Dating With Dollars: A Woman’s Perspective
  • Posted Feb 20, 2014
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Let’s pretend for a second that we’re all here to find true love. No arrangements, all the strings attached, and definitely no dating for dollars. Dating with dollars? Now that’s something everyone should be doing.

If you think about it, every date includes a price tag. But an actual financial incentive to walk away with is revolutionary. While technology has made dating easier, it hasn’t made it more efficient. There’s so much clutter to cut through in order to get to the good stuff, and money motivates almost everyone.

Aint Nobody Got Time For That

Contrary to popular belief, not every twenty-something female is looking for a hand out. There just isn’t always time to wait for serendipity to make a rare appearance and intervene in your tragic love life. So if you’re sick of the men who are already in your life, there are really only two options: Go out or log on.

Going out is such a gamble, and holding out for fate is such a drag. But if you choose to take your search for love online, there are a plethora of dating sites at your finger tips. So many choices, and that’s only the beginning of the battle. Some of these dating websites make you fill out questionnaires and lengthy profiles before you can even get started. So by the time you get around to seeing who is interested in you, you’re so exhausted that you quit your search for the one before you even really begin.

There’s just no real incentive. No guarantee that things are even going to work out if I fill out this profile, much less go on a date with someone I met online. But what if you dated someone who actually valued your time?

Dating With Dollars

Enter the online dating auction. They say the road to hell is paved with good intentions, but then again, so is heaven. No matter how you date, not everyone you encounter along your journey from singlehood to the altar will be TheOneWorthy. There are going to be a few duds, douches and detours along the way.

This is a fact of life. But wouldn’t it all hurt less if you were compensated for the ones that didn’t work out? And then, what if it does? Sometimes, it takes a little incentive to win someone over. It just takes a foot in the door (or the heart?) before you’re all in. That’s how Spotify got me. And come to think of it, Netflix too. Now I’m a user for life.

It’s an effective marketing tactic, and isn’t dating all about marketing yourself to potential partners?

Risk-Free Dating

Something magical happens on a date. With traditional dating, you would go into a date, immediately wondering where things are going. There’s so much pressure that it takes out all the elements of fun. But when you know going in, that this person isn’t all talk, because they actually put their money where their mouth is, and all because they wanted to get to know you…. now this changes everything.

These men want one chance and are willing to put money on their line for a shot. What’s there to lose?

How has dating with dollars changed your approach to dating?

Would you ever go back to traditional dating?

20 Responses to “Dating With Dollars: A Woman’s Perspective”

  1. David says:


    I have not been on a single date from this site where they young lady has been interested in me, just what they could get from me. The few that I saw several times turned into requests for additional funds or shopping excursions.
    The positive side is that I had enjoyable times in the beginning as it was nice to be dating women who fit the profile of what I desired in a partner. Unfortunately they were interested only in what I could provide for them. This has grown old at this point and I don’t believe I can find my person on this site.

    I must really know how to choose someone as the women I have been on more than one date with have all been deceitful and I am very tired of this. I have to say that the several times I have issues and sent emails to this site they have been answered quickly and professionally. I think this site is a great idea and I know it must work for some, just not me, yet. I will continue to date using this site but at this point if my $50 offer is not accepted, oh well. I have found that no matter what my date has cost the quality of the date has been pretty much equal and the young ladies that are asking for more are earning a good living off of dating on this site.

    • Bobby the K says:

      Great post! I love. If you love it. Then you can love it purely. Just love it. Love it when the girl only likes you for money. Love every minute of it. Love her for it. And then something strange happens. Pure greatness!

  2. The Truth says:

    I do not believe that any women in their 20’s on WYP are looking for love. That’s eHarmony. Women are on here to get easy money. I do believe some actual believe that Brad Pitt or George Clooney types are on here and yes they could fall in love with them.

    I do believe this site is slanted towards women.

    How about a site where the women bid on men, not with money, but with what “they can offer”? I am not talking about x-rated things either.

    • APB says:

      Truth, it is!

      Good luck making that happen, though. Check any other personals site and see the woman’s “about me” turn into “I work hard and player harder. I love going out or staying in. I dress up or wear jeans. I want a man who blahblahblahblahblah but doesn’t blahblahblahblah….”

      All I’d ask in return is a gal who can keep a decent home and make cute kids with me. That’s not exactly a backbreaking livelihood.

      That must be out of style now.

      I should try that on POF. I will ask the women what they can offer me in return for my attention. I have a feeling I would be banned very quickly for being a perv.

    • Cascades says:

      eHarmony is a site specifically oriented towards folks with rather traditional values. Love has many, many forms that are not necessarily traditional. Cole Porter was overwhelmingly gay in his sexual activity-but the love of his life was a woman. Swingers according to the literature have happier, more stable relationships than the general public. My own first stable relationship was with a sugar baby that wanted a ‘boy toy’ for more purely sexual purposes. These relationships are not appropriate for eharmony-but I would’t stay they were loveless.

      A lot of the women here from what I have seen are afraid of being burned–and they have really put a lot into dating guys that were in the final analysis leeches. I am not sure if asking for money up front is a perfect solution–but it is at least a protective measure. I like that WYP has implement Red a background check feature. I would like to see more in that area–for example verification of drug and std status.

  3. Cascades says:

    I have had better experiences on this site. Now, I generally keep my bids low-basically in the range of what I expect a woman could earn at her job–plus her transportion costs. I include her time getting ready as part of it.

    I have met women that really want to date-but cannot afford to date without some help. One was a seriously struggling single mom who really wanted some adult conversation–and my tip was diapers for her kid. She actually felt guilty about accepting my help–and rather than date guys like me that
    would have valued her time/consideration, she took a dead end job
    that fit in her idea of what was respectable.

    Another was a rather attractive, athletic woman who had been stood up on
    several other dates. I was not her cup of tea-but it was still a fun date.

    I made one genuine friend–who has helped greatly with some urgent issues I needed help with–getting resources for a relative that needs care.

    I have had women that backed out of dates or that were less than graceful–but honestly they were not hard core money grabbers. Frankly they had no idea what making money was really about-and might be better off if they did.

    I think the 20 some things are more in it for novelty than the money. I do not see them as really seriously trying to maximize revenue the way a serious sugar baby does. Yes i have known such women–and there are only a few here. Some may aspire to that status–but they are really more focused on finding the guy that is too good to be true–not the guy that really can reliably deliver on realistic terms. However this site may educate them in that respect.

  4. Cascades says:

    One feature that I would like, is the ability to give a gift that amounted to a conditional, charitable donation. If the lady goes through with the date, the donation goes to a charity of her choice, it she does not,it goes to a charity of the choice of the guy or can be applied to a later date.

    I think some women are uptight about taking money from a guy–but they get excited that a guy wants to date them enough he will do something financial. Usually this involves spending money on restaurants bars and such-but i have seen some serious quality women date guys that were volunteering to a cause they believe in.

    yes, the woman could just take the cash and donate it –but if wyp holds the cash, it means the guy can get the tax deduction–and the woman has a sure thing if she shows up.

  5. The Truth says:

    Cascades, the majority of the women I see in my area are sugar baby types-doing the least to get the most money.

  6. David says:

    Said this before but:
    At least 3 dates were smokers although they stated they were not. Deal breaker for me.
    One was married, listed as single. Wanted me to keep paying her for dates when I offered to just hang out as friends.
    1 brought her sister along. They ordered enough food for at least the week asking for many take out bags. We went for a walk around the mall and they asked me to buy them both clothes. She also asked for me to buy her and her sister new cell phones.
    1 showed up with a friend after telling me it was her birthday and asking me to take her shopping with her friend after dinner.
    1 was a drug addict.
    3 never showed up.
    2 asked to go out again then asked me to pay her again.
    3 looked nothing like their photos.
    5 accepted offers but never bothered to reply to emails or texts sent to them.
    A few were nice normal dates, but we just did not hit it off romantically. This is fine but the awful ones where much more prevelant.

    I am kind of fed up with the women on this site.

    • The Truth says:

      Yeah that is about the norm on here….

      • Cascades says:

        I think you need to compare the norms on wyp to the norms on other alternatives that are available to less obviously traditional folks.

        A white guy with a reasonable job can go to mormon singles ward–and will have pretty decent marital options. Those come with the expectation of 10% of all your income the rest of your life–substantial volunteer expectations, constraints on your social life and expectation you raise your kids in a rather traditional structure–but granted there are also substantial benefits in areas like employment.

        Eharmony has fewer costs, but less obvious results and fewer side benefits.

        It is fairly hard to get ANY date on sites like craigslist/pof/okcupid for many of us. The sad fact is that men outside the upper echelon of guys with extremely good looks, lots of money, fame/political status often get treated pretty badly in a dating context.

        I wouldn’t necessarily expect direct results from wyp. However, I would expect horrible results from letting yourself go 2-4 months without a date. WYP can let you get date with someone you might never get a date with otherwise. It can also help fill in gaps.

      • Josh says:

        Cascades, do you work for WYP?

        Either you are a spokesperson for WYP or living in some virtual world we are not living in. Also, you just must be too desperate to pay these fraudsters to date you.

  7. Bobby the K says:

    The way I look at this site is “reality”. Unless you’re Charlie Chaplin, rich, famous, charming, and extremely funny, (he actually married an 18 year old beauty at age 54(?)), I say go in with extremely low expectations and have fun, be well-mannered and respectful. Life is what it is, so take it all with a grain of salt. That’s the only way to get your money’s worth on this site and to have fun at the same time.

    • Cascades says:

      i think you got the picture here. wyp is not for everyone–but if you have more disposable cash than looks/charm, it is a way to get started. I have never had much problem turning a date into a relationship. I have made relationships in situations which many men would regard rather difficult. I have had real issues getting that first date-and some real consideration.

  8. Alex says:

    …just a couple of ideas to add. If WYP required each “Attractive” to be verified (provide some form of validated security card, Trusted Faces, etc), it would be a huge plus for the men paying the fees.

    Granted it would probably cut the number of women down by (guessing) 75% but the 25% remaining would be much more desirable and yield greater positive results.

    It is clear when looking at profiles today compared to 6 months ago, there are many more “completely self-focused” women on the site. There are sites for those and many ate registered there. In order for WYP to maintain it’s market leading position and at a top-dollar , it needs to tighten up and drive away bad business.

    • The Truth says:

      I think it’s a good idea that women should be clear with what they want. It’s also very disheartening to hear things like “I am a princes”, “I deserve to be spoiled”, “I have taken care of others in the past, now I need to be taken care of”. It’s time to talk normal and realistic.

  9. jaybo says:

    I like some of the others here didn’t have a great experience on the site. All being fair in this process and like other sites- we who pay a lot for this opportunity should have the option to rate the dates. this way we would have some idea what the situation is before the date. No whining here, I understand what this site is for and they do too, so make it fair like in any transaction. I want to know what I’m paying for or at least know when I may get screwed or not – and not in a good way.

  10. Felix says:

    Sounds like Cascade is very lucky or lives in an area that is different. OR HE WORKS FOR WYP like others have mentioned…

    I agree with all the other posters over what Cascade has mentioned. Most see this as a part-time job more than actually wanting to get to know someone. This is not all the women…but a good amount that makes the results less than desirable.

    If I had to gauge my results, I would say out of 5-6 dates, 2 of them were actually looking for a connection. MOST DON’T UNDERSTAND THE DYNAMICS of this site and demand the date amount on subsequent dates. Utterly ridiculous.

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