I think we have all had bad experiences with rejection before. There is definitely a right way and a wrong way to go about starting a conversation with someone you are interested in. I’m sharing these tips from what has worked on me and the ones that have been successful with other people. In general, as long as you’re being sincere, casual, and not sleazy, you will have much more success. Never try to come off as though your whole point in talking to them is to start flirting with them.
Most of the time, it’s best not to start out with a line about how beautiful they are, especially if it’s about their body. This tends to tip them off that you are shallow and only interested in hooking up. Just start the conversation casually by talking about something that you can tell they are interested in. If they are reading or carrying a book that you’ve read or know about, start talking to them about that. If you meet them in a bar, you can start talking with them about one of the other people in the bar who might be particularly obnoxious, or what’s playing on the bar’s TV. You can also start talking about something interesting that you’ve done recently. Here are some of the best pick-up lines:
“Oh no! How did they screw up that play!? Man it’s hard being a Mets fan sometimes.” Just start talking to them without any indication that you’re interested in them. This will take them off their guard and let you slip in undetected. This way, flirting with them won’t seem fake and shallow.
“Hey, how’s it going? You look kind of tired, been having a tough day? I just got off work myself, definitely ready to relax.” If you have a good job, you might mention what that is. Success is quite attractive to most people, but so is being hard working and dedicated.
“You know you look like you’ve got some French in you. Are you part European?” This is one of the few ways to give someone a subtle compliment about their looks without setting off their pick-up line radar. Telling someone they look European is usually considered to be a compliment, as it is often associated with being trendy and cool, but it’s not openly a come-on.