Is He The Good Guy He Thinks He Is?

Name: Chad

Question: Crossed-Lines Confusion:

I’m a newly-single male, recently divorced, 39yo /w 2 children.  I have been dating casually for about 6 months.

I met Tinder Girl #1 (let’s call her Laura) a couple of months ago.  We’ve gone on two very informal dates, although both ended with shack-ups (no sex).  We’re on the same page regarding casual dating and she’s made it clear she has no interest in children.

Although there is no real long-term potential with Laura, we have fun together. She invited me for a weekend getaway to a beach house in a small town near where I live, and we scheduled it for a month or so in the future.  We text maybe once or twice a week.

Soon after, I meet Tinder Girl #2 (Tracy) who has much more potential than Laura.  She’s family-oriented (2 kids herself), much more my type, and we’ve hit it off pretty well.  We’ve gone on two very good dates, both dinners with some kissing and not much else.  She is much more conservative than Laura, which is fine by me.

Tracy is in the latter stages of divorce, so we’ve agreed that “taking it slow” is the best approach, although she did say she only dates one guy at a time.  I could certainly see our relationship progressing at some point in the future, but we certainly have not had the “define the relationship” talk, and if we did I would insist on keeping things casual at the very least until her divorce is final.

The kicker here is that I’ve determined through my master sleuthing skills that Tracy lives very, very, very close to where my weekend excursion with Laura is planned.  This town very small with little downtown area and beach, which I know Tracy frequents, so it’s very possible that I could run into her while on my weekend getaway which is two weeks away.

Although Tracy isn’t my girlfriend, I can’t help but think an encounter would be problematic.  We’ve been seeing each other every other week or so, and talking somewhat frequently, so an explanation of why I can’t meet-up in two weeks will at some point be needed.  I don’t want to lie to her but not sure I owe her an explanation at this point.

The way I see it I have 4 options:

1:  Explain the situation to Tracy, saying the plans were already in-place before we met but I don’t want to throw a wrench in our situation (probably douchey)
2:  Explain the situation to Laura and offer alternate plans somewhere else (definitely super-douchey)
3.  Cancel plans with Laura, saying I’ve been dating someone new.  (I really hate cancelling on anyone, don’t think I ever have.)
4.  Tell Tracy I’m going out of town with a friend, go on the excursion, be paranoid the whole time, and try to sort things out later if things end in catastrophe.

I guess this situation is a natural phenomenon when it comes to casual dating, and the last thing I want to do is hurt anyone’s feelings.  But it looks like that might be unavoidable at this point.

Any suggestions?
Age: 39

The easy solution, of course, is to choose one of the women to focus on at a time. But then, where’s the fun in that? Here’s another dude who’s uneasy with the “less conservative” woman, but who sees nothing wrong with a woman who isn’t even legally divorced engaging in a serious relationship. Like, what? Unreal. Tracy still technically has a husband and yet you’re already willing to go all in on her. Laura made the crucial mistake of taking you home – a decision you participated in equally – and she’s being judged for it. Okay. Cool. Cool Cool Cool. I love these newly divorced guys who enter the 2016 dating scene  still expecting women to be wearing corsets and carrying parasols.

Why are you imagining wild scenarios that will probably never happen? You don’t need to explain your whereabouts to Tracy. All you have to say is that you have plans that weekend. No need for specifics, just say you have plans. You don’t have to say anything else, nor are you required to. If you see Tracy, cross the street. Avoid her. Do what you can not to let her see you. That chances of you two crossing paths are very slim. There. Simple. If you two do run into each other, oh well. Thankfully you’re both adults and have agreed that you are not exclusive.  If either of these women freak, well,  at least you’ll see their true colors.

If you feel compelled to cancel your weekend away, just cancel plans with Laura and say something suddenly came up. It worked for Marcia Brady. Why are you immediately jumping to spilling your guts to Laura when there’s no need to? You’re creating drama for a reason, so what is it? Nobody willingly invites this kind of conflict into their lives. They just, you know, keep their mouths shut. You don’t seem to want to do that.

I guess this situation is a natural phenomenon when it comes to casual dating, and the last thing I want to do is hurt anyone’s feelings.  But it looks like that might be unavoidable at this point.

None of this is a “natural phenomenon.” None of it. I know guys who date women who live on the same block who don’t over-think like this. Hurting someone’s feelings is totally avoidable if you just keep your mouth shut. How is this even a question? Just shut it and go on your little trip and nobody will be the wiser.

You’re so busy spinning your wheels trying to convince yourself that you have the best intentions for both of these women, but do you? I mean, do you really?  It’s like you’re dying to spill the beans that you’re dating two women. Why? Maybe you just want to test these two women to see how much they like you? Maybe you just really enjoy being the meat in this dry, unsavory sandwich? Whatever has you considering being honest isn’t motivated by concern for them. I don’t necessarily believe you’re trying to avoid people’s feelings. I think you’re relishing in this situation.

Just keep your mouth shut and you’ll be fine.


Sometimes the love of your life is the love of your life. (R)


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20 Responses to “Is He The Good Guy He Thinks He Is?”

  1. JayD Says:

    No. He is not the good guy he thinks he is.

  2. Tinker Says:

    I didn’t get any sense of slut shaming from him. Just realizing that Tracy could have potential while Laura, for reasons completely unrelated to sex, doesn’t. If anything I think he mentioned their hooking up because that’s what guys do when relating a story involving a date.

    • The D-man Says:

      Same here. The guy has only been dating for six months and, unless he cheated on the ex, is not used to hiding things. I don’t think he’s looking for drama. He’s just trying to figure out the best way to approach this. Which IMO is commendable.

      • Chad Says:

        Thanks guys. Yes zero slut-shaming here, I had a great time with Laura and make no judgements- just pointing out the extent of our relations. And I do sometimes over-analyze things.

        If I were going out in a different city it’d be a non-issue (and has been), but this town has like a 5-bar downtown area that Tracy frequents and where I know Laura wants to go- so it’s a bit freaky.

        It sounds like the consensus is to just jump in and swim, and that’s probably what I’ll do.

        • Bill Says:

          “Although there is no real long-term potential with Laura, we have fun together.”

          Chad, you are recently divorced, you have no real long-term potential with anyone at this point. Period. And, you need to get it through your head, ASAP, that you are SINGLE! Quit acting and thinking like a married man who has to explain every movement he makes (to someone he isn’t having sex with).

          Options 1-4? None of the above.

          First, what on earth are you waiting for with Laura? Two months, slept together without sex twice, what-the-what? Why haven’t you had sex with Laura? If you don’t want to, then let her go and move on. If you do, then what are you waiting for? Jezuz, what does she need to do to get laid, take you away for a weekend? Ok, yeah, yikes!

          Second, why are you even seeing Tracy? Do you really need a platonic dinner companion? (answer: no, quite the opposite) Didn’t you just spend the last couple years with a woman who had little to no intention of sleeping with you? (answer: very likely yes) Let Tracy go… she isn’t ready to date, not even casually. You need to do “single you” for awhile, not a remix of old married you.

          • mxf Says:

            When I got out of a super longterm relationship, it took me awhile to get out of the owe-someone-an-explanation mode. I remember that the first guy I briefly dated wanted to hold my hand when we were out in my neighborhood, and my very first thought was “what if someone sees us and tells my ex about it,” even though my ex was the one who initiated leaving. Cringe.

            It’s tough to stop feeling so accountable to another person, but it feels excellent when you get used to answering more to yourself again.

          • Parenting Says:

            You are calling Laura a sexless prude who needs to be dumped after just TWO(!!) sexless dates which the OP enjoyed and included some making out. Jeez!

            • Parenting Says:

              I meant Tracy not Laura.

            • Bill Says:

              Tracy is still married which brings it own whole bag of worms. IMO, that alone means she is not ready for dating, probably not even casual dating. But, she is looking for more than the casual dating that the OP is looking for… so she’s the wrong person, wrong time.

              Given his recent divorce, he’s not ready for “serious” dating, and neither is Tracy, she’s still married.

  3. Sarah Says:

    #4 ftw!

  4. Glazer Says:

    Ya know? I think lying when dating is smart in the early stages.

    Nobody needs to know who is shagging who or when unless the exclusive talk comes up.

    That being said, I only sleep with one gal at a time.


  5. Coffeestop Says:

    He wants to screw the one chick as entertainment until the other chick gets her divorce, my guess is he contunes seeing both.

    • Chad Says:

      Yes! And see other women as well. I thought having these two live 1.5 hours apart was enough separation to keep those worlds apart but no such luck.

    • Eliza Says:

      Yep–agree with Coffeestop – very well put. What nonsense about “afraid of hurting anyone’s feelings”. Please…just afraid of getting caught and considered a “douche” by both women. Change plans with Laura to a more remote area. There…problem solved.
      Not rocket science.

    • Bree Says:

      Exactly. So no, he’s not the nice guy he thinks he is.

  6. Bostonette Says:

    He had it right in his “numbered bullets” “douchey”

  7. Nia Says:

    I also think it’s a bit of a player move to continue to see Laura when you know she’s not GF material, for whatever reason, unless she’s explicitly told you she’s seeing other people, not interested in something serious (and her actions back this up and I don’t mean the late night cuddle fest on the first date).
    I’m a little taken aback that the OP agreed so enthusiastically to “he wants to continue to screw one chick while waiting for the other to get her divorce”—um, what? What if the situation were reversed? What if some woman was “using” you for free meals while she waited for Prince Charming to finish a really hectic work schedule or deployment overseas?
    That’s not really dating in good faith.
    The situation is like a second-tier sitcom where the whole dramatic arc could be resolved with one quick, direct conversation: “Laura, where are we at? Are we seeing other people? No? Oh crap. Yes? Okay, cool, just checking in.” Or, like Moxie said, don’t say anything and see how it all plays out.

    • Yvonne Says:

      The comedy part happens when he’s with Laura at the bar. He gets up to go to the bathroom and…runs into Tracy as she walks in with her girlfriends. How to explain why he’s there and with whom! Queue dramatic music: dun, dun, dun!

  8. D. Says:


    I’m a bit late to this party, but one thing I’d point out in terms of how you approach dating in the future is that much of what you may think is “the right thing to do” is actually more about your sense of yourself than about what’s actually best for the other person.

    The notion of telling either or both of these women about the other, for example, may be what you think is “the right thing to do” in some absolute moral sense. But ask yourself how much of that is genuinely about concern for the other person, and how much of it is about concern that the other person sees you as a “good guy.” Or for that matter, how you see yourself as a “good guy.”

    You may think “a good guy would do XYZ” (in this case, tell the other person that he’s dating someone else at the same time). But, in fact, telling the other person will likely only serve to hurt them. This is especially true in early dating when you aren’t exclusive. The simple fact is that everyone knows (or should know) that until you’re exclusive, anyone you’re dating may well be dating multiple other people at the same time as they’re seeing you.

    The unspoken social contract, though, is that you don’t volunteer that information. Much the same way you wouldn’t say “Just so we’re clear…this is a one night stand, right?” right before you get down to business when you’ve literally met the other person an hour ago at a bar and are now home in their bed. Even if that’s what a “good guy” would do (in your mind), in fact it’s needlessly hurtful and mostly just about assuaging your own sense of guilt.

    I’d argue, in fact, that your desire to be the “good guy” — especially when coupled with what will likely be hurtful actions — is fundamentally selfish. In other words, by doing what a “good guy” would do, you’re actually just being an asshole. And it is, in fact, kinder and more socially appropriate to do the opposite (even if that matches what you think an asshole would do).

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