"Maybe it was a dream, you know, a very weird, bizarre, vivid, erotic, wet,
detailed dream. Maybe we have malaria."


The Match.com Files: I need $50 to make you holler I get paid to do the wild thing

By: Bobby Finstock on 11/25/08 @ 12:43 am

After my first round of dates I decided to take some time off, reflect, and consider important questions like what is the exact ingredient difference between Mayonnaise and Miracle Whip? After giving up I decided to get back on the dating wagon. I scheduled date number 4, went on a second date with date number 3, and had a conversation that is leading to a much more complex question than the Miracle Whip/Mayonnaise debate…. We will get to that in a bit.

One of the people that I have been exchanging e-mails with decided that they wanted to instant message me because of the frequency of our e-mail exchange. Because I am constantly in front of my computer for work lately I figured it was a good way to pass the time instead of actually getting work done so I obliged. We talked on and off for a couple of days. The conversation was entertaining and I felt that we had some chemistry going. (Well as much bullshit chemistry that you can have over the internet.)

During one of our conversations the girl, who we will call Vivian, expressed that she has been forced to match.com because it is really hard for her to find or keep a boyfriend due to her job. The subject of what she did for work really never came up so I automatically threw out the typical reasons why jobs create difficulty in a relationship like long hours, travel, different schedules, and things along those lines.

She said no to all of these and then there was a couple of minutes with no reply. I was then asked if she told me something about her that I had to keep an open mind and promise that it wouldn’t impact us going out to dinner? Honestly that is the dumbest question to ever ask anyone. You can’t dangle a carrot out there and think someone isn’t going to say anything to hear it. So of course I agreed. She then revealed to me that she was an escort.

Now I can see why that would cause some problems in a relationship.

Boyfriend: My boss was being such a dick at work today. I am so glad to be home. How was your day honey?

Girlfriend: Speaking of dick dear… Well the first client said he wanted to blow a load on my tits and missed and just plastered my face. The second guy had a weird diaper fetish. And well the third guy… he was just really hung… I almost choked to death. Now come here and give me a kiss.

Of course the conversation totally changed to focus on her business and the 19,000 questions I had about it. She still wants to go out on a date, which I am up in the air about. But if I do go it will be a one date only type of thing, no hooking up and no relationship. I thought about this long and hard:

-probably really awesome in bed
-I am getting $300 of sex for free every time we sleep together so there is real value there

-tasting other penises by proxy
-the increased possibility my penis will fall off

Personally I like my penis attached to my body.

The question is do I still go on at least a date?

About the author

Bobby Finstock

Finstock is founder of Pointlessbanter.net. He is known for his encyclopedia like knowledge on the life and times of Scott Baio. In the future he hopes to write again under his own name in order to impress the ladies and build his celebrity to the levels of other failed internet writers.

52 Responses to “The Match.com Files: I need $50 to make you holler I get paid to do the wild thing”

  1. Chris says:

    I’ll give you the same advice my dad gave me when I started to get my penis wet.

    “Don’t be a fool…wrap your tool.”

  2. Meghan says:

    Only you…

    $300 free sex doesn’t mean great sex. Just means someone else was willing to pay cash for it. Not the same thing.

  3. Isha says:

    Boy, you really attract ‘em, huh?

  4. Charlotte says:

    Bobby Pimpstock has a nice ring to it.

  5. James says:

    Listen Finstock, this is the big game. She likes you, makes great money, loves the cock, time to step up.

  6. Serenity says:

    Does anyone else find it strange that an “escort” is trying to find dates on Match.com? or is it just me?

    • Christine says:

      I agree. What if she is this unattractive bored housewife just messing with your spare time? Don’t know if I’d brave those waters to see but it’s you so let us know how it goes.

    • Yeah my bullshit meter is going off on it… But when I was grilling her with the questions about her industry there was little hesitation and a lot of knowledge… Maybe it is someone that watches a lot of 20/20 specials about hookers.

      • Christine says:

        20/20 or really raunchy novels while the kids are napping and then you have to worry about whether or not she’ll have “company” with her if you go to meet. Eerie. No good vibes on that one. Keep it to chatting Kev. Play this one safe.

  7. Chachi says:

    You gonna bring this one to the Christmas party? It might make for more fun than the usual game of poker.

  8. cigar smoking, beer drinking lawyer says:

    I’m late to the table on this, but hell go on the date. It is just that a date. Go have fun and maybe hear some wild stories. hell interview her for this blog thingie you write – you know the old five questions with..

  9. RizzoTees says:

    I had the jimmy on EXTRA TIGHT!

  10. Joan of Arf says:

    You totally have to go. Hell, how can you not? One date. Think of the research possibilities… the stories that will scar your brain. I’m betting money she doesn’t look like Julia Roberts, but that date will be way more interesting than candlepin bowling.

    Based on Craig’s List casual encounters, some guys totally dig when other dudes fuck their girlfriend/wife. Never know, it might become your “thing”… and escorts need love too.

    • I don’t think I have a problem screwing another guy’s gf/wife…

      No I have seen her pictures on match. She doesn’t look like Julia Roberts but she is on the higher end of the above average scale.

  11. Em Em says:

    I thought you linked an article about this recently… maybe it was somebody else, about how dating sites (though it is mostly Craig’s list…) are cracking down on hookers and now they have to pretend to look for “dates” instead of flat out telling you they’re a prostitute. Then *SUPRPISE* you’re propositioned to pay for sex- which is probably a little annoying once you’ve already paid for dinner and drinks. I mean, that’s usually enough to get an average whore to sleep with you, now you have to throw out an extra $30? I think it might be a rip off Mr. Finstock. =)

  12. Don’t take this the wrong way, but, you might want to try your dating luck at a library or book store or something. I fear for your penis the way things are going. Pus filled shankers and boils with a side of penicillin are on their way.

    Actually, keep it up. I’m easily amused.

  13. Vince says:

    I say go on the date and make her pay that way if you get some action you will know she is putting in some effort because she paid for it.

  14. clientsideshow bob says:

    What will you do when after your evening of 100% consensual, adult pleasure (albeit with enough latex to open your own glove factory) she rolls over and asks for her cash?

  15. Caroline says:

    Go on the date . . . why not. . . ?

  16. Lori says:

    Clearly you gave up on a second date with date number 2. This certainly won’t get you one if you had any chance left.

  17. 8675309 says:

    How much more RED does the flag have to be. As we say in Brooklyn-Italian slang. . . FA SCHKEVE! Then again, you could just as well meet someone on match.com or wherever for that matter who’s just a filthy whore and DOESN’T get paid for it. Regardless, don’t become client #10.

  18. Patrick D. says:

    Dude, that reminds me of a Jeffrey Ross joke: “So, I’m dating this porn star and she’s coming into town. I ask when I could see her. She said she was working Tuesday and Wednesday. How about Thursday? Thursday? How about MONDAY?” It’s funnier when he tells it…but you get the idea.

  19. Branwyn says:

    A hooker/whore and an escort are different things. Unless she told you she’s a “man-handler” then she gets paid to go places. Not do people. There is the chance that she’s trying to be politically correct, lol, and break the news to you easy….but hell, go on the date. You’ll at least get some background for the entertainment that you write here. She’s still a person. And then you will also know you did your good deed for the year. =)

  20. kate says:

    Fucking hoe. Go on the date just because it will almost certainly give you some material.

  21. Carolyn says:

    From what I’ve heard/read/been told by friends escorts are actually a lot safer about sex than most, uh, ‘regular’ people.
    But I cringed at “tasting another cock by proxy”.

    Oh, and man, if it’s between blog material and dating sane people… you know you love your readers more than your own sanity and love life success.

  22. PsYcHo BiTcH says:




  23. Wynn says:

    I would say hellz the no to a date. You’re doing it because you’re intrigued by her as a escort and not as a person? And risk the possibility of her being really into you when you know from the start that it’s gonna be a problem.

    And the $300 is a bargain. It’s like when I get a pair of jeans on sale, they’re 30 dollars now and the original price is 50, I SAVE 20 dollars!

  24. 420 says:

    YOU HAVE TO GO….Y NOT…..U have nothing to lose here…..Maybe something to gain(as a date) and if not then def an exciting date to add to yr resume…..fuck yeah bro…..i say go for it…I have escorts and strippers who I met in my classes and they are pretty and cool and disease free….sometimes I am so happy I got to be friends with them…..B optimistic…….just watch yr back and take it slow….observe…..make sure there’s no dudes following u and thats always a good thing…..Do this quick so you can tell us what happened….I cant wait……lol……do u hav a pic for her?

    • Jeff says:

      “U have nothing to lose here”

      Yeah, except the ability to put “disease-free” in your Match.com profile.

  25. 420 says:

    I said go on the date not stick yr dick in her main hole as soon as u see her……if it does come to that than there’s a saying I go by……POKE THE WRONG BITCH RAW AND GET YR STICK BOUND UP IN GAUZE!!!!double wrap dat shit………

© 2008 Pointless Banter - All Rights Reserved || Designed: E.Webscapes || Social Media Consulting: Comedy Central Sound