A four-year monogamous relationship followed, which also ended amicably with my ex-girlfriend in NYC and me dateless in Dublin for three years, but for one disappointing "Crying Game" type encounter.

I'm back in Southern California now. Four-years dateless and counting. What's going on?

Well for one thing, I fall hard when I fall in love and take a long time to get over a relationship before I'm ready to date again. I seem to be hardwired that way.

Then, I'm picky. I have high standards, don't need a relationship to define myself, and would rather be alone than in an unsatisfying one.

Beyond these things, dating when you're past your late-30's is much more challenging than in college. We "older folks" spend the vast majority of our time in the workplace, where dating is--justifiably--discouraged. Not only that, at my age, most of the "catches" are already "caught." Those who aren't, especially if they identify as straight women, are often happily single. From their perspective, the last thing they want or need is a man to take care of. Not that I'm looking to be taken care of, but many straight men--the demographic I find myself superficially stuck in in San Diego when I'm looking to date women--are looking for a wife. Someone to cook, clean, and emotionally baby them. If I were an older woman who'd already done that for a good portion of my life, being single and hanging out with like-minded women friends would be a much more desirable option.

And let's not forget the pink elephant in the room, the "what you see isn't exactly what you get" issue. Here's an easy way to illustrate it: say I walk into a gay bar frequented by lesbians and gay men in a city like Dublin or San Diego. Dykes who might be interested--most of my FtM buddies in long-term relationships with women are with partners who identify as lesbians--look up, see "a guy," and understandably look away. Gay men, on the other hand, check me out and may think, "Hmmmm, haven't seen him in here before!" In other words, "fresh meat." Only, I'm not, lacking as I do that critical anatomical feature so dear to most gay men. It might be different were I looking for casual sex, but I'm not. What is more, even if I were, it's rare, especially on the bar scene, to find a gay man interested in trying to satisfy someone with, well, my sort of plumbing.

Re-stage the bar scenario in any sort of social setting where people mingle. The dynamics shift, sometimes subtly, sometimes hugely, but the underlying facts remain the same: I'm a man without a dick--an anomaly, and clearly not everyone's cup of tea. Short of wearing a t-shirt screaming that bit of news--hardly a good idea from a personal safety perspective outside the immediate environs of San Francisco's Castro District--the dilemma of when, how and to whom to come out adds a psychological obstacle course to the already daunting task of dating, that it frequently becomes easier to stay home.

Internet dating is just as bad. Most of the major dating sites don't even list a transgender category unless it's a section designed for tranny-chasers looking to hook up casually with "she-males" and "he-shes?" Not to put that activity down, but it's not me.

At the recommendation of a dyke friend, I checked out "TangoWire," only to find that, even in the "Alternative, Lesbian Gay" section, they do not offer "trans" as a gender identity, nor do they allow bisexual men to search the women's profiles. Their help-desk answered my email query on how to do that with, "I am afraid Brynn our site will not meet your needs."

No kidding.

If all this were not enough, there's age. I find I can't relate to most people my own age. FtMs I transitioned with used to speak of a sort of "time-warp," in which we regress to the age we were when we definitively repressed our masculine identities. From there, we proceed through a second puberty and sort of "fast-forward" to eventually approach or reach our biological age. This "out of age" experience is not to be confused with a "mid-life crisis," which some of us also find ourselves facing--sometimes in combination with the "time-warp/age-regression" thing.

Talk about a lot on your plate. There we are, re-learning everything from bathroom etiquette, to humor, to public presentation, to fashion, to hailing a cab, to walking at night--you name it!--feeling like a teenager, while we're forced to hold down a job, trying to cope with our families, and then date?! To confuse matters further, we are frequently mistaken for men decades younger than we actually are. I was carded once and refused a beer because I didn't have my ID on me--and I was 43 years old at the time, with a teen-aged daughter!

Even though I transitioned nearly 15 years ago, I still don't feel like I've caught up to my biological age, though I'm definitely starting to look older. My dad, who's 88, living on his own, golfing every other day and with a "lady friend" who regularly plays tennis and golf, makes me wonder if I'll ever actually "act my age." So I guess it's not surprising that my last two relationships were both with partners much younger than myself. I didn't go looking for that, it just happened because I look, feel, dress, and behave much younger than I am and had more in common with them than with most people my age.

Which brings up another big issue: money. Because most of my employment history and work experience has occurred as a woman and single-parent, I'm under-employed for my level of education, underpaid, and carrying more debt than I like. I wasn't socialized as male, so competition in the workplace bewilders me, ensuring that the financial situation won't change anytime soon. One thing many partners seem to look for in a man, especially as they grow older, is financial security. My ex's family objected to our relationship citing the age-difference and calling us lesbians, but they didn't object to her sister's marriage to a man as many years her senior but who happened to be a multi-millionaire.

No two ways about it, this dating as an FtM thing can certainly be a conundrum. One I suspect I'm not alone in facing. FtM friends who live outside major urban centers with large queer populations--and even some who live in them--complain of difficulties meeting interested people. Likewise, I've known FtM friends who stayed in abusive relationships because the prospect of breaking up terrified them so thoroughly. I know. When we break up, we're all convinced--transgendered and cisgendered alike--that we'll never find another partner. But for FtMs, the fear seems a bit more realistic.

I recently met a woman my age while riding the train to LA. We started talking, and really clicked. After a non-stop conversation both there and back, we got together a few times, hung out, I came out to her and she didn't freak out. I'm not sure if I'm interested like that--I prefer to go slow, become friends first, and see what develops--but the last time we hung out she was talking about her recent rather abysmal dating experiences with older men, and out of the blue while commenting on what a great time she and I always had together and how well we communicated, she offhandedly dismissed the possibility of us ever being romantically involved.

I was caught off guard. I should have just asked what she meant. Why was that never to be a possibility? But self-consciousness kicked in--combined with uncertainty of whether I was sexually attracted to her, or merely attracted to the idea of attraction--so I clammed up. I concluded--perhaps unfairly--that her dismissal was due to the fact that I'm FtM. After all, what else could cause her to so definitively dismiss a romantic possibility after only a handful of meetings, especially right after listing the reasons we were so compatible?

At the time, though, I couldn't bear to hear her utter the words, so I didn't risk it. Maybe I'll bring the topic up with her in the future, just to clarify things...I don't know. I need to sort out my own feelings first, and be prepared to hear that it's because I'm FtM.

In the meantime, what lingers is a longing that the issue was never there to wonder about in the first place. Not that I wish I wasn't trans--I love the insights and life experiences I've had because I've experienced life as both a woman and a man. I like being me. But I also miss those heady early San Francisco days, when being FtM was widely considered to be a cool, sexy, attractive thing to be.