Avoid Costly Dates
On early dates, stay away from outings that result in hefty bills, even if you have deep enough pockets for it. You do not want your date getting the sense that you are trying to win her over with your money. Additionally, she may insist on paying half of the costs herself, so even if you can afford it easily, she may not have that same luxury. Stick to modest environments and give yourself a chance to connect without interference from your wallet.
Set Early Evening Dates
Patti Novak, dating expert and hostess of the show "Confessions of a Matchmaker," recommends picking early evening starting times for your dates with someone new. This gives you ample opportunity to stretch the date out late into the night if you enjoy each other's company. An early evening date is better than the informal setting of lunch. A breakfast date is typically not a good time, as people are often rushed in the morning or have their mind already set on the day of work ahead.
Choose Safe Settings
Until you and your new date become more comfortable with each other, stick to public environments in which both of you feel secure. Avoid having dinner dates alone at the other's house; not only does this create a very formal atmosphere that adds pressure to the event, it also poses a safety risk for the guest who does not know his date well yet. Similarly, a loud and active setting like a rock concert may prove unnerving for some and is not an ideal environment to get to know each other.
Don't Talk About Ex-Relationships
While it's important to show honesty about your past relationships, the first few dates with someone new is not the time to do it. If you spend too much time discussing your ex, your date might draw the conclusion that you still have feelings for her. A useful thing to bear in mind when first dating someone is that if you are overly tempted to talk about your last relationship, you are likely not ready to get back into the dating game.