Whether you are a serial dater or haven’t been out there in 20 years, these tips will help you no matter what. So dig in, and brush up on your swagger!

  1. If you have kids, you will find that it’s much easier to date someone who also has kids. No one understands the challenges of a single parent like another single parent. They just “get it.” That said, don’t talk all night about your kids, this is your time to shine as an individual, and a potential partner.
  2. Unless you’ve had a lot of conversations with someone online, or have met them in person and felt a bit of “chemistry,” don’t take them to dinner for a first date. It makes a very long evening if you meet someone for the first time and either A) they look NOTHING like their profile pic, or B) you discover very early on that there is no way in hell it’s going to work and you just want the night to end already.
  3. Meet them already! If you have been chatting with someone online and it’s going well, meet them as soon as you can. Sometimes you can chat with someone for months before meeting them, only to find that even though you really like them in person as well as online, there is just no spark, or chemistry, and it’s just not going to get there. Alternately, some of the best dates come from the ones that you reject early on in the conversation as “not my type,” only to find out that in person, there is an undeniable chemistry.
  4. Be yourself. Chances are she is just as uncomfortable and nervous as you are, and being yourself will be the fastest way to unsettle both of you and find out if you are a good match. It’s likely that if you can take the lead and make her feel comfortable, it will relieve some anxiety for both of you and she will open up and be herself, too.
  5. Don’t bitch about your ex, and don’t call your ex a bitch. It’s a huge turn-off for a woman. You come across as bitter, angry and “just not over it.” No one likes a complainer, or a man who is disrespectful towards women.
  6. Don’t tell her you hate your job, even if you do. There is nothing a woman likes less than a man who isn’t happy, and likely comes home from work grumpy every night. It also makes you look weak, staying in a job you hate. Women want a man who is generally happy, and loves what they do. It doesn’t matter what your job is, they would rather see you be happy with a lower wage-earning job that you love than in a higher paying job that you hate.
  7. Don’t talk about money. If you have a lot, don’t brag about it, if you’re broke, don’t complain about it. Same can be said for politics and religion. Just avoid the topics altogether. These conversations often lead to heated debates and the “fun” is gone.
  8. Dress up a bit! Don’t show up in grubby clothes and running shoes; show her that you give a crap about yourself and how you look. Let her know that you are able to look after yourself, and that you feel she is important enough to look decent for.
  9. Balance the conversation. Don’t take over and make it about yourself all night. Sure, she’s there to get to know you, but make sure you let her know that you want to get to know her, too. Ask her questions about herself and pay attention.
  10. Don’t “one-up” her all night. There is nothing worse than opening up and getting to know someone and every story you tell them, you get cut off while they make it about them and how the same thing happened to themselves, but their story was much more dramatic than yours. If you do have the same story, but yours is “10 times better than hers,” save it for another time, or at the very least, don’t do it more than once. She will appreciate it.
  11. Put your damn phone down! This is a big one guys. Most women will admit that when a first date answers their phone outside of an emergency, or even worse, is texting during the evening, that’s a huge deal breaker.
  12. Don’t make it about sex unless you’ve already had the conversation and determined that that’s what you’re both there for. Steer clear of the conversation in general unless she leads it, and even then, don’t take it any further than she does. You can flirt and it can be sexy, it doesn’t have to be about sex, and if you start talking sex before she does, she is probably looking to book it and get out of there.
  13. Don’t go to her house and don’t invite her to yours. It automatically gives one of you an unfair advantage and can be very uncomfortable for the person who doesn’t live there. Go somewhere neutral, where you are both meeting on an even playing field.
  14. Plan something easy and fun. Even if it’s grabbing a coffee and heading to the lake for a walk. She will appreciate that you take care of the details and she knows the plan in advance so she can dress accordingly. It’s way better than getting into the old “I don’t know, what do you want to do?” scenario. 
  15. Don’t take it too seriously. You’re meeting her for the first time. Think of it as meeting a new friend, or basic networking. Sure it has the potential to be more, but so does meeting anyone, anywhere for the first time.
  16. If you’re a sports nut, and she isn’t, don’t talk about it all night. Women have nightmares envisioning lonely evenings with the TV being hijacked by “he shoots… he scores” night after night.
  17. Pick up the tab. If she is insistent on “splitting the bill,” suggest that she gets the next one. If you are really strapped for cash, go for a coffee. Do something you can afford, but pick up the tab. If she gets really demanding, let her split it, but only when you see she won’t take no for an answer.
  18. If you discover early on that you like her, let her know it by suggesting you go to see a movie or do something together based on the conversation so far. Planning the next date early on if you like her will cut the tension and you’ll probably both have a much better time.
  19. Send her a cute text after she leaves (preferably within the hour) if you want to see her again. Nothing crazy, a simple, “thanks for a great evening, look forward to seeing you again” will score you huge points if she is interested as well.
  20. Offer to pick her up for the date. Most women today will opt to drive to and from a first date for safety reasons, but offer anyway. It’s still a nice gesture that will be appreciated.
  21. Finally… Consider this: No date is a bad date. Get over it. You got out of the house, you met someone, tried something different. Hopefully you had a decent conversation, maybe a glass of wine or a cold beer, and whether it’s going to lead to a second date or not doesn’t really matter. Good for you, you’ve got another life story, good or bad. Man up and move on to the next.

 

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