Big Life

3 Rules for Men to Follow to Avoid Getting Trapped by Women Who Date for Dinner

3 Rules for Men to Follow to Avoid Getting Trapped by Women Who Date for Dinner

An edited version published originally on the Thought Catalog 5/4/17


Dating, as a middle-aged guy in Manhattan, has been an adventure. What I have discovered is that while I was going on first dates in the hopes of having a second date and maybe even finding a relationship, some women were dating for sport – the sport of getting a nice dinner paid for. All they had to do was manipulate the date logistics in a way that suckered me into buying them dinner and they have achieved their goal. You know the saying, nice guys finish last or in this case, $100 dollars plus or minus poorer, with little to show for it.

Now before all of you ladies start sending me (more) hate mail, I am not saying that all or even most women do this. But some do, and most men who have significant dating experience have encountered this situation. Some women even admit they do it like Rose Clifford, who was featured in a recent NY Post Article. And for those of you who think otherwise, it seems that most women still expect the man to pay for the first date. And essentially every man and woman I have spoken to about this, agrees with that.

Here are three recent dates I had that illustrate how easy it is to get caught in the pay-for-dinner play:

Date #1: When I spoke with her on the phone I wasn’t sure we were compatible but I figured how could a quick meet on a late Wednesday afternoon hurt? I suggested that we meet at a nice bar I knew near her. She said, “I really like the W Hotel. I really like the lounge in there.”

We meet at “The Living Room” in the W Hotel at 5pm and sat down on one of the couches and ordered drinks. About 10 minutes in, she said she hadn’t eaten much for lunch asked to see the menu. And then proceeded to order two “small” appetizers to go with her second drink. The date ended an hour later when she said she had to get home because her babysitter had to leave. There was no offer on her part to even split the bill. I paid the $80 bill and never saw her again. I felt like a schmuck.

Date #2: About a month later and a bit wiser (so I thought) I made plans with a woman who lived across the Hudson River in Jersey City to meet me at by the 9/11 Memorial at 4:30pm. She had told me on our initial phone call that she had never seen it and since I knew several nice places to hang out within a block, I suggested a quick tour of the memorial and we could grab a drink.

At 4:20pm, as I was walking to meet her, she sent me a text saying she was sorry but was delayed and was right now walking out her door. There were two more texts that followed with excuses for more delays. She showed up at 6pm, 90 minutes after our scheduled meeting time.

She was very apologetic, gave me a big hug and said it was unusual for her to be so late and she would make it up to me. I believed her. We toured the 9/11 Memorial for about 15 minutes and then I pointed to a bar within eyesight and said let’s go have a drink. She informed me that at this point she was hungry and would get sick if she drank on an empty stomach and needed dinner first. Three hours later we ended the dinner date with me $125 poorer. There was no offer on her part to even split the bill. There was no second date, despite her reaching out to me again.

Date #3:  I recently matched with a very attractive woman on a picture-based dating app. We had a nice first call and I suggested we meet Saturday, 3pm for coffee. She said had errands to run and asked if we could push back the time to 4pm. I agreed, but that got me thinking. So, I went back and looked at her dating profile and this is what it said:

“Single, no kids, fun, sweet, upscale, business-savvy, selective… Enjoys fine dining in Manhattan and…. That last phrase poked me right in the eye. But maybe I was being paranoid?

Saturday came and I was just about to head to our date when I got the text I somehow knew I was going to get: “Sorry, I’m running a little behind, can we meet at 5:30pm?” I waited a few minutes to think about things, even considering that I might be judging her unfairly, and even if she wasn’t trying to sucker me into a free meal, moving a first date and hour and half later, 45 minutes before the date, is just unacceptable. So, I told her I had plans and her coming at 5:30pm would make our time together too short. I felt like I had finally manned-up.

These three date experiences along with a bunch of others has lead me to suggest these three rules for men trying to avoid getting suckered into paying for a meal they never intended to:

  1. You Pick the Place: If you are paying, you pick the venue for the date. You should know in advance what you are potentially paying for. If she insists on changing the place make sure you know it well and it’s acceptable to you. If it’s not, hold firm and if she doesn’t agree, pass on her.
  2. Late for a First Date is Unacceptable: I’d say follow the 30-minute rule. If she can’t get there within 30 minutes of the scheduled time cancel the date. And don’t get fooled by late creep – where she says I’m running late multiple times before the same date. Even if she’s not being late to get a free meal, she’s disrespected you and that’s not a way to start any relationship you want to be in.
  3. Look for Warning Signs: Listen carefully to what she says or what she has written in her dating profile. If she says she likes fine dining, great wine or frequent travel, you should believe her. She very well may intend on getting you to indulge her in those things. My dating profile talks about what I have to offer women. Her profile shouldn’t talk about what she wants, it should also talk about what she has to offer.

Have you had a similar experience on dates? If yes, did you end up paying for dinner or not?

Good luck men.

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6 replies »

  1. I commend you, Matt, on this one. As a middle aged woman, who’s joined a dating site, (3 yrs ago), and JUST got serious about it 1/1/17, (make that March), I have been so hesitant to even reply to the many messages I’ve gotten. I search the profiles. I look for what you’re speaking of; what someone feels he has to offer a woman outside of trips, fine dining, etc. The “braggers” I call them. I’m not interested in what THINGS they might include in their profiles along with pics of expensive cars, boats, etc.
    I’ve had TWO dates since March. The first being a Dr, who I felt I was beneath, because my divorce left me nearly financially bankrupt. I don’t want ANYONE thinking I’m dating them for their profession or their bank account. He indeed is an M.D. I told him I wasn’t comfortable and why. He pursued so I met him for an early dinner and drinks, (his choice). I arrived at the same time he did but had no idea of who he was when he approached me. I look just like my pics on the site. He did not whatsoever! It was obvious he’d used very old pics. I’m not choosing men by their looks, but let’s face it, we all want to be comfortable with who’s in a picture or it could possibly turn either one of us off completely. I’m a lady, and I had a pleasant time with him, although it was obvious he was pushing the income and his lifestyle at me, maybe to compensate for his photos being 10+ years old? I can’t say. He insisted on paying the bill and I thanked him more than enough, said I enjoyed meeting him and that maybe we’d talk again.
    I wasn’t interested, but said the “maybe” so as not to come off as harsh. He walked me to my car, asked if I’d like to come to his home for a couple after dinner drinks. He lives in a most elite area, and again he used that as a lure I felt. I thanked him again but said, no, it was already getting late and I have a dog at home to get back to.
    He rudely told me that my dog could wait, and that he’d just spent a very nice sum of money on me, and he would like to finish the evening at his home. A very secluded elite area. I said no, and left. That was that.
    Date #2 was a few weeks ago. Completely different person, personality. Been speaking with him by text and phone for weeks.
    Finally made a date on a Friday night. He was making a long drive to meet me. He asked that I choose a place to meet, and I did. A very nice upscale bar I’d asked him if he was interested in seeing. An achitectural splendor. He’s an architect, as well as other things. Very interesting man. I’d enjoyed our talks by phone and was looking forward to meeting him. He expressed the same feelings. We had lots in common and conversation was excellent. We had drinks and he suggested we look for a place for dinner other than where we were. I asked what he’d like and give him some ideas.
    We drove and drove in my car all around the large city I’m near. Till nearly 11:00 p.m., when he finally settled on a place that I would never take anyone on a first date. It was a hole in the wall restaurant/bar that I knew the owner personally. I kept throwing out ideas and he’d say no. We were running out of time to get dinner so I said let’s go to my friend’s place. I was exhausted driving senselessly and getting nowhere.
    We did enjoy each other’s company. Dinner was great! He loved it! Greek food. We enjoyed ourselves there, too. Talking was easy. I said I’d pay for dinner. It was cheap!
    He wouldn’t let me and I obliged him.
    By that time he wanted to get his car out of the parking garage. We drove a short way and we were there. I waited for him to come out of the garage. He did. Got out and came to my car door and said what a wonderful impromptu evening it was and that he thoroughly enjoyed me, my company and liked me a lot. We’d kissed and hugged several times that evening and it felt comfortable for both of us, I thought.
    It was 1 a.m. We’d met at 7. He leaned in to kiss me and asked if I’d like to get a hotel room. I honestly was taken back by that. I said no, I don’t. Again saying I have a dog at home regardless of what may have happened. I said I hoped we’d see each other again. He said of course and apologized if I was upset that he said that. I thanked him and asked that he let me know when he got home. It was more than an hour away. I text him the next morning to make sure he’d gotten home since I hadn’t heard from him. I had text him when I got home as he asked I do. He was glad and I thought things were ok. I would have definitely seen him again. In spite of his hope I’d go to a hotel. I liked him as a person. I was willing to overlook that and give it another shot. I never got a chance. No reply, no phone call. No text. Nothing.
    I’m 56. The rudeness of some people is to me unimaginable. I felt like trash at that point! I wasn’t good enough for a phone call telling me that’s all he had in mind? I’ll never know if it was that or what.
    It makes me not go back onto that dating site because it’s just not for me I suppose.
    When I meet someone, they’re meeting ME!
    I’m not expecting anything but common courtesy and for someone to be an adult. I’m not a child nor do I act like one or treat anyone like one. I’m still ticked about that because I really did enjoy the hours we spent together and the couple weeks prior to meeting on the phone. I’ll just assume it was only sex he was interested in. Nothing other than that makes sense to me still. Good luck with your future dates. I have followed you and believe you to be exactly as you’ve always described yourself to be. I would think any woman would find you to be charming at the very least.

    Liked by 2 people

  2. I agree and I commend you, Matt, and thank you for this article. I have no doubt that things happened just as you stated. I too, am trying to join in on the middle aged dating scene. I joined 3 years ago, but first became semi active after giving myself an ultimatum 1/1/17. I started going through the awful process of adding pics, my profile, which told things about me and my interests as a person, and what I’m about as a person. Much like you described the details of yours, Matt. Then I waited. I felt awkward and uncomfortable, especially in trying to look through profiles of men, (using tips I’d been given), on what to look for in someone’s profile especially red flags. I’ve been on 2 dates since March.
    Date #1 pursued me, and I resisted, feeling “out of my league”. His profile stated he was an M.D.
    Showed he’d been traveling the world and had a variety of pics of himself in different places. All looked fabulous, but I was not comfortable. I have a career I’m proud of, but my divorce and ex left me virtually bankrupt. Everything that should have never happened to me or anyone in a divorce, did. Unfair. Unjust. That’s my main reason for waiting nearly 5 years to start dating. Very bitter, paying off debt I didn’t incur, and felt I had nothing to bring to the table but myself. I’ve not traveled the world and felt somehow less of a person to attempt just a date with such a person. A Dr at that. He insisted and I did meet him.
    But the man I met was not recognizable from his photos. Maybe 10+ years older. He recognized me right away. I did not know it was him. He was using his status with old pics and betting on meeting someone, almost as a trap.
    I was very agitated that someone would do that at all. I’m not a shallow person, but I’m an honest one. When someone meets me they’re meeting ME, and how I’ve described myself as a person and my photos look like me. I had drinks and dinner and he insisted on paying at the place he’d chosen for us to meet.
    The evening was fine and conversation was nice, but by starting off on a lie with photos that didn’t resemble him at all was too much for me to accept.
    He asked me to have after dinner drinks at his home nearby in a very elite secluded neighborhood, trying to lure me with his stature I believe (?) I politely declined and left. In reality I know I’m “good enough” as a person with good character, sense of humor, caring, etc., and I’m told I’m very attractive by most people. I’m not seeing many men’s profiles that don’t list their wants and requirements, to be honest. I’m in a large metropolitan area in the Midwest. Many types of people. I’ve seen many profiles stating that if you don’t have yourself in a place where you’re financially stable, DON’T BOTHER! I’ve seen it often. Very boldly!
    Financial stability can be taken many different ways by many different people I’ve come to learn.
    I may not be where I’d like to be but I’m fully able to take care of myself. I’ve learned that it’s a way for men and women to advertise their “must haves” in a possible relationship or even just casual dating. I’m avoiding those altogether. It leaves few that are possibilities, because at the other end of the profile scenario, you’ve got those who tell you next to nothing, another red flag to me.
    I had date #2 three weeks ago with a man I’d been texting and had numerous phone conversations with. All very good. We decided to meet near where I live and he asked that I choose a place to meet for drinks, then we’d both decide dinner from that point.
    Enjoyed meeting him. Liked him. Comfortable with him. He said the same many times during the evening. It was an excellent first date by my opinion and he more than made me sure we’d be seeing much more of each other.
    Came time to leave and he insisted on paying after I offered to pay. I thanked him, & we left to get his car that was parked at a nearby parking garage. It was 1 a.m.
    I waited for him to come out of the garage where I was parked right next to, to say goodnight.
    He again told me how lovely I was and how much he enjoyed our evening. Kissed me and asked if I’d go to a hotel with him. My heart sank. I’m 56. Him about the same. I said no, that I wouldn’t be joining him, but hoped we’d see each other again. I did. I liked him that much that I was willing to forget that remark, thinking maybe he was nervous and said it somehow without thinking.
    (Who knows)? He said he would love to see me again soon. We kissed goodbye and each left. I never heard from him again. I even text him the next morning to make sure he’d gotten home fine. (He lived farther). No reply. Nothing.
    Three weeks and never heard from him again.
    I was upset and I think rightly so. We didn’t have an expensive dinner nor the drinks before. Plus, I did offer. I felt worse than trash after what I thought was an excellent date. My profile did not say casual dating or casual sex. It states that my desire is to hopefully find a relationship in time. That was my second and last date so far.
    I’ve not been back on the site.
    I second guess myself a lot and normally underestimate myself. But I was positive it was a terrific evening for both of us. Apparently it would have been if I’d have accepted his invitation to a hotel. Then maybe not heard from him again, as well. I’ll never know but I’ll chalk it up to a learning experience and a practice date!
    I wish you well, and we women are not all like the ones you’ve encountered, just as I know all men are not like the two I met.
    They make things look bad for all of us, and so I’ll continue to strive to be the person I am and just a little smarter on my thoughts of a perfect evening, until that evening was completely over and that had not been suggested out of the blue. Good luck to you. I’ve followed you for awhile now and like much of your writing, as well as you as a person, and this one I just had to add my own female story to show that we’re all not in it for the dinner. I’d much rather have good company than dinner anytime.

    Liked by 1 person

  3. This is sad but funny. I definitely see how women can easily do this to get a free meal. However, I have definitely dated guys where I thought the date went horrible but I didn’t want to be rude and end it early so I let the date continue on. I of course let him pay for the meal but I didn’t even think to how he might have taken it. Great read 🙂


    • I so much appreciate your honesty about you letting men pay even if. you know there won’t be another date. I think this old-fashioned custom is fine. You are not dating for a free dinner so no guilt necessary. On the other hand, you should support the notion that while men and women are equal in our culture, we have different roles in relationships.

      Liked by 1 person

  4. I love reading your posts. They always leave me more committed to my marriage. (Wherein my spouse and I take turns treating each other and I covered the tip on our first date.)


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