Douglas Silver

You are not Magellan

Dear ‘I Must be Crazy’:

Let me start by thank­ing you for your email. I applaud you for rec­og­niz­ing a dif­fi­cult sit­u­a­tion. You find your­self in unfa­mil­iar ter­ri­to­ry, and rather then sev­er­ing ties out of fear, you’ve sought out pro­fes­sion­al advice. Bravo!

To the issue at hand, I’m curi­ous as to why you believe the woman you have a date with used to be a man. As a gen­er­al rule, it’s bad form to look into someone’s back­ground before meet­ing her. I’ve said many times in this col­umn, the Internet is a dan­ger­ous resource for idle minds. Granted, you met her online, but that doesn’t enti­tle you to stick her name in a Google Search and click I’m Feeling Lucky.

That aside, your dif­fi­cul­ty uncov­er­ing specifics as to the woman’s past shouldn’t nec­es­sar­i­ly raise red flags (we don’t all strive for Search Engine Optimization). While you’ve told me noth­ing that seems to val­i­date your bizarre belief, for argument’s sake, let’s say you’re right: The woman you’re see­ing is trans­gen­der. No one would fault your hes­i­tance. There’s the obvi­ous con­sid­er­a­tions of sex­u­al­i­ty and comfort—both yours and hers. Certainly, you would deserve full dis­clo­sure before the rela­tion­ship esca­lat­ed to any lev­el of phys­i­cal or emo­tion­al inti­ma­cy (con­sid­er this a new rea­son not to kiss on the first date). But under­stand, I don’t fault this woman for not reveal­ing any­thing to you—if, in fact, there’s any­thing to reveal. First dates should be infor­ma­tive, but light. It’s a test dri­ve, pos­si­bly the first of many. From the tone of your email, I dis­cern an air of resent­ment. And while I com­mend you for seek­ing out my advice, with the sug­ar comes the med­i­cine: You have no right to be angry.

Bear in mind, if this woman did com­plete gen­der reas­sign­ment surgery it was the cul­mi­na­tion of years of ther­a­py and a pos­si­ble iden­ti­ty cri­sis. Her gen­der iden­ti­ty may very well over­lap with her secret iden­ti­ty, i.e. those facets for which she still fears being judged. Make no mis­take: this woman is a woman even if she was once a man. The courage it took for her to come to terms with her­self is hero­ic. I hope you’ll remem­ber this as you decide whether or not to move for­ward with the relationship.

Sincerely Yours,

Dotty Kay
Kay Marks the Spot

Dear Third Date Approaching:

Listen up, sweet pea, I don’t know where and by whom you were raised, but in the real world, a gen­tle­man doesn’t per­form a pro­fes­sion­al back­ground check on a woman he’s dat­ing. How would you feel if after two dates a lady made it a point to go through your clos­et and dig out every pair of dirty draw­ers that ever graced your rear-end? I know you emailed my col­umn because you’re wor­ried that this woman popped out of her Mama’s oven as a man, but sweet­heart, as I see it you have a far more seri­ous prob­lem: Your inabil­i­ty to open­ly com­mu­ni­cate with a poten­tial lover, not to men­tion your imma­tu­ri­ty toward a painful­ly sen­si­tive issue.

And for all your crack­er­jack PI work, what have you uncov­ered? Apparently, you’re dat­ing a suc­cess­ful civ­il rights attor­ney who moved to New York to enter pri­vate prac­tice. So what, she legal­ly changed her name a few years ago. Do I have to list all the legit­i­mate rea­sons why some­one might do this? It doesn’t mean she changed any­thing else about her­self. As for the old online bio you stum­bled upon, I think you’re mak­ing hay out of crab­grass. You’re telling me that there’s an LGBT lawyer in Los Angeles with the same last name and sim­i­lar first name as the woman you’re dat­ing. Level with me now, what’s “sim­i­lar”? Both names start with the same let­ter? How com­mon is her last name? I’m sor­ry gum­drop, but just because you can’t get in touch with this lawyer in LA doesn’t mean you’ve unearthed the Holy Grail. After five years, it’s more like­ly he found a new job or moved (not to New York). I know you think the man’s pho­to bears an “unde­ni­able resem­blance” to the woman you’re dat­ing, but I’m not buy­ing it. Don’t talk to me about hair col­or or bone struc­ture or that freck­le they both have above their tra­chea. As my pap­py used to say, A man plants enough seeds and he’s liable to see trees even in a clearing.

Just to be clear, you know that many lawyers who work on behalf of LGBT rights are nei­ther L, G, B, or T? Do you think that all immi­gra­tion attor­neys were once immi­grants? Or that a land­lord-ten­ant attor­ney must have been born a building?

I don’t mean to poke fun at you, but I can’t believe some of the hare­brained antics you’ve dreamed up. Do you real­ly think it’s a good idea to chal­lenge this sweet lady to a series of tongue twisters? Now I’m no speech pathol­o­gist, but I don’t think “Hard R’s”, as you call them, make an Adam’s apple more pro­nounced. And come now, sug­ar, a mouth­wash gar­gling con­test? Any man with sense enough to write me should know bet­ter than that. But in case I’m wrong, I strong­ly rec­om­mend against telling her that your book club plans to read Middlesex just so you can gauge her reac­tion. (Note: you might want to sit down with that trusty Internet you like so much and learn the dif­fer­ence between trans­sex­u­als and hermaphrodites.)

If you think I’m tak­ing a harsh tone, it’s only because there’s some­thing so darn frus­trat­ing about your email. You speak so earnest­ly about want­i­ng to be in an open, hon­est rela­tion­ship. Then you go off talk­ing about this scheme and that one, like you’re a lit­tle boy play­ing detec­tive. If you’re so uncer­tain about who she is, why see her again? Why heap extra vine­gar on to this pick­le? I’ll tell you why: You feel some­thing for this woman. Based on your descrip­tion, I have a hunch she’s every­thing you’re look­ing for. Now I can’t help but won­der if you don’t think you’re ready for her?

You men­tioned that you’re “recent­ly” divorced. How recent­ly? Is it fair to say that this is your first seri­ous prospect since you’ve re-entered the sin­gle life? It’s a scary place, no doubt about that. We all know how fear can go to town on the mind. Otherwise rea­son­able peo­ple jump to wild con­clu­sions; you hear hoof beats and sud­den­ly you expect zebras instead of horses.

Listen to me now, because I do want the best for you. Consider what’s get­ting you so riled. Why do you even care if she was once a man? I’m not ask­ing because I don’t think it mat­ters (it cer­tain­ly would to me). But what are your rea­sons (objec­tions)? If you pur­sue this rela­tion­ship, are you con­cerned that you’ll have to reassess your own sex­u­al­i­ty? Remember, you’re talk­ing about anoth­er human being, one whom you obvi­ous­ly care about or you wouldn’t be wrack­ing your brain six ways from Sunday to fig­ure out.

I’m all for you learn­ing about this woman, but do it the right way. Learn from her. Let the rela­tion­ship play out at a pace you both can han­dle. Remember, a third date doesn’t have to end search­ing for your box­er shorts and won­der­ing if you have time to go home and show­er before work.

With love and understanding,

Debbie Debbie
The Deb-utante

Dear Sleeping with the Light on:

No, a “freak­ish­ly large” cli­toris does not indi­cate a woman is trans­gen­der. Clitorises, like penis­es, come in a range of sizes and shapes; that your lover’s is par­tic­u­lar­ly notable shouldn’t be cause for con­cern. Consider your­self lucky that you’re far less like­ly to miss the bull’s eye. Though, your ques­tion begs two on my part: Why are you so adamant to believe that your lover was for­mer­ly a man? And, in the absence of this assur­ance, why are you main­tain­ing sex­u­al relations?

The lev­el of com­pas­sion she’s exhib­it­ed toward you bor­ders on the super­nat­ur­al. If I under­stand cor­rect­ly, she has encour­aged you to mend your rela­tion­ship with your daugh­ter, a laud­able sen­ti­ment by any stan­dard. She rewrote your resume so that you might find a job you enjoy. She has even offered to let you stay with her before the judge allo­cates assets to your ex-wife. Forget trans­gen­der, I rec­om­mend you call the Vatican and see if they’re miss­ing a saint.

Is it pos­si­ble that you’re con­coct­ing an issue on her part so your recent mis­for­tunes seem less glar­ing? It’s dif­fi­cult to fath­om that you could still be “in the dark” on this mat­ter if it was at all root­ed in fact. You have met her close friends. Your friends adore her. You admit, when you’re not ques­tion­ing “what she might have been”, you’re hap­py. With that in mind, why would you ask to see her prom pho­tos or inquire as to her favorite junior high school fads? Are you real­ly com­fort­able hold­ing the view­point that sleep­ing with a Cabbage Patch Kid fore­shad­ows one’s future sex­u­al­i­ty? Do I real­ly need to point out that own­ing a Culture Club CD is not a sure sign of a “life­time mem­ber­ship in the LGBT com­mu­ni­ty”? Such beliefs are not only offen­sive, but are so clear­ly a macho attempt to mask the greater issue at hand, i.e. your feelings.

It doesn’t take a PhD to rec­og­nize that for all your mus­ings and art­less strat­a­gems, you’re sur­pris­ing­ly vague about what this woman means to you. That you’re exert­ing this degree of effort to seek out pro­fes­sion­al help, even anony­mous­ly, is an obvi­ous sign of your affec­tion. Look beyond gen­der (past and present) and focus on the per­son; rec­og­nize what works and what it is that you’re work­ing tire­less­ly (though mis­guid­ed­ly) to pre­serve. I can’t help but think that your fear is root­ed not in sex­u­al­i­ty but vul­ner­a­bil­i­ty. You don’t feel equal to her; instead of over­com­ing your inse­cu­ri­ties, you’re tempt­ed to cut and run before she real­izes and saves you the trou­ble. While I’m sym­pa­thet­ic to your con­cerns, I’m dis­ap­point­ed by your cowardice.

Neither I nor any­one else can guar­an­tee the via­bil­i­ty of this rela­tion­ship; but I can promise that if you don’t con­front these fears now, you will find your­self back in this sad, lone­ly cor­ner every time you meet a poten­tial mate.

I wish for you the courage to turn off the lights.


Dr. Ted Berry
Berry Picking

Dear Just Asking:

If I were your girl­friend, I, too would be pret­ty teed off if you kept insist­ing to meet one of my exes. I know, you say she’s not your girl­friend. Ten times in your let­ter you reit­er­ate that very point. Sorry to be cute, but Me thinks the lady’s boyfriend doth protest too much. You go on dates, you have sex, you’re meet­ing her par­ents this week­end. And no, I don’t believe that you’re only dri­ving upstate for her father’s 65th birth­day because it’s a great oppor­tu­ni­ty for recon­nais­sance. No one believes that.

What are you after, her ref­er­ences? Those men are her exes for a rea­son. Keep it up, and you’ll quick­ly find your­self induct­ed into the club.


Chatty Kathie

Yo Mall-less Wonder:

Maybe you didn’t real­ize that my blog is about rap (Hence the name, Rapping with Z). But you seem in a bad way, so best I start by drop­ping some truth on you: Most men pray to God that their girls don’t drag them shop­ping and load them down like pack mules. Now you’re try­ing to play it like, because you’re girl doesn’t suck the blood out your week­ends she might have been a man? Come on now; there’s no way you wouldn’t be able to tell. Her voice, her build. Have you felt her claves? You can’t fake that, yo.

I get your point: your girl’s not girly. Add that to her being mum about her past, I see why you got your fin­ger over the Panic Buttons. But seri­ous­ly, who cares what and who she used to be doing? Think of it like this, her life only start­ed when she met you. Maybe she’s hot off a nasty breakup. Maybe she had a bad habit (fill in the blank). Maybe she’s on the lam. Whatever it is, secrets aren’t so bad. They’re like spices; they bring out the fla­vor. Feel me?

See, it sounds to me like your pride’s tak­en a hit. Can’t be easy to see your girl rul­ing your Fantasy Football League (sor­ry Mr. Commissioner, but any­one who picks Eli Manning over Peyton deserves to suf­fer through Monday morn­ing), or that she’s bat­ting at the top of order on your soft­ball team. Don’t take it per­son­al­ly. In the words of the late DJ Tone Def, Be chal­lenged, not threatened.

That said, if you real­ly believe your girl used to know her way around a uri­nal, man I don’t know how you keep hit­ting that. I’m not say­ing it makes you gay.

But I’m not say­ing it doesn’t.

Play on Player.


Z Rodeo
Rapping with Z

Dear Proceeding with Caution:

No, I don’t think your girl­friend is out to usurp you as a father. You should be thrilled that your daugh­ter has tak­en so well to the new woman in your life. Partners who enter our lives soon after a divorce often have dif­fi­cul­ty gain­ing the child’s accep­tance. That your girl­friend is fine-tun­ing your daughter’s foul shot and help­ing pol­ish her three-point turn skills is the ide­al sce­nario. To view it as a threat to your mas­culin­i­ty is pet­ty and short­sight­ed. Their com­fort with one anoth­er demon­strates a lev­el of trust and com­mu­ni­ca­tion which, quite hon­est­ly, you seem to lack. In all like­li­hood, your daugh­ter is expe­ri­enc­ing a great deal of uncer­tain­ty in the wake of your divorce. She’s seek­ing a friend—a sense of stability—just as you are.

Have you con­sid­ered if your dis­tress is not cen­tered on you role as a father but on your plans to move in with your girl­friend? No one will deny that it’s a seri­ous under­tak­ing, and, cer­tain­ly, a healthy anx­i­ety is war­rant­ed. While cohab­i­ta­tion can enhance a rela­tion­ship, it is also an oppor­tu­ni­ty to see each oth­er ‘warts-and-all’. My con­cern is that you ini­ti­at­ed liv­ing togeth­er because you’re in search of her warts. You say that you feel she’s keep­ing some­thing from you. You should not move in with some­one because you think it’s con­ducive to snoop­ing. Curiosity is healthy, sus­pi­cion is not. Do you even know what you’re look­ing for?

All the Best,

Alvin Hipton
Shooting from the Hip

Dear Locked in Pandora’s Box:

Let me be among the first to con­grat­u­late you on your engage­ment. It sounds like you’ve rein­vent­ed your­self over the last year. New home, new job, a reestab­lished rela­tion­ship with your daugh­ter, and, of course, a new woman to whom it seems you owe much of your happiness.

To answer your ques­tion, no, you’re not crazy. That you feel trapped isn’t cause for shame. It’s not even unex­pect­ed. Your life, in some ways, must feel sur­re­al, like the bot­tom might fall out at any sec­ond. To reemerge from epic lows the likes of which you’ve described can accom­pa­ny as much hes­i­ta­tion as ecsta­sy. You won­der, Is this real? How long will it last? What if I lose every­thing again?

I have no doubt that you still remem­ber the pain of your failed mar­riage. The sting of your lay­off. And all the time away from you daugh­ter, the thought alone I find tor­tur­ous. But trust me when I tell you that you are not attempt­ing any­thing that mil­lions of peo­ple before you haven’t suc­cess­ful­ly under­tak­en. You want to love again, and to believe whole­heart­ed­ly this love will endure.

Take com­fort in the knowl­edge that many men and women have tread­ed this land, pro­vid­ing you a clear path through which to find your way. You are not Magellan. You are not Columbus. You are not Lewis or Clarke. You have set out to stick your flag in fer­tile soil known to many. Steel your­self to this task.

You must oper­ate every day with the belief that your life will endure. Your love for your fiancé, your love for your daugh­ter, your love for your­self, and, above all, your love for the Lord. Some days will present more evi­dence than oth­ers, but do not loose faith in your commitment.

I wish you and your fiancé noth­ing but hap­pi­ness as you embark upon this new journey.

Good luck and God Bless,

Rev. Hollis Mitchell
Between You and Him