If you have no problem landing dates but rarely get repeats, it’s probably something you did. When enjoying a date, don’t get too comfortable. Sarah Jacobsson Purewal of Men’s Health shares some reminders.

  1. Don’t think that because it’s the 21st century, you can wait for her to make the first move. She might, but then again, she might not. Women fight for their rights, yes, but it’s not always the same when it comes to dating and courtship. Dating Coach JT Tran says, girls are still girls at heart, and a guy making the first move isn’t at all against their ideas of women’s liberalization.
  2. On the first few dates, pick up the tab. Gender equality is a convenient way to spare your wallet, but picking up the tab creates the impression that you’re financially stable. The concept of modern women being offended by the male’s masculine take-charge role is often exaggerated. Pay the bill, at least on the first few dates.
  3. When you find yourself dating the same woman for a fourth time, allow her to pick up the tab if she offers. Don’t feel like you need to pay for everything. Once you’ve found a comfortable ground for both of you, it’s also time to set equal footing; that includes paying the bill.
  4. Allow her to discover you; don’t tick off your MBAs and work experiences like you offer your resume to a potential employer. It doesn’t mean that you stop talking about yourself. Men often think that their value as a person depends on what they’ve accomplished and what they do for a living. Women, on the other hand, think more about how a man views things and ideas, what moves him, and how he responds to other people.
  5. Plan your date and make it something that she can smile about. A well-planned date shows that you’re a decisive person. Planning a day for the date is a level above an ordinary dinner date, for instance. It makes the date day an opportunity to discover each other under different settings. It also helps you decide whether the two of you click.
  6. Don’t scare her off with too many plans. You can’t date her today for the first time, and ask her to a Christmas holiday with your family on the second. Unless you’ve been dating her exclusively for a while, don’t think she’ll be tickled with plans several months in the future. Relationship expert Anita Chlipala says that dates should help you learn about each other, not put unnecessary pressure on the relationship.
  7. Don’t be a phony. The real you may not be all that attractive, but neither is the mask you’re wearing. Besides, it’s not only her you’re fooling, you’re fooling yourself as well. If she does find your put-on likeable, you can’t pretend forever. Instead, enhance your good traits to offset any of your defects. Your date may even find your flaws charming, so get real!
  8. If you can avoid it, don’t date a co-worker. It does happen often, for reasons that are usually work-related. You’re attracted to a colleague because you share similar conditions, or you find affinity with her because you’re both fuelled with the same excitement and goals. There’s nothing wrong with either of those attractions, except that you shouldn’t date a person for the wrong reasons. If you can’t help it, take a date with her away from the office. See if you still find her attractive, minus work-related stimuli. Talk about the world, your personal lives, and views. And, hey, don’t talk shop.
  9. Don’t think that women all fit in one category, because they belong to more categories than you can imagine. It’s safe to think that on one end of the spectrum are women who prefer doting men, and on the other are women who are scared of elaborate attention from men. In between are categories with assorted preferences, fears, ideals, and a good dose of whims. The important note then, is: don’t shower her with superfluity on the first date. Observe what kind of person she is before you decide to invite her to an exclusive rooftop dinner with an orchestra playing. If she’s not of the same commitment level you are, she’ll start looking for the exit door.
  10. Be truly interested in her. Men seldom ask women how they feel. At best they ask, “What’s wrong?” If there’s something more important than asking your date how she is, it’s listening to what she has to say. Be prepared to listen about her detailed account, because women love to recount. If you find her stories boring, if your mind drifts when she talks, start rethinking about your relationship.
  11. When you’re on a date, be mentally present. Texting other people is rude.
  12. Don’t read too much into women’s words and actions. There are times when a woman’s statements should be read between the lines. Over-analysing her every word, however, results in finding negative meanings every way you turn, and it is counterproductive.
  13. Know when to give up, but not on the first try. Sales expert and author Grant Cardone says that you must be confident and resourceful when pursuing a girl, pretty much like pursuing a multi-million dollar account. Don’t sound or look desperate, either. If one approach proves to be an epic fail, be creative. A guy must be innovative in landing a date, not make twenty similar attempts at inviting her to dinner. That’s desperate!
  14. Pipe up about your feelings. If you’ve been friends with her for quite some time and you want to explore the higher level, tell her so in no uncertain terms. There’s no reason you should hide behind your friendship. Your thoughts and feelings may or may not align with hers, but she will respect you for speaking up.
  15. There’s no perfect woman, so don’t wait for her. Worse, don’t look for her in your date. Chlipala says that women, like men, have flaws and imperfections. If her desirable qualities offset her less attractive traits and you feel something special for her, those are good reasons for you to make a go of it.

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Dating is a fun way to learn about a woman you’re courting, and about the guy that you are. More than the fun, psychologist Tracy Thomas, Ph.D. says that the first few dates influence the kind of relationship you’ll eventually develop with her. Casual dates aren’t as random and as careless as they seem, after all.