The 5280 Singles Official Rules of Dating Handbook (Copyright 2016)
So many things are constantly changing the landscape of dating, that we decided to write down some tried and true approaches that have worked throughout generations and adapt them to modern society, technology and our ever changing world in order to help many singles have a grasp on how people who are dating can or should conduct themselves. We will cover many topics and add comments from either a man’s point of view or a women’s perspective about the topic or suggestion. To keep it brief we will keep the comments limited in scope to stay focused on dating protocol and etiquette recommended for the 21st century dating single.
Asking a person out.
It is completely acceptable for a woman to ask a man or a man to ask a woman out for a date if they are reasonably well acquainted. We will apply the fairness doctrine and state that the person doing the asking should be prepared to pay for the first date.
He said: I try to only ask women out that I have known for a period of time. When I do, I try to make the first date pretty low key, inexpensive or simple so as not to put a lot of pressure on the date itself.
She said: I don’t usually ask a guy out. I would like it better if some of my first dates were to be more impressive, but I can understand many of the complexities of someone trying to succeed in just getting me to go out on a date with them.
Rule #1
Don’t ever ask out a family member or married individual, it never really works out. Don’t accept a date with one either.
Rule #2
Use extreme caution when asking a co-worker or client out. It could significantly impact or affect your job or career.
Rule #3
Consider all the positives and negatives for a person to say yes to your date request, before making the approach to ask them out.
Rule #4
No matter how impossible it is, try to make the environment extremely user friendly, around the asking of the first date.
Rule #5
Don’t ask the same person out more than 3 times, unless they have given their approval for you to keep trying until the time is right.
Rule #6
Avoid at all costs using technology to ask someone out. In person is the best, phone requests are okay, but texting or emailing can be perceived as lame and noncommittal. Besides don’t you want to see for yourself if there is a positive reaction to the prospect of dating you?
Rule #7
Never cancel a first date via text or email. It sends the wrong message about you or the circumstance. Call them if the situation permits.
Rule # 8
Set boundaries up for the first date. Items like how expensive, who will pay for what, where to meet and how much time to allow for the date.
Rule #9
If you are online dating, using an app or going on a date that has been set up for you, please only agree to meet in a public place for everyone’s safety. This includes not traveling together later to a place where you may be completely alone with someone you may barely know.
Rule #10
Always keep an open mind towards the person you are meeting for a first date. Remember, dates can lead to making important contacts, making new friends or leading to a lasting relationship. These can all be acceptable outcomes. Sometimes a first date can be an easy example of why two people should not be dating each other, but it can be okay to have a little fun with that reality and end the night on good terms. It is conceivable you may run into this person in the future, so try not to scar your date for life.
The First Date
Rule #11
Do everything within your abilities to not be late for your first date. You only get one chance to make a good first impression.
He said: I once had to wait over an hour to meet a lady for a dinner date. It caused me to lose our reservation as well as made me wonder if I should even be dating this person.
She said: Sometimes I have to do something more than once to prepare for a date, so I hope he can wait at least a few minutes if I run late. That being said, when I am ready and waiting for a date to pick me up, I don’t like waiting more than 15 minutes for him to arrive.
Rule #12
Make sure there is room in your date for at least an hour of getting to know a little about each other or talk about things you may have in common.
Rule #13
Leave exes out of the conversation! You can mention you were married once or came close a time or two, but do not reveal your failures in marriage on the first date. This includes issues with past relationships, too.
Rule #14
Acceptable topics of discussion: Nearly everything except past relationships, family drama, politics or specifics on religion.
Rule #15
Dress similarly or appropriately. Conferring with each other if this is a casual dress date or dressing up is fine. Try not to out dress your date severely or embarrass them.
Rule #16
Do not check out members of the opposite sex while you are on a date. This is extremely rude and disrespectful to your date. Flirting with or getting phone numbers of potential dating partners is prohibited!
Rule #17
Bring your best listening skills to your first date. This includes good eye contact, positive body language and the ability to understand what your date is actually saying to you.
Rule #18
Do not talk about anyone else you are dating or considering dating. A first date is a mutual free trial period that leads both parties to a possible second date or some kind of friendship or mutually respectful acquaintance.
Rule #19
Go along with the date. Never leave within the first hour of the date. Do not do the cliché actions of a rude dater including having another date set up for later in the evening, someone calling you for some fake type of emergency or leaving to go the bathroom and never coming back.
Rule #20
Do not text or take phone calls especially on a first date. Exceptions can be actual emergencies or single parents checking in with the kids or the sitter.
Paying for the Date
She said: Of course I prefer when the man offers to pay for the entire first date, but I am not afraid to offer to help or in the case of a blind date, pay my fair share.
He said: Dating can get really expensive if you don’t keep tabs on it. I appreciate any help my date is willing and able help with any of the expenses. That being said, if I ask someone out, I will be prepared to pick up the check.
Rule #21
If you are on a blind date or a pre date meeting for getting acquainted with someone you met online, it is a good rule to share the cost of the first date equally when possible.
Rule #22
Don’t date someone just to get a free night out or free dinner.
Rule #23
If you appreciate your date and the first activity they paid for, please reciprocate and offer to take care of an item that comes later in the date. For example. “Thanks for taking care of dinner, I’ll buy our next drink at the club.”
Rule #24
Respect financial boundaries and conditions. If the woman has to pay a lot of money just for a sitter to go out on this night, be respectful and don’t expect her to pay for half of everything. By the same token, if you know about the man who is taking you out is undergoing severe financial challenges, don’t expect him to go overboard trying to impress you.
Rule #25
Expensive shows, travel and gifts. Never expect or accept an expensive gift on the first date. It sends the wrong message to both parties. Traveling together before a being in a committed relationship should lean towards each person paying their fair share, unless one of the participants has some free travel benefits to share.
Rule #26
If you are the man, expect to pay for 50-99% of all dating costs. If you are the woman, take note if you are paying more than 60% of the costs of all your dates. It could suggest that your man is a player with lots of other women in play, he is using you or he will never be willing or able to pull his fair share in a relationship.
Rule #27
Tipping in most restaurants and bars is 20-25%. If you did tip a little light, justify why you rate the service you receive each time by the amount of the tip. Ladies, just because your date didn’t tip 25-30% doesn’t mean he won’t be willing to spend money on you.
Rule #28
Agreeing to pay for the first date does not give your date permission to run up a huge tab. Both parties should always be respectful.
Rule #29
Ladies, please do not dangle tests out for your date on the first date. If you offer to pay for something, do it because you want to, not because you are testing the man. Guys, never try the leaving your wallet at home by accident move.
Rule #30
Please work out any financial arrangements for any expensive dates, especially on the first one so that no one feels like they may have been taken advantage of or there is something expected in return.
End of the First Date
Should you have sex on the first date? NO!
He said: Sometimes I am not sure if my date wants me to give her a good night kiss or just a hug. When I settle for the hug, I am left sometimes wondering if I chose poorly and missed an opportunity for another date.
She said: I usually give off enough signs to let my date know he may kiss me goodnight, (if we haven’t kissed yet). That being said, it usually doesn’t mean I want to make out at the end of the date just because I am looking for a great goodnight kiss.
Rule #31
If your first date has not resulted in any kissing until the end of the date, be sure you have both been comfortable with hand holding, hugging or other non verbal communication before you move in on a goodnight kiss. Don’t get too physical especially if you a dating multiple people currently.
Rule #32
It is okay to set up boundaries or conditions for going on a second date during the first date. If you say you will call them in two days, call them even if it is to set up a more convenient time for a good conversation. A good rule of thumb is to call and follow up within 3 days of the date.
Rule #33
Texting your date to see if they got home okay later is acceptable. Texting them to never call or talk to you again or sexting them is unacceptable behavior. Only in extreme cases would there be an exception to this rule.
Rule #34
One way constant calling or texting after a first date is not a good idea. While we are at it, ghosting someone is rather pathetic. If you are old enough to date, then act like a grown up and respectfully communicate with any people that you date.
Rule #35
Let it marinate. Too often we try to decide during a date if we want to see this person again, threatening to say no if anything is said wrong, incorrectly or doesn’t go very well. It is a first date. If you had a good time or like the person, take several days to decide if you can have a good time again with that person. It is acceptable to take up to three dates to decide if you would like to continue dating someone or take the relationship any further.
Rule #36
Honesty is always the best policy! Don’t lead someone on just to get something from them. Be open and considerate at all times.
Rule #37
Ride the cloud. Just because the date ends, doesn’t mean any of the good feelings have to. It is okay to feel good about a person you just had your first date with even if you have no idea exactly how you think it should go from here.
Rule #38
Do not kiss and tell. Don’t post pictures or comments on social media about your date.
Rule #39
Behave like you have done this before. Discretion is best early on. Let all the positives of the first date lead to more dates or a good friendship.
Rule #40
Make plans for a second date if the first date is a success. If there are circumstances that have come up or feelings that have changed, consider just hanging out with the person you had a great date with.
Successive dates after the first date.
He said: I am so relieved when I get to the start of the second date. Sometimes replaying all of the things we did on the first date can lead me to thinking that the next date is completely up in the air. If we kissed on the first date, I like to start with a simple kiss on the second to assure both of us we still have the same interest in each other.
She said: I admit it is hard for me to hold back any feelings about someone after the first date on whether I think it has a future or not. Unfortunately I often have to feel 100% sure that it is going somewhere to even want to pursue additional dates. I may have to be more patient and see if there is more than I think is there and allow more than one date to tell me if there could be a great friendship or relationship with this person.
Rule #41
Three date rule. Yes some people have a 3 date rule for various reasons. Having sex on or after the third date is the most common. Some people may think they must have sex by the third date or the relationship is going nowhere. Others use it as a measuring stick for the possibility of finding love or getting to know a person much better than the first date or two. Use the three date rule to evaluate how it is going and if there can be more dates. Unless you have completely decided there is no way you wish to continue to see this person, take more dates to make a better decision.
Rule #42
Talk about sex. Acceptable topics include safe sex, sexual history, if you would like to have sex together and any dysfunctions of note.
Rule #43
Dream. In a limited fashion, talk about your dreams and ambitions. Share ideas and common feelings you have for your future and you life. Don’t go into too much detail as it may leave your date out in the cold if they can only go a short distance in your direction.
Rule #44
Don’t make any long range plans that include your date. Long term plans belong within the confines of a long term relationship.
Rule #45
Don’t ask what your date is thinking, unless it involves where to go next. While we are here, don’t ever ask your date something you don’t want to know the answer to or a question that you can’t handle a truthful answer to.
Rule #46
If there are kids involved, please try to keep them out of the budding relationship until it has successfully blown past the three month plateau.
Rule #47
Keep other family members at bay also until you have successfully gone past 3-6 months of successful dating.
Rule #48
Please keep much of your personal life, especially dating off your social media at all times. You can friend your dating partner only if you believe you can be friends if things don’t last.
Rule #49
Don’t rush it! Let things take a rather natural course. The most enjoyable part of a relationship is the first few months, so enjoy it!
Rule #50
Exclusive. You can be exclusive as soon as the second date. Most relationships become exclusive within the first 30-60 days depending on the frequency of dates and contact. Most people want to know they are in an exclusive relationship within the first month or two.
Short Term Dating
Short term dating is usually when dating occurs between the same two people for 3- 6 months or so. This should also mean the two of you were exclusively dating for part of that time.
He Said: When I am dating someone for more than a few months it is usually with the pursuit of love, even if I have on occasionally settled for a relationship of convenience.
She Said: Why do so many men want to get so serious so quickly? The first few months or years they don’t want you to even look at another man. A few years later they may start asking about threesomes and open relationships. We as women like to keep options open for a while until we do know exactly what we want.
Rule #51
Take a close look at the past 3-6 months. If you have a strong interest in continuing dating, then do so. If you have dated for six months and wish to continue, don’t feel obligated that you have to date more than six more months. Putting any additional pressure on a new relationship is unhealthy.
Rule #52
Having Sex. Barring any restrictions physically or from moral and/or religious beliefs, most couples have sex in the first six months. Both parties should use some caution and possibly do some research in this area to make sex a very positive experience.
Rule #53
Love…That four letter word. Feelings of love normally start developing within the first six months of dating. Each party must be emotionally available in order to completely fall in love with another person. Don’t hold back too long on your own feelings of love, because it may simply pass you by. Be familiar with the concepts of infatuation, falling in love with love, loving someone and falling in love with someone. Welcome all stages when you are dating this wonderful person and you should find yourself in a loving relationship, if your partner has done the same.
Rule #54
Commitments. Never make a life changing decision within the first six months. Getting engaged or deciding to live together have virtually no benefit when they are rushed into. Commitments to plan a trip or attend an upcoming show are recommended at this stage of dating. Hopefully practicing safe sex has prevented you from any immediate family planning.
Rule #55
Friends and Family. Now that you may have introduced your main squeeze to friends, family or co-workers, make it a point to spend at least as much time alone with them as you do including them in family or friend functions. It is important to keep the romance alive and the expectations at some distance in the first six months to a year.
Rule #56
Do not put new limitations on your dating partner that were not important or relevant during the initial dating period. If it was normal to see them once or twice a week, continue to do so. Restricting access is rather deflating to the momentum of the relationship as well as other aspects.
Rule #57
Do not let any new dating prospects into your life. Deal with this new relationship to the end of its natural path and do not let other temptations destroy what could be a great future with someone. Remember, the grass always looks greener.
Rule #58
Deal with it. If there are any significant problems developing in this new romance, communicate effectively with your mate to diffuse any conflicts. Just complaining about not liking something doesn’t cut it if you want to give this new relationship an honest effort to succeed.
Rule #59
Be respectful of your mate’s friends and family. Always try to take the high road and avoid any traps that could cause your mate to take sides. If they have many flaws, learn to effectively work around them and be thankful they are not coming back home with you.
Rule #60
Don’t get ahead of yourself. Completing up to six months of dating the same person is hopefully a wonderful experience. Try not to paint your relationship into a corner where you don’t see a bright future ahead. Leave all possibilities and options open in order to give this new relationship any chance to survive. Most relationships end within the first six months. Even new businesses don’t seem to last much longer than that.
Transitioning into a Long Term Relationship
Continuing an exclusive relationship past six months to one year can be a little intimidating. To continue further, transitioning your relationship can be a positive step to keep a great relationship going.
She Said: I sometimes wonder if I like playing house as much as having a significant other to love. I really enjoy having a wonderful man to share many parts of my life with and meet many of my needs. I do sometimes worry when things seem to be going too well and then sometimes I over analyze things and make them seem like they are not as good as they are.
He Said: The couple of times I have gotten into a long term relationship, I worried maybe a little too much about how well this relationship could work over the years, instead of making it work really good in the present.
Rule #61
Entering into a long term relationship is not code for taking the other person or your relationship for granted. Even if you visit the same restaurant once a month, it could be beneficial to ask your mate if another place may work better this time. Keep things fresh when possible and avoid stale situations that drag your relationship down.
Rule #62
Avoid too many obligations and commitments to others. Frequently if one person starts dating another who is close or highly involved with family, the outside member starts blending with family members and may not maintain the specialness they can achieve alone with their partner.
Rule #63
If there are children, they are probably part of the relationship by now. Be careful to consider their needs, but do not ignore the needs of your new relationship. A scheduled date night or two every month is recommended. Planning alone time is essential to keeping some form of intimacy.
Rule #64
Planning Together. Dating someone through all 12 months on the calendar, means there are holidays and vacations to deal with. Please keep all options open to consider your new mate and make positive compromises when possible to make things go as smooth as possible.
Rule #65
Reasonable Expectations. Please keep any expectations you have for this relationship in the reasonable category. Yes, it could last for several years or decades, but don’t expect it to and know that it will take a lot of work to get there as well as both of you experiencing many ups and downs.
Rule #66
Many people in the last century traveled Route 66 to clear their minds or experience one last escape from reality. By six months or longer it is a great idea to plan a weekend getaway or a romantic vacation. Successfully making it through this experience speaks volumes for the longevity of this relationship.
Rule #67
Accommodate. By now, either of you have been spending the night at each other’s place. Be sure these arrangements are still working well and make small adjustments when needed.
Rule #68
Sharing. In transitioning to a long term relationship, it may be okay to share some details with close friends or family. Don’t let them set your expectations for what will make you happy.
Rule#69
How could rule #69 not be about sex! Pushing the envelope. If you don’t know the significance of the number sixty nine, you may want to do some immediate research including the original study written by Masters in Johnson back in the sixties. Be extremely careful about pushing boundaries when it comes to your sex life. Not ever pushing the envelope can lead to boring and stale, while pushing too far can lead to all kinds of problems. Remember there are two components to making many types of decisions, feelings and one’s knowledge of the subject. It is possible that researching more ways to sexual satisfaction together could significantly improve your sex life and give you the knowledge to make good decisions.
Rule #70
Plotting your journey together can help you decide if certain things like marriage, having kids and where you want to live can be a positive exercise. Even though your path is not yet set, the possible paths you can travel together on should be discussed openly with each other.
Long Term Relationship Dating
Long term relationships are usually defined by a minimum of 6 months to a year. By now, a dating couple has passed that initial 3-6 month excitement of dating or falling in love with their partner and is learning more about being with this person day in and day out.
He said: Sometimes I wonder if having a girlfriend who loves me and lets me still be the individual person I am is the greatest way to enjoy being in a relationship. On the other hand, I know that a relationship that is not building and growing, possibly leading to a lifelong commitment, may not last very long or be healthy either.
She said: Having to share my time with one person whom I love is a truly wonderful feeling. Making it into something even better has lots of appeal to me even if it comes with a lot more work. Sometimes I have to admit, that I don’t put enough work into it to make it last.
Rule #71
Communicate. This is where couples who have been communicating for a while go astray. Just because you know this person pretty well, doesn’t mean you can get lazy with your five top forms of communicating. Note: He really doesn’t know what you are thinking. Even the best psychic in the world doesn’t, so please keep the communication lines open and flowing.
Rule #72
Work on making many of the little things better, as well as the important ones. There is nothing like getting a year more into a relationship and letting it fall apart because a little maintenance is involved. You wouldn’t buy a new car and not service it for the first 12+ months, so don’t treat your relationship worse than your car.
Rule #73
Just because the world may know you as a couple, doesn’t mean you have to become sedentary or complacent. The real honeymoon in a relationship is the first year of dating. Keep all the approaches that have been working alive. Be affectionate and attentive to each other.
Rule #74
Make Allowances for time for your partner to have friend, family or co-worker time away from you. Discuss whether guys night or girls night out is a good idea to try. Don’t be jealous of your partner if this is a productive thing for your relationship and growing together.
Rule #75
Don’t miss any important moments in your partner’s life. Even if your schedule is demanding make sure you make it to every important event possible and be happy to support your significant other.
Rule #76
Keep building. You may think you already have a strong foundation in your relationship, but failing to strengthen it may result in a collapse down the road. Go back to healthy habits that help build a stronger relationship.
Rule #77
Find your balance. Sometimes the hardest thing to balance is work, family and a relationship. Ask for help and ideas from your mate. Make your schedule work as well as possible for your relationship. Remember, most everyone has replaced a lost job, but few can find a replacement for a long term life partner or soul mate.
Rule #78
Find new challenges you can conquer together. Too often people get into a stable relationship and then pursue only passions they seek for themselves.
Rule #79
Find new ways to fall in love all over again or be happy with your mate. The trick to finishing a marathon is to always keep yourself motivated and keep running. Long lasting relationships keep both parties motivated in many different and refreshing ways.
Rule #80
Be a team. Always have each other’s back even if you are not in complete agreement on something. There is no “I” in team, but there are two “I’s” that come together in the word winning.
Guide to the Conclusion of Dating
Every single dating experience will end at some time. Death or discontinuing the dating process or relationship will come to every relationship. The goal is when the time comes to end a dating relationship or experience to make that process much more preferable and painless than death.
Rule #81
Never break up via text, email or ghosting someone. This is so immature and juvenile that people who frequently do this should not be dating at all. There may be an extreme case where this could be necessary, but please avoid it all costs. Talking things through with someone who you have cared about can set up a basis for possible friendships or building goodwill.
Rule #82
A one and done dating experience can be handled with a phone call. If you plan on not dating this person again, please discuss it with them as early as possible so they don’t feel like they may have been lead on. There is no good reason someone wants to hear why they have been rejected, so explain why continuing the process right now could not or would not possibly work.
Rule #83
Short term dating can be best ended with a series of phone calls. A face to face meeting can be more effective if you still care for this person, but have to move on for reasons other than you found somebody else.
Rule #84
If you are involved in a long term relationship or dating experience, suddenly cutting the other person off is a good way to make a lot of enemies. Dating is hard enough without adding insult to injury. Be delicate, but firm when dealing with someone you intend to end things with. This process will take more than an hour some day to unwind the two lives wound together over the past several months. Offer ways to stay somewhat involved in each other’s lives for the immediate future if that is something that could work out. Even staying in touch and helping each other transition to the moving on stage can be helpful.
Rule #85
If the two of you made it all the way to marriage or something very similar, then use professional counseling first to see if there is a way to repair the relationship. If all attempts made have failed, then seek legal counsel to separate from each other. Remember, attorneys get paid in billable hours, so resolving any conflicts resulting from the end of a relationship in a timely matter may not be what they are trying to accomplish. You can still work together in resolving separating your lives if you both want to.
Rule #86
Never say let’s be friends when you really mean, “Please get out of my life and never talk to me again.” If a real friendship is desired, then offer a real friendship if the other party is in a forgiving mood. Believe it or not, not all exes hate each other forever.
Rule #87
If you have made great relationships with your mate’s close friends or family members, don’t continue to spend lots of time and effort with them, unless there are children born out of the relationship. You can keep these people listed in your social media while you slowly move away from any kind of consistent dialogue or time spent with them.
Rule #88
If the reasons for ending the dating relationship were mutual and there isn’t any bad blood, feel free to follow up with your new ex as a way to stay involved from a distance. Offering mutual support or comfort is a beneficial way to transition out of your recent time together so both of you can hopefully find someone to try to date or love again someday.
Rule #89
Never return to someone who you have had a relationship with that has abused you, poorly treated nearly everyone, or is abusing drugs or alcohol. There are other vices to include here too, such as sexual or gambling addictions that make starting up with someone again a terrible decision.
Rule #90
“The Golden Rule.” Always treat others the way you would yourself want to be treated. Whether it was the start of a new relationship or the end, keep the “Golden Rule” spirit alive when relating with others. How they react to your positive behaviors is totally their responsibility.
General Rules for Dating
Rule # 91
Do not prejudge! Dating can be a solution to finding out what a person has to offer, what they are about and how they will hopefully treat you.
Rule #92
Set reasonable expectations for your dating experience. Goals like finding the perfect mate or getting married by next year are not realistic and will make dating seem useless when it does not meet those unrealistic goals.
He said: Sometimes I have to keep myself from automatically expecting a lady to be well versed in some of the qualities I am looking for. This makes me make a mistake by not taking the time to appreciate all the things she does have to offer.
She said: If I am dating someone, I am often guilty of deciding what the future will be between us even before the first date starts.
Rule #93
Set limits on the amount of time, money and effort you can afford to spend on dating. Often we let emotions dictate what we can allot versus the reality of how much time or resources we actually have.
Rule #94
Be prepared! Life happens while you are waiting for other things to happen. Look from within to decide if you can date lightly or be ready for your next relationship. Get your life together as well as you can, so your unpreparedness does not interfere with good dating results.
Rule #95
Check your bags at the curb. No one enjoys traveling with someone carrying over 3 suitcases. Work to reduce most of your emotional baggage as well as any others like financial or physical.
Rule #96
If you feel you haven’t been meeting very many good dating prospects, do some research to find the best places they may be. Social groups, recreational teams and people taking classes on topics you like, can help you find possible dating partners with whom you have something in common.
Rule #97
Never give out too much personal information, especially early on. Until you know this person you are dating extremely well, they should not be trusted with your identification. You never know when you are being conned until you already have been.
Rule #98
Be cool, not cold. It is okay to withhold some enthusiasm for your dating partner, but don’t give them the cold shoulder when you really want to be with them. Playing hard to get can sometimes lead to pushing someone away completely.
Rule #99
Use the New Year’s Eve or Birthday rule for kissing. After you have spent some time with your date, you can think to yourself, “If this was midnight on January 1st or my birthday, would kissing this person be wrong?” If it is wrong, settle for the harmless kiss on the cheek or a hug instead.
Rule #100
Try not to bring your multi-tasking skills into your dating life. If you are starting out by casually dating around, keep the population small, like 3 or less so you can adequately evaluate what you like or don’t like about the people you are dating. The “Bachelor” approach to dating more people than you can possibly keep track of will fail just about every time.
Rule #101
Have Fun! Remember, relationships will require some work at times, but dating should always be about having fun, so make having fun the priority!