Beware The Woman Who Upgrades The Date #atwys


Age: 45
State: NY
Question: I will describe the circumstances of my recent first date and then ask a couple of questions. Met a girl online and we exchanged a few emails and phone calls and set up the date. Since I recently moved to her area, I suggested we go to a Houlihans or TGIFridays for drinks since I didnt know any other places. Besides, I was familiar with those establishments atmosphere wise and price wise. She then said she preferred a wine bar she frequently goes to instead. I agreed.

We each had 2 glasses of wine (way more expensive than Houlihans or Fridays) and after 2 hours she said she had to leave. The conversation up to that point I thought went very well and there was even some minor shoulder touching when we spoke. SO at that point I knew I enjoyed it more than her. When the bill came, she didnt offer to pay but did say thanks.

When I walked her to her car, I got the cheek kiss and a hug. At that point it was obvious she wasnt interested and we parted. The next day she sends me an email saying I was sweet but not right for each other.

Now the questions. Since she didnt feel anything, should she have stopped after the first glass of wine and maybe had water or soda instead? If she did order the second glass, should she have at least offered to pay when the bill came? This bugs me because she upped the ante on my original suggestion to a more upscale place from Houlihans to that wine bar. Had the same scenario played out in my original offer, it would have cost far less.

I feel like she was in a win-win situation. She gets a potential connection or else a free night at an upscale place. She says she dates frequently and has been on all the dating sites for years (she told me this in person on the date). Sounds to me like she knew exactly what she was doing. Am I being too sensitive about this? At least I found out about a cool new place for any future second or third dates with another girl.

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She says she dates frequently and has been on all the dating sites for years (she told me this in person on the date). Sounds to me like she knew exactly what she was doing.

No, she doesn’t know what she’s doing. If she did, she wouldn’t reveal something like this, as it makes her look horrible.

The reason why she’s been on these dating sites for years and has so many dates is because she sabotages herself by admitting things like this. No doubt she went back to her friends to retell her tale of the rube who invited her for apps and drinks at a chain restaurant. That is why she went out with you, whether she realizes it or not.  She’s a lousy date who thinks she rocks first dates. I bet she just can’t figure out why oh why she can’t meet a “nice guy.”

And that’s why she’s single.

Now, as for you. The minute you suggested TGIFs, you were sunk. She saw you as the little deer in the field, all naive and wide eyed. Should she have ordered a glass of water or soda when she decided she wasn’t interested? No. She was in a wine bar. You don’t go to a wine bar and order soda or water. You should go into any date expecting to fork over X amount of dollars. (As should the woman, whether her gaggle of singleton girlfriends agree or not.) She was there so she could say she had a date, and she didn’t offer to pay because she needs to be able to say that she “never” pays for first dates. She was going to make the most of it. If you wanted her to pay her share, then you should have asked her to. Would you have come off cheap? Well, listen, you originally suggested Dave & Buster’s or whatever. You couldn’t have done much worse. But even if you did, who cares? The first clue that she was probably going to be difficult was that she took your suggestion and then, as you said, upped the ante. If someone says, “Hey, let’s get a pitcher of beers and wings!” what they’re telling you is how much they expect to/can afford to pay. This is called reading the signals and social cues, people. To suggest that you and your date go some place that will probably cost twice as much not only shows your utter lack of social graces, but makes it abundantly clear to your date that you don’t give a hoot what they want.

This bugs me because she upped the ante on my original suggestion to a more upscale place from Houlihans to that wine bar.

You had two choices. You could have done your research and found another place, or you could have stuck to your original plan and shared breadsticks at The Olive Garden. You’re pissed because you were duped. And I do agree that you were duped. This woman knew exactly what she was walking in to when you suggested Houlihan’s. She took that ball and ran with it. She knew she wasn’t going to see you again. But it was a night out and a possible blog post or “funny” story she can tell the next time she’s out with perpetually single 40+ friends.

You see, we reveal a lot about ourselves and our dating history and experience when we make these seemingly off the cuff and innocent suggestions and statements. The trick is to pick up on these clues so you can devise an appropriate and productive course of action.

What did I learn about you? Well, for starters, I learned you don’t get out much, since you had no sense of where to take her for the date and you apparently didn’t think to use Google or Yelp and find a better spot. Then I learned that you’re kinda cheap. Which, sorry, you are if you thought Red Lobster was an ideal date spot.  The fact that she suggested a more expensive place and the fact that she brayed about how long she’s been dating online and that she’s been on many dates shows she’s lacking in the self-awareness area, entitled and doesn’t actually want a relationship. She’s a lifer. She’ll be on those sites for years to come. Look for her text.

Going forward, you need to get a sense of your surroundings and get up to speed on good date spots. If you pick a spot (and the bar doesn’t have a Whack a Mole machine) and the woman renegs and suggests someplace else, know right then you’re in for some work and expect to spend more than you thought. Stick to your guns. If she bails, good riddance. Ladies, if it’s so important for you to be taken on a “proper” (read: “classy”) first date, then plan and pay for it. I don’t think you gals understand….these guys don’t have to go out with you. They likely have plenty of other options.

Even the average looking dudes.


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28 Responses to “Beware The Woman Who Upgrades The Date #atwys”

  1. Eric Says:

    On Nov 4th 2013 you wrote an article that included advice to check the menu at first date spots to be sure the place isn’t overly pricey but here you criticize the guy for being “cheap” for suggesting a Friday’s? That’s rather inconsistent.

    • ATWYSingle Says:

      Unless you live in a small town where chain restaurants are your only real option, you should choose a more appropriate date spot. Choosing a chain restaurant when you live in NY or even a suburb of NY makes you look cheap and unsophisticated.

      • Lisa Says:

        But are ppl really going on first dates for the ambiance of the restaurant or an impressive dining experience?

        It could be a Starbucks or Panera for all I care. I just want to see what he looks like, exchange a few pleasantries and decide if I want to see him again.

        I think this kind of thinking (must impress the date w/ a sophisticated choice, must not be a “cheap date”) sets ppl up for all this dinner whoring. Just go and meet. There’s plenty of time later on for all the fancy stuff.

        • Donnie K Says:

          Moxie’s point is that there’s something tacky about choosing a chain (especially TGI Friday’s) when there are so many other options. It takes all of five minutes to Yelp a decent neighborhood bar anywhere in the NYC area.

          A beer at either place costs the same but it’s the atmosphere that matters.

          • Lisa Says:

            No, she said/implied that he should have been willing to spend more than TGIF. That choosing such a place made him look cheap.

            • Donnie K Says:

              That’s not how I’m reading it. The minute I saw the OP suggested TGIF or Houlihan’s I knew he was sunk as well.

              I don’t alays agree with Moxie but she nailed this one.

              How hard is it to find a decent neighborhood bar in NY?
              (I answered this in my other posts).

        • C Says:

          I think there are different expecations at play for the first offline meeting. Some folks (myself included) prefer to think of it as a “first meeting” to see if this is someone I want to date. Others prefer to treat it as more of a “blind date” and set the mood for romance. If the LW was trying to romance a woman with a beer from TGIF while sitting next to a gaggle of drunk college students, umh, yeah…no….

          As far as dinner whoring goes, yes the woman should have paid for herself, but I’m not sure I would call 2 glasses of wine and no food an extravagant night out.

          • Donnie K Says:

            First of all, she upgraded. On top of that, it’s common courtesy that if you’re not interested you should leave after one drink. If not, have some class and at least offer to contribute.

  2. coffeestop Says:

    I had the opposite problem recently, I always hear dudes on the internet complaining about how women expect them to pay to so I swooped in and paid for dinner on a date and the man I was with looked like he was going to have a stroke. It was not a chain restaurant but it was inexpensive, I guess I violated the middle aged Bro code. I guess the whole split it up the middle is the way to go.

    • fuzzilla Says:

      If there’s one thing this site has made abundantly clear, it’s that men definitely notice and pay attention to how you act w/r/t finances on the date. They resent it if you don’t offer to contribute, but some men will take your paying as a sign that you’re not interested. Best to take it on a case by case basis and ask how they want to handle it. I grab my purse and offer to split. I did that on the first date with my current fellow and he just asked me to cover the tip.

      • Lisa Says:

        I let them choose whatever type of restaurant they feel comfortable with. If they give me several choices, I pick the one I genuinely want to go to. If they ask me to choose, I pick a cheap chain restaurant that I genuinely like that is convenient for me to get to and hopefully convenient for him too. But no, I don’t pay or offer to pay. For any of it. I will thank them when they grab the check and later when we’re saying good night. That seems sufficient to me and I’ve never heard any complaints or felt any tension over this.

        • Donnie K Says:

          “But no, I don’t pay or offer to pay.”

          A lot of guys resent this – especially the not offering. If you’re interested, problem let the man pay, if not, pay your fair share.

      • C Says:

        Damned if you do. Damned if you dont. Lol. Hard to know if you are on a date with a traditional guy or non-traditional guy.

        I found the same. Best to expect to pay but to follow the guys lead. If you reach for your wallet and says “I got this”, let him get it.

        I honestly dont remember the last time a guy let me pay for a first date. By the 2nd or 3rd, I will usually insist on paying for something (i.e. dinner, desert, the movie, the tip, something…) and add something about being appreciative of them paying for everything else. If any guy was ever put off by this later offer, they didnt let on.

        • Donnie K Says:

          I agree it’s often hard to tell. I think what you’re doing by insisting on contributing to dates, 2,and 3 is the smartest approach. If the woman doesn’t offer at the point I start asking myself, “what’s up with this person?”

  3. Colin Says:

    This is all B.S. as far as I’m concerned. The point of the first meeting (especially if you meet someone online) is to simply get acquainted. With half of the people I met online, there never was a second date anyways. The way I see it, if she is mature, non-superficial, and truly likes you, the location of the first meeting wont matter. NYC is a woman’s paradise as far as dining goes. I’ve met women online that acknowledge being treated to dinner 4-5 times a week. That’s where the term “dinner whore” comes from. Now, if she decides to go out with me a second time, then I’ll treat her to a nice dinner.

  4. toni Says:

    American men are so damn cheap. This entire situation is pathetic. Go pick up women in a bar if you cant afford a decent date. TGIF? What are you? 17? Ugh.

  5. Donnie K Says:

    Moxie’s got a valid point. TGI Fridays is tacky. If you live in Manhattan, Queens, Brooklyn, Hoboken, or Jersey City it doesn’t take much research to find an Irish Pub or someplace a little more date friendly. In some towns, for example Weehawken, there’s next to nothing in terms of bars/restaurants except for a Hoolihan’s and a Charrito’s (which is BYOB) so the chain option is the only option.

    Cost is not the issue- a beer or gloss is going to cost about the same at most bars/restaurants.

    What this woman did was rude and the OP sounds self aware enough to realize he got taken. The good news is he didn’t miss out on much and can chalk this up as a lesson learned.

  6. Yvonne Says:

    I don’t think we can assume that this woman had no interest in John going into the date and was attempting to “dupe” John. I’m going to assume that she did. The fact that she’s been dating online for a long time (plenty of people are in that boat) doesn’t make her suspect in and of itself, but talking about it on her date makes her sound a bit clueless.

    When a man asks me out on a first date, I think it’s polite for him to offer to pay. Many women think that if the man offers, it’s a sign of interest. If I am interested, I will let him pay, but if I am not, I will offer to split the check.

    Personally, I wouldn’t be that interested in meeting someone at a chain restaurant/bar, and if I knew they were new to the area, I’d suggest a local place, but not an expensive one. But how much more expensive could it have been for a couple of glasses of wine? And at least the wine was better than you’d get at TGIF.

    I also don’t like drinking on an empty stomach, and think it’s thoughtful if the man offers to split an appetizer. Maybe the woman thought he was cheap because he didn’t suggest that either? The fact that John is taking the time to complain about all of this does make him sound cheap. It’s not like he bought a pricey dinner as well.

    • Donnie K Says:

      I agree except on the last point. If you want an appetizer, say something and offer to pay for it. Better yet, eat something before the date. If the woman was turned off by John not offering to feed her, maybe that’s another reason why she’s single.

  7. mindstar Says:

    Of course Toni. A man’s only value is the money he can spend on you.

  8. Tinker Says:

    1. I don’t really have anything against Fridays or houlihans but the OP is 45- has it truly never crossed his mind that some may call a first date at these places tacky?
    2. How could 4 glasses of wine be more expensive than food and drinks at houlihans or Friday’s? (Hint: I don’t think it was)
    3. Since she knew she didn’t like him it would’ve been nice and appropriate for her to pay her share. But since people don’t always do the nice and appropriate thing, she didn’t. Unfortunate but it was 2 glasses of wine. Not 2 glasses of wine, apps, dinner and desert. In the grand scheme of things this was not that serious.
    4. She was socially inept for sharing how long she’d been online. But just the fact that she has been on for so long doesn’t automatically make her a bad person right? If so, them bad people abound.
    So to answer the OP’s question yes, he’s being too sensitive.

  9. Damien Says:

    Is this a re-post from an earlier article? I seem to recall reading this before. If only we could do a "where are they now" section to show where OPs and hapless daters end up a year or ten years after "graduation." I really believe that people are who they are and their experiences and life path are the result of that.

    • Kyra Says:

      It is a repost, but there was conversation on it a few days back that got wiped when the new comment system was implemented. Poor Moxie was having major site issues, which seem fixed up now.

  10. Kyra Says:

    If I ask to upgrade a date, which would be so uncouth that I'd probably never do it, then I would definitely be paying for the date.

    But honestly, both the writer and his date just sound incredibly immature.

  11. Tara Says:

    The OP is cheap, and his date shouldn’t have had that second glass of wine if she wasn’t interested in him.

  12. Letty Says:

    You have to understand that not many people have the income to spend their fair share. That’s what most people don’t understand (smh). He’s better off without her.

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