Dating and Relationship Advice – Dating Etiquette and Rules for Women – First & Second Dates

“Ladies! Here’s a complete roadmap to dating etiquette!”

It’s been a great night of drinks, dinner, and conversation, but the evening is coming to a close as the bill is finally brought to the table. Questions start to flood your mind: Do I offer to pay? Did I do everything I could have to impress my date? Will there be a second date?

Dates can be stressful, especially first dates, but by following some dating etiquette, a woman can relax and enjoy the experience. Here are some guidelines to help you handle awkward situations involving the bill, and some other general dating advice for women.

How to Handle the Financial Aspect of Dating

Who should pay the bill when you go out on a date? What can you order on the date? It all depends on how long you’ve been dating, and how far you are into the relationship. The financial aspect of dating is much different for a first date, for example, than it is for a fourth or fifth date.

First Dates

Most men will pay for first dates, but some won’t pay or expect the woman to pay for her share. Here is some advice for a woman going on a first date:

  1. Go Prepared. Even if the man asked you out by offering to pay for your dinner, bring enough money to pay. The man may forget his wallet, or be unable to fully cover the bill. Perhaps he intended to split the bill from the beginning. Or maybe the date just doesn’t go well, and he no longer wants to pay for your share. With so many possibilities, it’s a good idea to carry cash with you and be prepared to take care of the bill if necessary.
  2. Be Considerate of What You Order. A first date is not the time to order the most expensive item on the menu, or to order multiple courses and pricey drinks. By the end of the date, you may quickly decide that the guy is not right for you. It would be inappropriate to let him know you are not interested, after he just spent half his paycheck on you.
  3. Be Mindful of the Restaurant You Pick. If the man asks you to pick the restaurant, choose a moderately priced restaurant or find restuarant discounts and coupons. Don’t select an expensive restaurant, and don’t ask to go to a fast food restaurant, either. You do not want the man to have to pay for an expensive dinner, and you do not want to insult him by selecting a cheap restaurant.
  4. Subtly Offer to Pay. While most men will pay, it is important to make sure that the man knows you did not just go on the date for a free dinner. Some men will be insulted if you offer to pay, so you need to subtly hint that you are willing to pay. For instance, when the check comes to the table, reach for your purse. Chances are that the man will tell you not to worry about it as he reaches for his wallet. Just thank him, and let him know that you appreciate his gesture. If he doesn’t stop you, don’t be offended. Simply offer to split the bill, which is fair.

Subsequent Dates

Ladies, after you have been on your first date or two with a man, the rules change a little. Do not expect the man to continue to pay for nice dinners and evenings out, even though some men will still pay. Here is some advice as your dating relationship gets more serious:

  1. Continue to Offer to Pay. You always want to arrive prepared, and if this is your second, third, or fourth date, the man may or may not allow you to pay, but at least you have shown that you are willing. It all depends on his belief system, how he was raised, and his current financial situation. If you find out that your personal belief system about how men and women should split the bills on dates doesn’t match with his, perhaps this is where the relationship ends.
  2. Communicate. If you continue to date this gentleman, there may be a time when you feel it is right to discuss the financial aspect of dates. A conversation about how bills are split on dates helps both of you to understand what to expect. If this is going to be a lasting relationship, this may be the first of many difficult conversations about finances, and it is important to open the lines of communication from the very beginning.
  3. Do What Works as a Couple. In this modern era of working women, there are a lot more options when it comes to paying for a date. Essentially, it’s about what works best for each individual couple. Perhaps you decide to take turns paying, or perhaps the man decides he always wants to pay. The key is to communicate about money, so that there are no hard feelings.

General Dating Etiquette for Women

Although the financial aspect of dating has changed drastically in recent decades, it is just one aspect of dating etiquette. Here is some more general etiquette advice for women going out on dates:

  1. Give Him a Chance. You may have had a long week at work, and you may be tired of the dating scene, but if you have agreed to go out on a date, you need to put your best foot forward. The man you are going out with may have been looking forward to this date all week, and perhaps had to step out of his comfort zone to ask you out. Have a good attitude and an open mind while you are on the date.  You could end up having the night of your life.
  2. Dress to Impress. You may not feel like dressing up or trying to impress your date, but he may be expecting more than jeans and an old t-shirt. If a man is buying you a nice dinner or dressing up for you, show your appreciation by freshening up before you go on your date. It’s a nice gesture, especially since men really enjoy seeing the woman they are taking out all dressed up.
  3. Arrive on Time. Unfortunately, women are known for being late. Show your date respect by arriving on time. If you know you will be running behind, call ahead or text to let your date know. That way, he’s not wondering if you have bailed.
  4. Don’t Talk About Old Relationships. There is no bigger turnoff than a woman talking about her old boyfriends. If you say something positive about an old boyfriend, it shows that you admire him and may still have feelings for him. On the other hand, if you say something negative, how does your date know that you won’t do the same to him?
  5. Don’t Dominate the Conversation. Another turnoff is when someone dominates the conversation, so make sure you give the man a chance to talk about himself. That is also the only way you will get to know him.
  6. Don’t Talk About Marriage or Children. If you talk about marriage or children, you may come off as too desperate, and it may scare your date away. Show your date some respect by avoiding a pushy subject, such as marriage, too early in your relationship.
  7. Don’t Drink Too Much. First of all, if the man is paying, he will pay for all your drinks, which will quickly add up on the bill. Secondly, you don’t want to come off as though you have a drinking problem, which may be a red flag for the man. Most importantly, you need to make sure you are thinking straight. If you are out on a first date with a man you do not know, you do not want to make yourself vulnerable by having too much to drink.
  8. Be Interested in Him. You may not find his profession as an accountant or computer programmer riveting, but make eye contact and show him that you are interested in what he has to say. Hopefully he will show the same respect for you.
  9. Don’t Play Games. It takes courage for a man to step out of his comfort zone and ask out a woman, so be honest and straightforward with him. Don’t play games by acting as though you are interested in him, or not interested in him.
  10. Don’t Chase Him. Don’t rush the relationship or try to move along the relationship at an uncomfortable pace. Let the man be the pursuer, and wait for him to contact you. Women are sometimes ready to express their feelings much earlier in their relationships than men are, so don’t pressure him to express his feelings prematurely.
  11. Be Honest. Don’t give the guy the runaround if you know it is not going to work out, and don’t avoid the subject of a second date if you need to tell him that you won’t be going on one. Be honest, and do it at the end of the first date or soon after. That way, he doesn’t get his hopes up and expect a second date.
  12. End the Date if Necessary. If the date is going on too long, and you are ready to go home, it’s okay if you end the date. Just say that you are ready to call it a night. If you do not plan on going on a second date, don’t hint that a second date is a possibility. There is no reason to carry on the date through coffee and dessert if it is miserable and not going anywhere. Your date may appreciate your honesty, and the end to a rough night.

Final Word

The most important piece of dating etiquette for a woman is to be respectful of the man you are dating. Be respectful of how you treat him, and be respectful of his wallet if he’s paying. If you respect him, he will respect you, and hopefully that will lead to a long and happy relationship together, lasting much longer than a few dinner dates!


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17 thoughts on “Dating and Relationship Advice – Dating Etiquette and Rules for Women – First & Second Dates”

  1. A few thoughts from moi. I haven’t covered everything.

    I always try to just be myself. It’s always been a selling point for me. If you have to overly impress someone on a first date, at some point further down the link you’re going to get rumbled.

    I go into any date as if I’m just meeting a friend for dinner. If you are instantly thinking about them as a potential partner you are letting yourself in for all sorts of awkwardness. Look at them as a person first and ‘whatever’ material later.

    I never over dress because I always look and feel so awkward. Of course it depends on where you are going and what you’re doing.

    I don’t mention ex’s or current partners unless he does. Sometimes it’s actually a part of the dating territory for me but if that’s the case those subjects have already been broached before in texts.

    If he talks about marriage or children I will get up and leave. Never happening. I can’t imagine a less sexy subject for a first date or any date.

  2. Nice to hear your perspective. Sound advice. Of course, with all things you sometimes just have to roll with it. For example, it seemed like guys would always ask “ so how many dates have you gone on with someone online?” which always open up the can of worms of bad dates! Totally agree about not hinting or going along with suggestions of a second date if you have no intention of going!

    1. I agree that so many ask about dating history. It is uncomfortable when that is the first topic brought up. How long have you been on the dating site? Any luck on the sites? etc. I get asked things like this all the time. So tired of dating.

      1. forgive me but I do like hearing about how it’s not going well on the dating site and it’s going amazing on my date! 🙂 See: Cherie – First Date

  3. Some great pointers here!!
    I personally have always discussed finances before the date, a little crass I know but I have strong beliefs of paying my share and don’t want things to end up awkward when it comes to paying the check. If a man somehow feels demasculated by me paying my share of the check then he is not for me and we probably should not go on the date anyway.

  4. Thank you so much for this post. So much of this advice goes both ways. .I am always on time- 10 minutes early actually. I don’t know how often my date is late. They tend to talk about dating, their ex-wives, etc way too much. I had one guy ask me out for a second date but I told him that I couldn’t because he was obviously still in love with his ex-wife. he dais yes he was but it was over. Wow.
    The money advice was awesome. When I first started dating four years ago, I had no idea how to handle it. It has gotten easier. I always offer to pay my share on first dates but most men don’t accept. I do wish they would clarify prior to a date if they want dutch though. It doesn’t affect my choices but will better prepare me.

    1. You’re welcome. It’s really time for this. I told so many stories in 2016 and 2017 and just felt like it was time to open the conversation about dating etiquette. Now more than ever in the texting and online dating age is it needed. I come from a time when you courted a lady. I hear from so many women nowadays that young men suck and have no game. It’s sad. Romance is so beautiful and such an integral part of meeting someone. It’s really the most fun and elegant part until the hopefully intimate union. But I feel like today it’s lost. There is a series coming up soon in this blog where I fell in love and we actually sent love letters to each other for a year after our meeting. Ancient by today’s standards, but I wouldn’t change it or the world. The anticipation and joy of getting the perfumed letter in the mail. Glorious!

      1. I am always hungry. I walk over 10 miles a day but I would never go out with a man just for that.

  5. It’s been well over 36 years since I was in the dating scene, and that is because the love of my life was with me for 29 years and I have had casual, if platonic, friendships for the past seven. Any dates I might go on, in the future, would certainly reflect the changes in this world, since 1982. I will say, though, that my dinner or lunch conversations with women friends have been wide-ranging and our time spent together has seen a variety of activities, all with the aim of friendship.

What are your thoughts on this subject?