There has been a recurring theme in the comments of my past articles. Many people seem to be doing well getting the first date, but for some reason, can’t seem to get a second date and want to know why. This article will focus on a few things guys and girls can do to have fun, express interest and get that second date.

Tips for Men:

1)      Express genuine interest. Make sure you are in the seat facing the wall, not facing the main part of the restaurant or bar. This will allow you to focus your attention on her and not be distracted by anybody walking behind her. Listen intently to everything she says. Nod your head in agreement if she says something you like.

2)      Compliment something, but don’t overdo it. Instead of saying “You are so beautiful,” say “I really like your sweater.” Make sure the compliment is sincere and don’t repeat the compliment again. A well-placed, honest compliment will go far.

3)      Let her speak more about herself than you do about yourself. People tend to think they know the other person better than they actually do when they are allowed to speak at length about themselves. I know it sounds strange, but try it on your next date. Speak less, listen more.

4)      Test the waters. If she says that she likes baseball, perhaps respond by saying “Maybe we could go to a game next week.” You are probing her feelings and can learn a lot about how she feels by her response.

5)      Make sure you pay. A guy should pay for the first few dates in a new relationship. Be a gentleman and do the right thing. Even if she offers to split the bill, don’t let her.

6)      Express your interest. At the end of the date, tell her that you would like to see her again. However, if you have no intention of calling, you must never say, “I will call you.” That is a cardinal sin. If you have no interest, just thank her for a nice evening and say goodbye. It will lead to fewer problems going forward when she expects to hear from you.

Tips for Women:

1)      Be yourself. Don’t only order a salad if you are hungry. Guys hate that. If you are hungry, feel free to order whatever you want. Relax and have fun.

2)      Don’t ask how much money he makes. This is a total turnoff for a guy. It is irrelevant at this stage and, more importantly, none of your business.

3)      Don’t talk about or compare ex-boyfriends. Not verbally or mentally. Not at all. Every guy is different and it isn’t fair to compare a guy to somebody else while on a date with a new guy.

4)      Test the waters. Yes, a girl can also suggest doing something with her date the following week to see how he responds.

5)      Don’t ask the guy out at the end of the date. Instead, tell him you had a nice time and see how he reacts. Take control of the end of the date and put the ball in his court. If he asks you out again, great. If not, move on. There are plenty of other guys out there ready to go out with you.

I appreciate all of the comments and emails I have been getting over the past few months. Should there be a topic you would like me to write about in the future, please let me know. I look forward to hearing from you.

After being a bachelor for many years and counseling his friends about dating, Brad Berkowitz, who is now a JDate Success Story, decided to write the book, The 21st Century Guide to Bachelorhood: Lessons Learned Over 20 Years, to help other men navigate the dating scene. To purchase the book, click here! For more articles by Brad, click here.
  1. I have had awkard dates with guys asking me out at lunchtime or dinner time, and then not generously offering to take me to eat, but staying in my company for 2-4 hours. These guys have boasted about how much they make. It is weird and humiliating.

  2. My question to you concerns online dating ettiquette. I have been advised so many different ways to getting a gentleman’s attention to let him know that you are interested. But, none of the advice that I have been told or read is working. Who should contact who first online, the guy or the girl? Or how do you get his attention without looking desparate or aggressive? When guys ask for your phone number and then he does’nt call, what’s up with that? I don’t get it! Please advise the right steps to take.
    All Smiles,

  3. Comment-I disagree with your advice, on letting a woman know after the first date, that your interested and would it be OK if I call you. At this point you don’t want to put her on the spot either. It creates an awkward moment and it may cause her to lie so as not to hurt your feelings. All dates should be left with a ‘thank you for coming out and meeting me’ or ‘it was nice to meet you.’ If you’re interested, you can send her an email thanking her again and letting her know you are interested in seeing her again. If she’s not interested, she will let you know.

  4. Women always tell me that they want to know that the guy is interested. Guys play too many game. Emailing that you had a good time is nice, but you have to follow that with a call, and not a week later. Call within 2 days and ask her out again. The longer you wait, the less interested she thinks you are.

  5. Betty,

    Many guys take numbers and don’t call. Sometimes they feel obligated since you have been in conversation for a while. Sometimes they have had a few drinks and are in “number-gathering” mode. If a guy doesn’t call, he isn’t interested. I am amazed how many women just don’t understand that.

    You can feel free to contact a guy first. Don’t ask him out. Maybe compliment something in his profile or photo. Let him get back to you and ask you out.

  6. Guys, if you follow his advice you’ll end up in “the friend zone.” If you want a second, third, 4th date, you need to do the following:

    1. Be funny. Nothing endears a woman to you than if you can make her laugh. Make fun of her shirt, her hair, her purse, whatever. Don’t be mean – be cute. If she has a leopard print scarf, ask her what happened to the rest of the leopard. Simple, funny teasing.

    2. Don’t be “question guy”. Yes it’s the first date. No, you don’t know each other well. That doesn’t mean the first date is supposed to be an interrogation. Nothing saps romance like “So what do you do for fun, what was the last movie you saw, are you having a good time, what’s your favorite type of food?” and so on. It’s boring, one way conversation. Balance questions with anecdotes. Besides, if you have to ask so many questions on the first date, you didn’t lay enough groundwork prior to meeting her.

    3. Touch her. Not in some creepy groping way, but casual, polite touching – her hand to look at a ring, her back when you want to bring her closer to “tell her something secret”, etc. It has to be casual and natural – if she sees it coming she’ll recoil.

    4. Don’t pay. It’s 2010. Chivalry isn’t dead, but she’s not a present and you’re not buying her. You both chose to meet, and unless it’s less than $10, she should pay her share. Women respect men who are confident enough in their masculinity to let a woman pay.

    Women –

    1. Relax. It’s a date – not your wedding night. Nothing gets a guy more nervious than a woman who’s projecting the same emotions. Calm down, see it for what it is – a date. Lower your expectations and allow yourself to enjoy the date.

    2. Ask him about his hobbies. Men, like women, like to talk about themselves – but more about what they do and like than who they are. If a man isn’t opening up at first, the second you show interest in his hobbies/work, he won’t shut up about them. If he has no hobbies though, be careful, the man may be a workaholic.

    3. Kiss him if you want to. If a man likes you, he’s going to try to (or should) kiss you. If you want to, do it. He’s not going to lose respect for you or thing you’re “easy”. It’s a kiss, you’re not hopping into bed with him. If a man goes for the kiss and you reject him, that’s it. He won’t call, e-mail, or text. If you’re following some personal or perceived rule about not kissing on the first date, you probably won’t find confident, assertive men, you’ll likely find doormats waiting for your approval.

  7. It is obvious why Dan is single and dateless. I know him and he is a moron. Chivalry is not dead. A guy, if he asks out the girl, should always pay. The girl should offer to pay, but the guy should pay.

    His other advice is obvious and it’s obvious why he is the one in the friend zone.

  8. Larry is right. A guy should pay, but I always offer. A guy will be seen as cheap. BUT, one point that Dateless Dan should realize and I think does is that a guy is not a cash machine and should not be taken advantage of. The guy should not pay all the time or Dateless Dan will be correct, he will be the friend.

  9. none of this s*** works. it doesn’t matter, it’s a total crapshoot and you can’t control the outcome. Seems dating is just like sales, to get a second date go out on 1,000 first dates, which MIGHT land you 10 2nd dates, and one of those Might land you a third. I don’t care if you’re brad pitt, that’s how it seems to work (in the U.S. at least). She has a million reasons why shy either won’t be interested or freak out and go back into her hole (even if you’re Brad Pitt, trust me). you can do all the above advice, which doesn’t hurt, but chances are you have to go through thousands of women to find one you MUTUALLY connect with. So get to it! or be smarter than the rest of us and transcend relationships alltogether (monkhood?)

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