‘Ah, I’ve had the longest day. I definitely need a drink. What about you, Deb? Are you heading home now or do you have time for a quick one?’

Test:‘I am going to go grab something for lunch. Do you want me to bring you back anything? Or, perhaps you don’t trust me and would like to come with me to make sure I get your order right!’

The next part, the assess, comes when you observe their reaction. Do they join you? Do they make up an obvious excuse why they can’t? Do they decline, but seem like they would have wanted to join you? If so, you just ask them again at a later date and see how they respond. Doing little tests like this and picking up cues in the assess period is how you can gauge if someone is interested, without you feeling like you are putting it all out there.