# Dilemma - please help (involves sex) **URL:** \ **Category:** Miscellaneous and Personal Stuff I Must Share\ **Created:** [March 30, 2002, 6:44am UTC](https://boards.straightdope.com/t/dilemma-please-help-involves-sex/100886 "2002-03-30T06:44:01Z")\ **Posts on this page:** 20\ **Page:** 1
**Author:** ![Hemlock](https://avatars.discourse-cdn.com/v4/letter/h/c5a1d2/32.png) [@Hemlock](https://boards.straightdope.com/u/Hemlock)\ **Post date:** [March 30, 2002, 6:44am UTC](https://boards.straightdope.com/t/dilemma-please-help-involves-sex/100886/1 "2002-03-30T06:44:01Z")
I knew that “(involves sex)” would get you… True story. I was with 2 friends of mine - Jim and Bob - in a bar a few weeks back. Jim’s wife turns up, having just been to the beauty parlor, with her hairdresser, Mary. Mary is very tall for her race and very striking. Almost unnaturally beautiful, and dressed very elegantly. Bob, who has a high opinion of his attractiveness to women, zeros in on Mary, who seems quite receptive. They are together for 2 hours, ignoring everyone else. Jim later tells me his wife says Mary was born male. (She and Mary are both from a culture where people are pretty laid back about this). I guess she is on hormone treatment, but Jim’s wife says she has not had a sex-change operation. Bob and Mary have since been in the bar together several times, engrossed in each other and groping, kissing etc. Bob has tried to entice her back to her place, but she has turned down this invitation. All the regulars in the bar now know about Mary, so there’s lots of snickering going on behind Bob’s back. Bob’s probably not serious-serious about Mary, but he’s obviously a bit smitten and would really like to get into her pants (or he thinks he would). He’s seriously embarrassing himself. What am I to do? I’m inclined to leave well alone and let Bob lose interest in Mary, or find out the hard way what she is/isn’t. Can I do that with a clear conscience? My reluctance to say anything is partly because I don’t want to bear bad news, and partly because he might feel terrible, knowing that others already know. And partly because other people wouldn’t forgive for ruining their entertainment. ---
**Author:** ![happyheathen](https://avatars.discourse-cdn.com/v4/letter/h/b5e925/32.png) [@happyheathen](https://boards.straightdope.com/u/happyheathen)\ **Post date:** [March 30, 2002, 8:09am UTC](https://boards.straightdope.com/t/dilemma-please-help-involves-sex/100886/2 "2002-03-30T08:09:33Z")
> [@](#): > > Can I do that with a clear conscience? only you can answer that one. me? 'tain’t my business - the onus is on Mary, not you and, exactly does WHO “KNOWS” WHAT? ---
**Author:** ![SpaceDog](https://sea3.discourse-cdn.com/straightdope/user_avatar/boards.straightdope.com/spacedog/32/9932_2.png) [@SpaceDog](https://boards.straightdope.com/u/SpaceDog)\ **Post date:** [March 30, 2002, 10:20am UTC](https://boards.straightdope.com/t/dilemma-please-help-involves-sex/100886/3 "2002-03-30T10:20:16Z")
I’m assuming from your message that you’re sure that Bob doesn’t already know this. Since Mary is Jim&Wife’s friend, and I’m assuming Jim and Bob are friends, I’d think it’d be more Jims role to have a quiet word. Your decision of what to do should be based on how embarresed/upset Bob would be if he found out know compared to if he found out later. Having said that it’s really Mary’s place to tell him, rather than yours. I’d be inclinded to have a word with Jim and strongly suggest that he gets Mary to come clean with Bob, if she hasn’t already. However if I was actually in that situation I’ve no clue what I’d do, probably post the question here. Just my two cents. ---
**Author:** ![jjimm](https://avatars.discourse-cdn.com/v4/letter/j/ba8739/32.png) [@jjimm](https://boards.straightdope.com/u/jjimm)\ **Post date:** [March 30, 2002, 10:39am UTC](https://boards.straightdope.com/t/dilemma-please-help-involves-sex/100886/4 "2002-03-30T10:39:13Z")
What a nightmare dilemma. My 2c (Euro cents of course) is: if Bob is the kind of chap to be freaked out by Mary’s true gender, then he’s going to have his mind blown sometime soon; either in flagrante, or by someone telling him. If you decide that you do have to tell him, you could go by a cicuitous route - perhaps dropping into conversation how some of this race’s men make beautiful women - “just like Mary. You didn’t know? Oh my God, I thought she’d told you,” etc. Failing that, I second the ‘have a word with Jim to have a word with Bob/Mary’ route. [sub]I’d just like to point out that the Jim and Bob in the story bear absolutely no relationship to **jjimm** , or my brother, **bbobb**.[/sub] ---
**Author:** ![Brynda](https://avatars.discourse-cdn.com/v4/letter/b/e79b87/32.png) [@Brynda](https://boards.straightdope.com/u/Brynda)\ **Post date:** [March 30, 2002, 2:27pm UTC](https://boards.straightdope.com/t/dilemma-please-help-involves-sex/100886/5 "2002-03-30T14:27:58Z")
Yikes. That is a sticky situation. Mary should tell, but if s/he won’t, you are kind of stuck. What would you want if you were Bob? Would you rather be told by a friend or carry on longer, presumably not knowing? I would want to know, so assuming you go that route, I like the suggestions given for doing so tactfully or else getting Jim to do it. As for spoiling everyone’s fun, let em find something else to do. This situation isn’t fair to Bob at all. ---
**Author:** ![Otto](https://avatars.discourse-cdn.com/v4/letter/o/bbe5ce/32.png) [@Otto](https://boards.straightdope.com/u/Otto)\ **Post date:** [March 30, 2002, 2:39pm UTC](https://boards.straightdope.com/t/dilemma-please-help-involves-sex/100886/6 "2002-03-30T14:39:52Z")
I’ve read this thread three times now and I’m unable to figure out why anyone thinks the relationship between Mary and Bob is your business or the business of anyone else. Oh, and btw, Bob already knows Mary’s “true gender.” Mary’s a woman and Bob knows it. ---
**Author:** ![cagiva650](https://avatars.discourse-cdn.com/v4/letter/c/da6949/32.png) [@cagiva650](https://boards.straightdope.com/u/cagiva650)\ **Post date:** [March 30, 2002, 2:54pm UTC](https://boards.straightdope.com/t/dilemma-please-help-involves-sex/100886/7 "2002-03-30T14:54:29Z")
My thoughts exactly **Otto** why all the whispering behind their backs-MYOB people! ---
**Author:** ![Rysdad](https://avatars.discourse-cdn.com/v4/letter/r/7cd45c/32.png) [@Rysdad](https://boards.straightdope.com/u/Rysdad)\ **Post date:** [March 30, 2002, 4:32pm UTC](https://boards.straightdope.com/t/dilemma-please-help-involves-sex/100886/8 "2002-03-30T16:32:46Z")
Ask yourself if you’d want to know, then act accordingly. ---
**Author:** ![Lamia](https://avatars.discourse-cdn.com/v4/letter/l/8e7dd6/32.png) [@Lamia](https://boards.straightdope.com/u/Lamia)\ **Post date:** [March 30, 2002, 4:35pm UTC](https://boards.straightdope.com/t/dilemma-please-help-involves-sex/100886/9 "2002-03-30T16:35:22Z")
My advice is to keep your mouth shut. It’s not really any of your business, and it wouldn’t help anyone if you said something. ---
**Author:** ![whistlepig](https://avatars.discourse-cdn.com/v4/letter/w/73ab20/32.png) [@whistlepig](https://boards.straightdope.com/u/whistlepig)\ **Post date:** [March 30, 2002, 4:41pm UTC](https://boards.straightdope.com/t/dilemma-please-help-involves-sex/100886/10 "2002-03-30T16:41:45Z")
Perhaps you could take Mary and Bob golfing. If Mary tees up on the ladies teebox - tell Bob. ---
**Author:** ![Hemlock](https://avatars.discourse-cdn.com/v4/letter/h/c5a1d2/32.png) [@Hemlock](https://boards.straightdope.com/u/Hemlock)\ **Post date:** [March 30, 2002, 4:42pm UTC](https://boards.straightdope.com/t/dilemma-please-help-involves-sex/100886/11 "2002-03-30T16:42:39Z")
> [@](#): > > \*Originally posted by Rysdad \* > \*\*Ask yourself if you’d want to know, then act accordingly. \*\* Yes, I guess that’s the answer I was looking for. I’d want to know. Tell you what I’m going to do. Send an anonymous email to Bob from “a friend of a friend” and let him know. That way, he knows, but he doesn’t know I know. Many, many thanks for the advice on this, everyone. Now, I’ll take a deep breath, set up a dummy email account and do the deed. Hate to see this guy making a fool of himself. Thanks again! ---
**Author:** ![Northern\_Piper](https://sea3.discourse-cdn.com/straightdope/user_avatar/boards.straightdope.com/northern_piper/32/5304_2.png) [@Northern\_Piper](https://boards.straightdope.com/u/Northern_Piper)\ **Post date:** [March 30, 2002, 4:56pm UTC](https://boards.straightdope.com/t/dilemma-please-help-involves-sex/100886/12 "2002-03-30T16:56:45Z")
I see. You have heard third hand gossip (Jim’s wife to Jim to you) about the personal life of a fourth person. Nothing in what you have said confrims that Mary is the source of the gossip. You want to pass this gossip on to Bob, but don’t have the courage to do it face-to-face. So you’re going to do it anonymously, the last refuge of the cowardly, the gossip-mongers, and the back-biters. I would use stronger language, but this is not the Pit. ---
**Author:** ![jjimm](https://avatars.discourse-cdn.com/v4/letter/j/ba8739/32.png) [@jjimm](https://boards.straightdope.com/u/jjimm)\ **Post date:** [March 30, 2002, 5:10pm UTC](https://boards.straightdope.com/t/dilemma-please-help-involves-sex/100886/13 "2002-03-30T17:10:01Z")
I think **Northern Piper** ’s reaction is a tad harsh, and I wouldn’t necessarily call it gossip… We’ve all seen the Crying Game. Also, it’s clear that your motivation is noble. But I personally wouldn’t take the route you’re taking. Best would be if you can get Jim and his wife to deal with it, if you feel that Bob should know. ---
**Author:** ![Billy\_Rubin](https://sea3.discourse-cdn.com/straightdope/user_avatar/boards.straightdope.com/billy_rubin/32/3622_2.png) [@Billy\_Rubin](https://boards.straightdope.com/u/Billy_Rubin)\ **Post date:** [March 30, 2002, 5:19pm UTC](https://boards.straightdope.com/t/dilemma-please-help-involves-sex/100886/14 "2002-03-30T17:19:25Z")
Maybe Bob knows. b. ---
**Author:** ![erislover](https://avatars.discourse-cdn.com/v4/letter/e/71e660/32.png) [@erislover](https://boards.straightdope.com/u/erislover)\ **Post date:** [March 30, 2002, 5:50pm UTC](https://boards.straightdope.com/t/dilemma-please-help-involves-sex/100886/15 "2002-03-30T17:50:54Z")
Hmm. This reminds me of an Ally McBeal streak of episodes, except that this Mary hasn’t had an operation yet. Although, neither did the “girl” in Ally… she did have boobs, though, I think. At any rate, I remember the whole spiel in the show was “to tell or not to tell” and the woMAN in Ally was definitely on the “not tell” side. I think that telling is something one should do, except for all the good reasons that there are not to tell. In this case, the person probably wouldn’t tell, and Bob would _need_ to hear about if from a third party. Which is a shame, he might be genuinely smitten, but either way I think he will be hurt. Maybe not, I sometimes overestimate the capacity of others to feel. I think the anonamous email is the way to go here, too, lest we replay The Crying Game. FWIW it wouldn’t bother me one bit, though I would really prefer the sex change over the not-yet-cut. If I am smitten, I am smitten. Though I would really prefer to know up front. ---
**Author:** ![Hemlock](https://avatars.discourse-cdn.com/v4/letter/h/c5a1d2/32.png) [@Hemlock](https://boards.straightdope.com/u/Hemlock)\ **Post date:** [March 30, 2002, 6:01pm UTC](https://boards.straightdope.com/t/dilemma-please-help-involves-sex/100886/16 "2002-03-30T18:01:33Z")
**Northern Piper** - it’s not gossip. I know a “Lady Boy” when I see one. Unfortunately, Bob doesn’t. If I tell him face-to-face he will LOSE face. Big time. It’s best if he doesn’t know that I know. **jjimm** - it’s as much my business as Jim’s and Jim’s wife’s. We’re all pals. Jim is taking cruel pleasure in this (as are all the other regulars in the bar), and his wife doesn’t see the big deal (all the guys here are Westerners, the women aren’t). **Billy Rubin** - Nope. I know Bob well enough to know he wouldn’t be interested in a transexual (they’re not uncommon in this part of the world, but Bob apparently hasn’t come across one before - or is naive/vain enough to think she’s kosher). God I wish we had a webcam set up in this bar! But too late now. I’ve sent an email under an anonymous name. It says… "\*Hi - This is from a regular at [bar]. I got your email from another regular. I’ve seen you with [Mary] , the tall [girl of a particular ethnic origin]. There’s something you should know… [She’s] a guy Just want you to know. No need to reply - I’m dumping this email account now.\* Phew! Well, I hope I’ve done the right thing. Yeah, I’d normally keep out of it. But I hate to see this guy humiliate himself any more. ---
**Author:** ![Lamia](https://avatars.discourse-cdn.com/v4/letter/l/8e7dd6/32.png) [@Lamia](https://boards.straightdope.com/u/Lamia)\ **Post date:** [March 30, 2002, 6:25pm UTC](https://boards.straightdope.com/t/dilemma-please-help-involves-sex/100886/17 "2002-03-30T18:25:13Z")
> [@](#): > > \*Originally posted by Hemlock \* > \*\* > Phew! Well, I hope I’ve done the right thing. > > Yeah, I’d normally keep out of it. But I hate to see this guy humiliate himself any more. \*\* There is no doubt in my mind that you have done the wrong thing, and your lack of concern or even basic respect for Mary is very troubling. ---
**Author:** ![jmpride62](https://avatars.discourse-cdn.com/v4/letter/j/c37758/32.png) [@jmpride62](https://boards.straightdope.com/u/jmpride62)\ **Post date:** [March 30, 2002, 7:21pm UTC](https://boards.straightdope.com/t/dilemma-please-help-involves-sex/100886/18 "2002-03-30T19:21:08Z")
I admit to wondering about guys who claim not to know that they are with transsexuals. It just seems to me that you can always tell, and if they are groping like you say, well… ---
**Author:** ![Wikkit](https://avatars.discourse-cdn.com/v4/letter/w/c0e974/32.png) [@Wikkit](https://boards.straightdope.com/u/Wikkit)\ **Post date:** [March 30, 2002, 10:04pm UTC](https://boards.straightdope.com/t/dilemma-please-help-involves-sex/100886/19 "2002-03-30T22:04:05Z")
> [@](#): > > \*Originally posted by Lamia \* > \*\*There is no doubt in my mind that you have done the wrong thing, and your lack of concern or even basic respect for Mary is very troubling. \*\* What a load of crap. Your opinion is that a person doesn’t even have the right to know what sex their object of courting is? If that’s unnecessary information, I’m going to start selling myself as a thirty year old billionare and world traveler. If ‘Mary’ is playing fair and has told the guy what the situation is, and he doesn’t care, then there is no harm in the e-mail. If, however, she’s been lying to him (even if it’s a lie of omission), then I don’t see why she’s the one not being respected. Ben ---
**Author:** ![Marley](https://avatars.discourse-cdn.com/v4/letter/m/ed8c4c/32.png) [@Marley](https://boards.straightdope.com/u/Marley)\ **Post date:** [March 31, 2002, 5:24am UTC](https://boards.straightdope.com/t/dilemma-please-help-involves-sex/100886/20 "2002-03-31T05:24:51Z")
> [@](#): > > \*Originally posted by Hemlock \* > **Northern Piper - it’s not gossip. I know a “Lady Boy” when I see one.** How do you know? Unless you’ve seen evidence, or you’ve heard about it directly from Mary, you are operating from gossip. “Just knowing” isn’t proof–my mother “just knows” that the data on a CD is on the label side. No amount of evidence will change her mind. Women can have all sorts of features that would be considered masculine. We can be tall, muscular, hairy, have a deep voice, whatever. I’ve seen a woman with an Adam’s apple. Maybe the gossip is true. Or maybe you’ve just ended a good relationship and destroyed a woman’s reputation. (How does one refute an accusation like that? Undress in public?) If it’s true, Mary should have been the one to tell him. [Next page](https://boards.straightdope.com/t/dilemma-please-help-involves-sex/100886.md?page=2)