Don't try to build up false hopes; bracing yourself throughout this process could be helpful as interfering with a relationship can really complicate things. Get their attention. I think it's best dating site time for a break. Before you write your profile, see what people your similar age and gender are saying about themselves. If you're not ready just tell him. Suggest a range of different things of interest to you, and also do things of interest to your date, and see how their level of enthusiasm (or lack of it) leaves you feeling. Step Outside of your boundaries - Take a visit to a club where you know that Bad Boys hang out at in your city, some place where the men won't be dressed in a suit on the dance floor. Are you and your neighbor single? However, don't be put off if you can't think of something clever or funny. Decide which one of the options would make you a better person. When you start to talk make sure you are not arguing. Don't play around with a single mom. You'll find it too. There are many one-liners you can find with a search on the internet, but here's a sample of one-liners showing how you might use them. Then there are spots that are notoriously saturated with testosterone: the gym, an Apple store, a political rally, a sports bar, or a grad school coffee shop (especially if the grad school is heavier on male enrollment, with programs in engineering, computer science, and business). So many girls/women put the man first and neglect themselves. Don't ask about her past relationships, her divorce, her ex or anything else too personal. These people claim to have joined said dating site on a lark (my friend suggested it and I figured why not?). Today's weather was [insert how as the weather like], right? It makes you look bad. Don't construct a fantasy after two dates. Her kids come first. Never put yourself in a compromising situation--most people are trustworthy, but date rape is unfortunately a real occurrence. Don't try too hard to make the guy like you. Think about your decision.