Guest Contribution: 4 Ways to Get a Second Date

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Getting back into the dating game can be rough if you’ve been out of it for a few years (or decades). Maybe you once considered yourself a Romeo, but now you’re out of practice and not sure how to proceed. Plus, you know the dating rules have changed since the last time you were on the market. So how do you make sure you score a second date with a nice woman, next time someone piques your interest? Here are four ways.

1. Don’t Come on Too Strong

Many men who re-enter the dating scene again after a long break make the mistake of coming on too strong and scaring the woman away. She may be beautiful and amazing, but don’t keep telling her so over and over again. This will put you in “potential creepy stalker” territory in her mind right away. In addition, avoid:

  • telling her you could fall in love with her
  • planning a date that is too extravagant or too romantic
  • kissing her too deeply and too long when you say goodnight
  • lavishing her with overly expensive gifts

Instead, be polite, alert, and give her a small gift at the beginning of the date, or even before. Consider having flowers delivered to her office the day of your date to show her that you’re looking forward to the evening ahead.

2. Be a Good Listener

Another mistake men make on first dates is talking too much about themselves. While she does want to know certain things about you, she also wants you to know about her, and she wants to see if you’re a good listener. Make sure the conversation is two-sided and ask plenty of questions about her childhood, family, job, and hobbies.

3. Keep the Conversation Light

There’s an old saying that you should never talk about religion or politics in polite company. The same is true for a first date. Avoid discussing anything that could lead to potential arguments. Now is also not the time to talk about things that are too intimate, such as your most recent colonoscopy or your ex-wife’s cheating ways. Keep the conversation topics light and positive to make way for enjoyable conversation.

4. Pay for the Date

It may sound old-fashioned, but most of today’s women still expect the man to pay for the first date. Going Dutch on subsequent dates is perfectly okay, and if she really likes you, she may even offer to pay on future dates. However, you won’t get any future dates with her if you don’t pay for the first. Lack of paying shows a lack of consideration and general lack of manners on your part. Make her feel like a lady, and insist on treating her to a nice meal on your first date.