Messaging Etiquette – Do’s and Don’ts
  • Posted Oct 12, 2012
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Sure, online dating enables you to interact at the click of a mouse. But that doesn’t necessarily mean dinner and drinks is a sure thing. He or she may like your initial offer, but first impressions only last so long. Make an even bigger impression by following these messaging guidelines…

Are you as charming on the computer as you are in person?

  • DO be honest and up front about your expectations.
  • DO use proper grammar. Messaging “Woow u r hawt!” is not attractive. Knowing the difference between “your” and “you’re” is.
  • DO write in letter format, not texting format. It shows effort.
  • DO reply politely, even if you’re not interested.
  • DO introduce yourself before asking for their real name.
  • DO integrate their profile information into your message. It shows genuine interest.
  • DO ask engaging questions.
  • DO share personal information after you have built a rapport with your date.
  • DO limit the use of emoticons. You’re not in middle school anymore.
  • DO treat them with respect, even if they don’t agree with your terms.
  • DON’T just wink without messaging.
  • DON’T explicitly ask for sex. Paying for their time doesn’t make them an escort.
  • DON’T send the same message to multiple people. They can tell.
  • DON’T start your message with a pick-up line.
  • DON’T message or reply with one or two words (i.e. Hi There, Hey Sexy, Wanna talk?).
  • DON’T immediately ask for “pics” or their phone number. Once a mutual trust is established, these topics are fair game.
  • DON’T be pretentious or rude, even if you are the benefactor.
  • DON’T curse or swear.
  • DON’T use nicknames/pet names without knowing the person.
  • DON’T send multiple messages in succession. It comes off as desperate and sometimes creepy.

What are some other common do’s and don’ts when messaging other members?

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40 Responses to “Messaging Etiquette – Do’s and Don’ts”

  1. Leroy says:

    All personalities and perspectives are welcome in this blog, while personal attacks and name calling are not. It’s inevitable that there will be disagreements, but let’s handle it as mature adults with class to keep the dialog constructive and respectful. Please refer to “Blog Etiquette” on WhatsYourPrice blog for more details.

  2. Magno says:

    Don’t just wink without messaging? This makes absolutely no sense because a generous or attractive member cannot send or receive a message until an offer is made and accepted by the other party. This is why a generous member might have a mountain of winks piling up, with no communication whatsoever taking place.

  3. Plzbelieveme says:

    WYP makes us pay 10$ to just message someone, i send a wink to see what the girl offers then I can either counter or accept if its reasonable

  4. Guys. A big turn off is when you ask if the girl is willing to have sex on a first date. That makes her think that you’re only interested in one thing. A classy lady likes to get to know a man before even thinking about sex.

  5. chris says:

    I like to offer 500 so that i get treated vip style. If shes not the girl in pictures or changed a huge amount like much heavier, then i just give 250 upfront and let them know i wanted to meet tge girl in pics for 500 instead.

  6. Magno says:

    I think $150 is a reasonable offer for what essentially could end up being a 20 minute meet and greet over tea and conversation. An offer over $300 puts too much emphasis on the initial meeting, and hence, feelings of pressure on both parties. It’s best to keep things simple in the beginning, until you can ascertain whether or mot a mutual attraction and inclination to engage further is present.

    I personally don’t respond to winks, so the advice above in this column is not relevent to me.

  7. chris says:

    Mango, you act as if you are the teacher to how this site is done. Calm down bro!

  8. chris says:

    My dates last 3~4 hours because i am charming.

  9. Patricia says:

    How long should a date normally last?

  10. Magno says:


    I am about as calm and laid back a guy can be on this fine evening. I am not supposing to thrust my ideals upon anyone, just merely expressing my own personal viewpoint/preference on the matter, is all.

    When it comes to internet dates, I never like to commit to any major complex time intensive plans, just in case I am just not feeling it with the woman sitting across the tanle from me.

    If there is no initial attraction, or feeling of being connected in some way, then the last thing I want to do os feel obligated to spend time with a stranger I just met. Going through the motions for anyone is just plain disingenuous.

    All I am saying is, with a significantly high offer, both parties are more apt to feel obligated to spend extra, non necessary time with someone. It’s human nature.

    If I put an offer on the table for a large amount, then want to bail on the date after 15 minutes, then the woman might feel as if she is taking the money and running. I don’t think that is fair to do to a Lady.

    Conversely, if the amount is modest, and the date is going well, there is always the option of handing the woman more than the agreed upon amount.

    $150 for a 20 minute tea date seems reasonable. If the date continues well into the 2 to 3 hour range, then the assumption is both parties are enjoying themselves.

    But from my personal prrspective, why place that much emphasis, stock, and pressure on a first meeting when it could take a few dates to ascertain whether or not both parties are compatible in a multitude of ways and varying levels.

    That’s just my take. Not trying to ‘act as a teacher’.

  11. Patricia says:

    How would I leave in case of a bad date?

  12. Magno says:


    That is a great question. One that is certain to elicit a wide range of response.

    In my opinion, communicating each other’s first date/meeting expectations during the inbox message phase, before the set upon date and time, is essential in thwarting any potential misunderstandings, or varying expectations in this regard.

    I am sure some attractive members are interested in ‘creative’ first dates, while other’s may prefer to go the route of the 30 minute drinks and conversation scenario.

    I think a lot has to do with exactly how much an attractive male/female feels his/her time is worth, mrasured carefully against the backdrop for the potential of a date that could quickly go awry.

    I personally do not like to commit to more than an hour with a stranger from the internet.

  13. Magno says:


    You would simply thank the Gentleman for his time and attention, and tell him it is time for you to go.

  14. T says:

    I agree with everything except the part about emoticons. I would never use them for work or formal communications. However, they weren’t made for children. They were made to compensate for the inability to convey tone when typing something to somebody. If just one is used to disambiguate, I don’t see how that’s being childish. Somebody could misinterpret your meaning if you don’t use them.

  15. Alex says:

    $150 for a 20 minute date is not reasonable in my opinion. Even if I offer to just meet for drinks, I expect the woman to at least humor me for an hour or so, or else she’s honestly not even giving me a chance. Of course, I know that I’m not a jackass either, while some other generous members may make it clear they are in a lot less than 20 minutes on a date, so I can understand why some dates may last such a short time, but I think it’s unreasonable for the women on here to think that’s acceptable if you’re being treated appropriately by the generous member (i.e., he’s being a gentleman, even if you don’t like him for other reasons).

  16. Pat says:

    I agree with the above. I try to shy away from dinner on a first date especially at anything expensive. I offer to do something fun like going to a baseball game or something similar. I still pay for everything but this way we can both interact and have a fun time. While not feeling like i am being someones free dinner.

  17. betty says:

    This is not the site to be cheap. I always turn down sporting event dates because last time i went i was bored stiff! It was not a sexy date that would get me in the mood for romance. Its like offering to go to a nail salon for a date. Hey, do what she wants for once!

  18. Magno says:

    I am not thinking romance upon a first meeting with a stranger from the internet.

  19. Pat says:

    my point exactly magno. If i agree to a date than i will expect it to be fun and not break the bank. If she wants to see me again than i will do the whole dinner thing. Now i do not have a problem taking a lady out and having a great evening but i will not take her on a shopping spree. To me that just makes her think that i am easy and can be walked over. I did not come on this site to be a sugar daddy. There are other sites for that. It also seems like betty has expensive taste and expects guys to take her to five star restaurants. good luck with that…

  20. Sophie says:

    I feel the conversation is not taking into account that some people are here to date in a normal way and some for a mutually beneficial arrangement.

    Maybe those who will pay a lot for a date are more sugardaddy/generous types and those who want to spend less are more an average guy.

    There are options for all types of dating on here.

    Sometimes the advice seems more suited to the sister sites (SA and MT). We are not allowed to message a man until an offer has been made. So favooriting and winks become the only option to get a generous members attention.

  21. Magno says:


    You make a very valid point. I am NOT on the sister site for the reason you stated. My profile is set for the intention of ‘friendship/activity partner’….

    But that does not preclude me from being generous to a special Lady friend that has invested in me, and earned my trust over time.

    What I don’t understand is a number of women on this site that seem to have entitlement issues. A shopping excursion for a first date? Really? Seriously?

    But the suggestion of engaging in a fun activity like taking in a sporting event, or shooting some pool indicates an undesirable ‘cheap’ man?….when he hands you cash, and pays for all of the expenses incurred on the date?

    I estimate I donate approximately 30 percent of my yearly gross income to local charities, primarily those assisting children, and women at risk.

    So a man that is hesitant to toss $500 to a stranger from the internet constitutes a cheap man?

    Answer me this: was, exactly, entitles an anonymous woman from the internet entitled to a portion of the 30 percent of monetary compensation allocated to charitable organizations that go for an honorable cause?

    If I see another woman on here bemoaning the lack of generous men on this site, I am going to have the urge to up my charitable contributions!

    As for allocating some of those funds to the ladies?

    Invest a little bit of yourself in me, and show me why you are deserving of my time, attention, and affections.

    Again, I am generous to those I hold dear to me.

    One other thing….favoriting and winking aren’t the only ways on here to get a generous man’s attention.

    I won’t even respond to winks.

    A woman can tender an offer to the man at any time.

    I don’t understand why more ladies don’t choose to go this route.

  22. Sophie says:

    I think maybe they fear rejection. I can’t speak for all others of course.

    I have acceoted dates of varyinf offers, but they have never happened.

    I am not one who feels I am entitled to offers that are obscene. So, I cannot answer for those ladies either.

    I don’t like sport. So a first date at a sporting event would not seem cheap to me. Just undesirable.

    I also would never expect a man to give me any of the money he would usually give to charity.

    I think we simply have to accept everyone is different, come on here with differing wants and desires. Some will find matches and others wont. Just like any type of dating site.

    As long as both are honest about what they desire from the match, no one is hurt.

  23. Sophie says:

    wow, that was full of typos lol. I need to stop typing in the dark hehe

  24. SuckerWithMoney says:

    I think that Magno hit the nail on the head when he mentioned “entitlement issues.” Maybe that is because the “asset” of being a beautiful woman—or even “only” a very pretty woman—is a “highly in demand” asset.

    There are far fewer woman in our society that are considered to be “very pretty”, “beautiful”, or “hot” than there are men who fit into the “very handsome”, good-looking” or “hot” categories…thereby making those types of women the objects of desire of many more men.

    That, in turn, gives them the feeling of entitlement that Magno refers to.

    I used the handle “SuckerWithMoney” as a joke…and yet I still get Winks and Favorites from women throughout the U.S.A. Don’t they get the joke…or do they really think that I am going to fly across the country AND pay them money—just to have a date with them?

    And some of the initial offers I receive are ridiculous. Two hundred and fifty to five hundred dollars…plus the cost of my airfare and hotel. Really?

    For that much money, I can fly to Costa Rica…and have GREAT sex with at least 5 different women—all of whom look better than the ones who are making their “offers” to me.

    Wake up women…we are not ALL desperate or stupid…although I suppose there are enough desperate and/or stupid men on this site so that you can make a pretty good “side job” out of going on several dates per month with guys you have no intention of ever seeing again.

    Oh—to be young, hot, and have great legs…even if you are without a shred of decency!

  25. Sophie says:

    SuckerWithMoney: The name of the site may not help entitlement issues.

    Plus there are men with more money than they can spend in a life time. I have met a couple myself. These guys will spend money on what they want, not what they can get for the same amount.

    Because women are aware these men exist, they may be placing high value on themselves. That may be wrong. But it is the nature of how things are these days.

    Once again, we just have to accept everyone is different.

  26. Austinpet says:

    The reason I have never made an offer is that I don’t feel comfortable putting a price on a date… I would never ask anyone who is more than 50 miles away,

    any advice on how to get over this ?

  27. chris says:

    Always keep in mind that hot chicks do not have a need to cyber date. They might if the price is right!

  28. Magno says:


    Have you browsed That site is loaded with really attractive women, so I am not sure I see where you are going with this.

    We are in the age where both genders are exploring online options as a way to connect.

  29. Magno says:


    The best way to overcome your hesitation to tender an offer to someone who is more than 50 miles away is to tender an offer to someone that is within 49.9 miles of your location.

  30. chris says:

    I know the owner of match so i know the hot lady profiles are just profiles to get you to join up. You have to know that also or you would not even be here mango.

  31. Magno says:


    Sometimes, I get the feeling this site also has its fair share of dummy profiles. I have had to block some profiles that were sending continuous winks in rapid succession after I kept rejecting them.

    I figure those profiles on here must be system automated bots.

  32. Sophie says:

    Most dating sites have fake profiles on them.

    I think attractive women can get dates anywhere too. So, I guess the price does have to be right for them.

  33. Gabriella says:

    I think having men to pay to read the message, is crazy. I just put what I have to say to the guy on the “title” of the message; phone number maybe etc… I find that a lot of these websites are all alike for instance, Wealthy Men, Seeking Arrangement etc ( by the way those websites suck) its not fair to men and women

    I’m a woman but in all honesty what’s the point of having men pay to read the message? I look at it this way,

    Man pays for ” Premium” account
    Man pays for ” Background check” so chicks won’t think he’s the next Ted Bundy
    Man pays to read the message
    Man pays for ticket + place to stay
    Man pays for date( meal and drinks) + what he offered her

    And guess what happens at the end of the night????

    He doesn’t get laid, what a shame. These websites are a waist

  34. lovelylori says:

    To those of you who think that extremely attractive women do not go on websites for dates; that is not true. I am extremely attratctive and I have joined many different websites to find a good man because I’m rather shy. Not ALL attractive people are shallow. I know I’m not. Whenever I’ve gone on a date from a website, the guy always thinks that I might look like my picture but when they actually meet me they are in awe that a really nice attractive girl chose them. I’m so nice that they in turn start to treat me with disrespect and then I must cut my loses and start looking for someone new.

    Sophi: I believe you have it correct when you say that everyone is different and one can’t form preconceived opinions for that same reason.

  35. betty says:

    Because you are nice and attractive you get treated bad? That just seems odd. Care to share your profile name so we can be super nosey?

  36. Magno says:

    Do an advance search for the user name lovelylori, and her profile pulls right up. Last logged in date: 08/01/11.

    Her face is obscured in her photos, so quantifying her level of physical attractiveness proves futile.

  37. Austinpet says:

    I meant I would’nt date a man more than 50 miles away… My question was more about being hesitant to make an offer at all.

  38. Sammy says:

    Wow!! I am still fairly new to this site. I had no idea some woman were asking for $500+ for the first date. My first offer was ridiculous!! The guy offered me $11!!! So I countered with $75 and was rejected :-/ I have a very hard time asking for anything, especially money. I have gotten a few offer since that are a lot better then my first $11 one and when I get those offer request where I’m being asked how much I will take I say $175. I figure that is a good number to start the negotiations. I haven’t gotten 1 acceptance from me asking for $175 or $150. I have also accepted a few offers, 4 to be exact but I can’t get the guys to set the date. I’m sure there has to be real people on here from my area. Right?? I hope anyways ;-)

    FYI— I LOVE using and receiving emoticons when emailing ;-)

  39. Nevaeh says:

    Where is the wink option, I dont have it

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