The period of time after you break up with your ex can feel a little like squeezing in between a rock and a hard place. A phase of your life is over, but you're not dead. You want to get out and meet someone new, but by the same token, it may have been years – even a lot of years – since you last took a woman on a date. The good news is that it's perfectly OK if you feel feel a little out of your depth. Admitting it can even be endearing and break the ice. You'll want to follow a few rules too, however.
Remember Your Manners
Chivalry is not dead, and it never was. Women go a little soft inside when a man holds doors, pulls out chairs – and yes, pays for the date. Even if she's the independent sort and insists on chipping in, she'll appreciate that you tried. Don't overdo it. Showing up at her door with a dozen red roses on your first date is probably overkill. You'll score points if your politeness and consideration extends to others as well, such as the waitress or the guy taking your tickets at the movie theater.
It's All About Her
You know better than to talk endlessly about your ex, but going on and on about your job, your kids or even your dog is a no-no too. Make the conversation about your date. Ask her questions; find out how she feels about things. If she asks about you, of course you should respond, but don't monopolize the conversation. It might suggest that you don't care how she feels or what she thinks. Whatever the two of you talk about, give it your full attention. This means ignoring cellphone calls or text messages unless they’re urgent.
Hold the Liquor
If you're old enough to be worried about dating again after a long time spent with one woman, you're old enough to know how much liquor you can reasonably hold. Don't cross the line. If you go out for dinner, sharing a bottle of wine is great. Capping it off with three shots of whiskey so she has to worry about getting in the car with you afterward is not so good. An added risk is that you might find yourself blathering on about your ex, despite your best intentions, if you drink too much.
The Next Level
After you have one or two successful dates under your belt, you might start feeling like a real Romeo. You're naturally eager to take things to the next level physically. This is where you have to be at least reasonably perceptive. When and if she's interested, she'll let you know. The signs may be subtle, but they'll probably be there. It may be the way she leans toward you when you speak, or it might be more overt, like a hand on your arm or your thigh as she laughs at one of your jokes. You probably don't want to push things until she begins throwing off these signals.
If She's Not the One
In the years that have passed since you were last single, you may have forgotten that you're not going to hit a home run every time you go up to bat. It's possible you'll decide that the first woman you date – or the second or third – is not really someone you want to see again. That's fine, but be honest with her. Don't tell her you're going to call again if you know you won't. Thank her for a wonderful evening and be done with it. If nothing else, you have a little more experience under your belt now, so all isn't lost.