“He Took Me To a Casino For Six Hours on Valentine’s Day And Didn’t Even Give Me a Card!”

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I recently started dating this guy, Jack, whom I’ve known for a few years. I’ve been divorced for four years and have one child, and he is separated but still legally married (they are not separated because of me). His ex has taken their kids and moved to another state. He says the divorce is definitely happening.

Lately, we have been spending lots of time at the casino. I never would think of going to the casino as fun or date-worthy, but, in an effort to get to know Jack (in his comfort zone), I have gone to the casinos with him quite a bit. He also goes by himself when I can’t make it. He actually goes almost daily unless he has to work, has to go to a meeting, or has an obligation that he can’t miss. We go to the casino to avoid being in public while his divorce is pending.

Recently (last month), we slept together for the first time. I had been holding out but finally gave in. Last week we had a hot night of passion (our second time) leading up to Sunday, aka “Valentine’s Day.” He asked me more than once, “What do you want for Valentine’s Day?” I was pleasantly surprised that he cared. We were newly dating, so I thought I better not ask for anything ridiculously lavish and that it should be something we both could enjoy. So, I asked for a specific type of flower and lingerie. A couple of days later (this is still pre-Valentine’s Day), we discussed my size. Then when we slept together last week, he said he was having a hard time finding the lingerie. I said, “I have faith in you.”

Well, as you’ve probably guessed, on Valentine’s Day I got no flowers, no lingerie, not even a card. We ended up going to the casino (I even wore a pretty red dress) and had a steak dinner that he was able to comp. I was nice the entire six-plus hours we were there, even after telling him I was ready to go (it was after 10PM on Valentine’s night). On the way home, I told him that I was upset and he said that I was “beating a dead horse.” When we got to my car, I pulled out the Valentine’s Day card that I had bought him, slid it over to him, got out, and ran to my car. I was so disappointed.

I don’t know what to do. He texted and called me the next day. I texted back once, but now I have his number blocked. I am upset because of his lack of effort on Valentine’s Day after bringing it up to me several times and because of my seemingly bad judge of character in a man/partner. Please help me. — Bad Judge of Character

It’s interesting that it would be Jack’s lack of effort in buying you lingerie that finally broke the camel’s back and not, say, that he gambles every day, that he doesn’t take you out on real dates, and the little fact that he’s still married and wants to hide you away while his “divorce is pending.” It’s too bad that, as a grown woman, and a mother, and someone who has been married once before, you would need something as silly as Valentine’s Day to help you judge Jack’s character and intention. But, now you know. The guy’s a joker, he doesn’t care about you, there’s no future there. That’s the bad news. The good news is there are other men! And, luckily, this one was already married so you didn’t get yourself tied up to him legally and it should be very easy to MOA.

Now, going forward, since you say you’re a bad judge of character, I want you to refer back to this little list I’m going to share with you to help you quickly determine whether someone isn’t worth pursuing. Here we go:

A Few Signs He Isn’t Worth Pursuing*

1. He doesn’t want to be seen in public with you.
2. He has a clear and unhealthy addiction that affects his emotional and physical availability (to gambling, alcohol, drugs, porn, etc.).
3. He won’t tell you where he lives/you’ve never seen his place.
4. He won’t introduce you to anyone important in his life (friends, family, close colleagues, etc.).
5. He’s mean to your kids, family, friends, or pets.
6. He’s mean to you.
7. It’s been more than a handful of dates and he hasn’t kissed you yet.
8. He only calls or texts late at night.
9. He calls his exes nasty names and blames everything on them.
10. He has called you nasty names.
11. He has hit you or has touched you in an aggressive, unwelcome way.
12. He has kids, but he doesn’t have a relationship with them.
13. He promises you things but doesn’t deliver.
14. He borrows money all the time.
15. He pays you to play tennis with him.
16. He nags you to lose weight or criticizes your appearance.
17. He takes photos of you in a sexual way while you’re asleep/ without your consent.
18. He tried to have sex with you while you were asleep.
19. He makes you sleep on a yoga mat while he takes the bed.
20. He told his co-workers that you’re his hooker.

*This is not an exhaustive list!


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If you have a relationship/dating question I can help answer, you can send me your letters at wendy@dearwendy.com.


  1. Wendy, I am a joker, and I take umbrage at being lumped in with this dude. The proper gambling-based term for him is knave. His name wouldn’t be “Jack,” would it? Everything else you said is spot on.

    1. Avatar photo Raccoon eyes says:

      For some reason, that triggered me to start singing “50 Ways to Leave Your Lover” in my head. …Just slip out the back, Jack; make a new plan, Stan; you dont need to be coy, Roy…

  2. wow, if there was ever a need for acronyms like MOA and DTMFA, well here it is.

  3. dinoceros says:

    At least you recognize that you’re a bad judge of character. I think something that people misunderstand is that they think simply going on a couple of days with a crappy person means you’re a bad judge of character. The real issue is continuing to date them. Crappy people are not any different from other people in that they often also want great people. I had a friend who was convinced that because weird guys approached her, it must mean that she’s weird. Well, no, weirdos can like awesome people, too. Her issue was that she continued to see them even after learning that they were awful.
    So, my question for you is did you notice all these red flags and ignore them or try to explain them away? Or did you convince yourself that they weren’t red flags? Or did you not even notice them? That’s something to think about because not spotting them and spotting them and ignoring them are two different things. As if this were a “find the differences between the pictures” game, the red flags I see immediately are his apparent gambling addiction, the fact that he’s not officially divorced, and the fact that you can’t go in public with him. Did you see those and realize those are red flags? Did you not care? Did you assume that he was different? Finding that out will help you figure out what you need to work on for the future.

    1. That’s what I’m not getting here. I don’t even think you can even call this being a bad judge of character. There was no judging required, this guy’s character flaws couldn’t have been more obviously on display if they were written in neon on a billboard.

      At first I thought that the fact that he takes her to the casino to avoid being seen in public with her before the divorce is final was a lame excuse to hide the fact that he had another girlfriend, or wasn’t really separated from his wife. I mean, that’s nonsense. I met my boyfriend more than a year after his separation, we started dating a few months before the divorce was final, and he wasn’t remotely concerned about being seen in public with me.

      But now I’m not even sure that’s the case. I think it’s all part of his gambling addiction. I think the story about not wanting to be seen in public is the lame excuse, to cover the fact that he can’t bear to be away from the casino.

      Whichever is the case, you knew from the get-go that he had a gambling addiction (yikes), and he told you that he didn’t want to be seen in public with you (grossly insulting, regardless of the reason). Did you not mind those things about him?

      1. dinoceros says:

        That’s a good point about using that excuse to cover his gambling addiction. I hadn’t even though about that, but it makes a lot of sense!

  4. Avatar photo Raccoon eyes says:

    LW, seriously, WWS. Im actually not even sure what you are asking Wendy, but I do know she gave you a spot-on answer. Stop all the woe-is-me boo-hooing and just be glad that you avoided this.
    Im honestly surprised at whatever it may have been that finally convinced you to go cold-turkey on this guy, but chucking him to the curb was definitely the right choice. I mean, any guy willing to take you out in …errr, public, is a step up from this guy. (I dont understand why a casino is not public, especially considering his wife up and moved the rest of the family to another state….but whatever. Again, not the most confusing aspect of this, but strange.)

  5. If you are not a gambler, why wouldn’t you have considered it a red-flag, deal-breaker moment when the third ‘date’ he took you on was yet another casino visit. If you delayed, what caused you to finally sleep with him as this same red flag kept reappearing. Yes, you have bought into all the Hallmark advertising of ‘special days’ that have to be honored in certain ways, but if meeting the Hallmark expectation of special days covers for day-to-day crappy treatment in your mind or, worse yet, could cancel out day-to-day great treatment, then I question your values.

  6. Another Jen says:

    I don’t mean to be a drama queen, but I speak from personal experience. This man shows all the signs of being a gambling addict. Run far, and run fast. He absolutely will drown himself and, if you hang around, he’ll absolutely take you with him. I’m talking about emptying your bank accounts, opening credit cards in your name, dragging you and your family into dealings with shady bookies and illegal betting. A comped dinner at a casino for Valentine’s day is a the least of your worries. Seems like his ex(?) got smart and got out. Seems like you’ve put a bit of distance between you…keep going, never look back.

  7. LisforLeslie says:

    So so so many red flags but I have to ask: How is going to a casino “not being public”? It sounds like it’s just an excuse to go to a place he wants versus somewhere he can’t gamble. You need to run fast and far and ask yourself why did you dismiss all of these red flags? Why don’t you respect yourself enough to demand more, not in terms of gifts but in terms of behavior?

  8. Monkeysmommy says:

    So, a few things here- first, it sounds like the guy is a great, big loser, and you should cut your losses. But with that in mind, let’s examine things from your letter: you asked for flowers and lingerie from a guy you just started seeing. That is kind of weird to me, and I am guessing he thought so as well, seeing as how he tried to tell you he was “having trouble finding it”. I don’t think he was looking for your faith in him, but more likely wanted a pardon. Now had you asked for just a card, would you have gotten it? Probably not. But still, lingerie is way too personal for a guy you rolled in they hay with twice. Even if you did know him for three years. My advice would be to stop sulking like a spoiled brat (you blocked him? Are you 16?) and move on. I am not saying that there aren’t guys who deserve to be blocked and all, but you sound more like you are just trying to punish Rain Man over there, and it isn’t flattering.

    1. i’m with you on this. i know the dude has his imperfections, insensitive and irresponsible in some ways. but i also find your way of reacting is childish. at some point, it felt like you are too materialistic to react that way. and you sounded like your justifying your needs. i feel you – it’s upsetting/disappointing that your bf behaved like that. but then, you could be a better wiser person how to handle it.

  9. mangomama says:

    Add one to the list:
    21. He is married. (Divorce “pending”, being separated etc = still married= not available.)

  10. Another Jen says:

    Hi! The high frequency of the casino visits is a huge red flag. My ex-husband had a similar casino habit and it turned out that was just the tip of the iceberg…illegal betting, maxing out cash advances on credit cards I didn’t know about, diverting a portion of his paycheck into a secret account.

    Think about how much money is likely flowing out of his pockets an into his gambling habit.

    I’d say run far and fast…but if you’re not ready to make that call, PROTECT YOUR FINANCES! Keep an eye on credit card balances, keep a watch on your credit report to ensure accounts aren’t being opened, don’t share your account passwords.

    Best, AJ

  11. This man is married with a gambling problem. NEXT.

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