The Bitter Single Guy’s Relationship Advice

Heading Down the Wrong Track

Dear Bitter Single Guy: I probably know the answer to this one, but I guess I need a bit of BSG honesty here.

I met this colleague like 4 months ago. He’s been super nice all the way, but I always had the gut feeling he’s gay – mind you, other people think the same – he talks about cute boys, and even told us about a gay dream he had… anyways, we’ve been out many times -sometimes with friends of his and lately on our own. I think I like him, but I was afraid of him being gay or bi, I guess. So this week we went out and he said he likes me, I’m great, etc. So I ask him if he is gay. And he says no. I said I will think about us getting together, since I don’t think having an office affair is such a good idea. Well, next day he was really mad at me about this gay questioning; he says he liked me because he didn’t really know me, he doesn’t like some things about me. I asked what, and he says I always stress out easily and I’m not much into cultural stuff…He also said if I had really trusted him I would have never asked him if he was gay, because he has shared all his life with me, talked about former gf’s and so on…

2 days have passed by and he’s already flirting with a friend of mine, and keeping me informed on his progress! What do you think? For the record, he had a one night stand with another colleague.  I wasn’t completely sure of liking him on the first place, but now I feel quite jealous, and I also wouldn’t like to lose his friendship, we get along very well. ~Confused at work~

Dear CAW: The Bitter Single Guy thinks you should step away from this train wreck. Whether this Fickle Fig is gay or not, he seems to have pretty crappy boundaries where his workplace is concerned. Unless you both work in a restaurant (which, to the BSG’s experience, is chock-full of inappropriate boundaries but that doesn’t seem to prevent them from operating), the BSG recommends not getting involved.

Plus, the BSG has some of the same concerns you do. Per his post earlier in the week (Girlfriend in the Closet), the BSG believes that sexual orientation and attraction are on a continuum, so a mostly hetero guy making the occasional homo comment doesn’t seem completely out of the question in the 21^st Century. However, the BSG thinks that if Fickle Fig actually wants to attract and date you, then he should be smart enough NOT to talk about cute boys and gay dreams. The problem here isn’t gay, bisexual or straight…it’s just tackiness. ~BSG~

Bisexual and Transgendered: Dating Options

Dear Bitter Single Guy:  I actually just ran into your site and I’m hoping for a reply. This could get lengthy, but I’ll make it short as possible.

I’m 20, a college student, bisexual, and oddly enough, transsexual. I’m pre-op, pre-hormones, but I’m a FTM (female to male). However, the trouble is that I hardly pass as a guy, and when I say I’m bisexual, I actually mean that I’m almost gay. I’m open to dating women, and I’ve been attracted before, but I’m more often than not… head-over-heels for some guy.

I’ve only been on one date (the guy was almost three times my age and was too sexual/creepy to begin with) and my longest lasting relationship was two months.

The problem is that, because of my transsexuality, I’m sort of a fetish object and it really annoys me (I want to be liked for who I am, not what I am). I want to be in an openly gay relationship as a man, and I’ve tried nearly everything to find someone. However, I seem always to fall for straight and/or taken guys.

There are people who are interested in me, but they’re either too scared to say anything or I’m not interested in them. One guy, though, is pretty decent, and even though I’m not very interested in him. 

Honestly, I don’t know where to start or what to ask, but… What exactly should I do? When’s the best time to tell someone about my gender situation (before or during)? ~Not Sure of The Rules~

Dear NSTR: The Bitter Single Guy is blessed by having some friends who are trans, so he finds that he’s actually had a chance to think about situations just like yours. That doesn’t really mean he has an easy answer (answers are rarely easy, NSTR).  But here are some ideas.

Much of what you’re describing is true of any relationship regardless of gender and sexuality. Sometimes you’ll be attracted to people who are not attracted to you, and sometimes people will be attracted to you who you’re not attracted to. Honestly, the BSG doesn’t  know how anyone manages to connect sometimes.

One solution to your concern is one the BSG hopes has already occurred to you: spend time in a community of like-minded folks. This is true if you’re a devout Catholic, deeply into Jack Russell Terriers, or if you’re transgendered.  If you’re not already in contact with a group of other transgendered folks who are faced with similar dating conundrums, find them. Granted, the BSG lives in a good-ish sized city, but he’s surprised sometimes that there seems to be a community for everyone. Find yours NSTR.

As far as fetishism goes, the BSG finds that the line between festish and attraction is somewhat vague. If you only date people with brown hair, that’s an attraction, but if you want to spend hours brushing your partner’s hair then it becomes a fetish. The BSG points this out because you should definitely avoid folks (like the creepy one you mention) who fetishize anything about you (gender, weight, hair color, whatever), but know that there are folks who will find themselves exclusively attacted to people like you (in your case: FTM Trans) and you don’t want to write them off as potential dates. They’ll be much easier to date than educating someone new every time.

As far as when to tell a potential date about your gender status, the BSG wants you to think about what you’re asking that potential date. If you don’t broach the subject until an intimate moment (the BSG is blushing), then you give your date mere seconds to figure out how he feels about your revelation.  This is a lot to ask during what is likely already a highly pressured situation. For that reason, the BSG recommends having the conversation sooner rather than later, even though this could mean fewer second dates.

Even as he provides this advice NSTR, the BSG wants to reiterate his point about finding a community. The BSG can pronounce platitudes about the details of dating in the trans community, but the truth is you’ll be best supported by folks whose experience is more like yours.  But he’s still pretty pleased that you felt good about coming to the Bitter Single Guy…where all are welcome.

~BSG~

Bisexual Guy’s Love Triangle

Dear Bitter Single Guy: First off, I’ll give you the background of my situation.  I’m a guy and I was in a monogamous relationship with a girl for a year.  Three months ago, I met this guy online and we went out and hooked up.  I told my girlfriend that I’d hooked up with someone and the stress of our coast to coast relationship had gotten the best of me and she decided it would be ok for us to go back to an open relationship, but then finally broke up with me a month into it.

Well, since then I’ve gotten really close to this guy, even though he’s only 22 and I’m 40.  To put it straight (BSG: pun intended?), he is the greatest guy I’ve ever met and one of the most fulfilling relationships I could ever want.  To be fair, he is incredibly good looking and talented.  And, we both have considerable finances relative to our ages.  It’s only been 3 months, but I’ve never felt this way about another man.  But, we both are honest about our other relationships and we’re both dating quite a bit.

Now, to complicate matters, I’ve just met a great girl and we went out on a date and kissed and are going to go see each other again.  I think as long as I’m honest, things will work out the best.  But my question is: do you think a girl in today’s society would ever be in an open relationship with a bisexual guy or is that out of the question? ~Kid in a Candy Store~

Dear KICS: For nearly a decade, the Bitter Single Guy has been dispensing advice to his faithful readers (I know ya’ll…TEN YEARS!) and he finds in the past few years that more people – men and women both – find themselves moving between the genders in their relationships. There are folks who believe that human sexuality exists on a continuum and some folks are all the way over on one side (totally straight or totally gay) and there are some folks who fall somewhere in the middle.

Truly, the BSG doesn’t know exactly what he thinks about this theory, but he has definitely gotten more letters like yours in the past few years, so he’ll let everyone draw their own conclusions from that.

The real gist here KICS has very little to do with your bisexual status and more to do with that hum-drum problem of managing a relationship in the midst of constant temptation. The BSG has seen, and is sure that some of his readers will concur, that we never seem more appetizing than when we already have a date. This is the dating equivalent of Murphy’s Law, maybe?

That aside KICS, let the BSG see if he can summarize your problem.

• You were in a long-distance relationship (with a girl).
• You met a sweet young thing online (a guy) and hooked up.
• Now you find yourself getting close to hook-up-guy, making you think it wasn’t as no-strings-attached as it seemed. (welcome to the club; it rarely is)
• Now, since getting closer to Sweet Young Thing, you’ve met someone ELSE (a girl) and plan to see her again.

Your question (to summarize) is if New Girl will be OK with you dating someone else, specifically a male someone else. Gracious KICS, there is so much to work with here. Here goes:

• Hoping that New Girl is down with you dating someone else seems plausible.
• Hoping that New Girl is down with you dating a guy, seems less plausible.
• Hoping New Girl is down with you dating a hot, young guy seems downright unlikely. (you don’t say, but the BSG is assuming that New Girl is closer to your age.)

You see KICS, there is no way New Girl can think of Sweet Young Thing as anything other than competition for your affection. And vice versa by the way…have you wondered what Sweet Young Thing will think about New Girl?

The BSG is going to make this easy for you. You’re worried because the big issue seems to be your bisexuality but in truth, the BSG thinks the big issue is what to do when you are attracted to more than one person. You can go the route of dating multiple folks, but frankly that gets tiring and more often than not, feelings get hurt. Most folks still buy into the idea that dating is a preamble to some sort of committed relationship, so there is a point where someone is going to get rejected (could be you).

The BSG thinks that if you are going to date multiple folks, you should (as you seem to plan) be honest with the participants. You should also be prepared for one or more of them to NOT be down with the arrangement. But mostly, the BSG thinks you should reduce your stable to just one filly. Whether it be Sweet Young Thing or New Girl, give the relationship a chance to evolve before you start adding difficult obstacles to overcome (like competition from the opposite sex).

KICS, the BSG would also be remiss if he didn’t add something here. At 40, coming out of a long distance relationship and coming into your first dude-on-dude relationship with a hot, talented (the BSG and his readers wonder what sort of talents? Yeah…whatever…the BSG knows you were thinking it) 22 year old, you may have some wild oats to sow in a pre-mid-life-crisis sort of way. The BSG recommends you determine whether this is possible and give yourself time to have fun with Sweet Young Thing if that’s what you need. If you convince yourself that the responsible thing to do is to build something Meaningful with New Girl, the BSG predicts you’ll be shopping online again within 6 months. ~BSG~

Boyfriend is a Hidden Bisexual

Dear Bitter Single Guy: My boyfriend and I have been together for 7 years. For the past year I’ve been having dreams of him being with a man. I’ve told him about the dreams and he would laugh and say “no I’m not gay”. Last month I did what most paranoid girlfriends do and snooped on his computer. I found an email account I didn’t know he had and logged in. I found emails from gay men, some of them very explicit. He even told one guy where he lived (his address).

Of course I was shocked so I confronted him about it and he told me he was just confused and that he knew he was straight now. Every time I bring it up he gets very angry. I need answers and I don’t feel like he’s telling the truth. Would it be wrong of me to put software on his computer that will show me what he’s been doing? I love him but this paranoia is running me crazy! ~Don’t Wanna Share~

Dear DWS: The Bitter Single Guy admits that when he read that you had been having dreams about your boyfriend being with a man, he was ready to poo-poo your paranoia, but it certainly appears to have gone beyond dreaming.

First though, the BSG has to answer your question: Yes. Emphatically yes, it would be wrong of you to put software on his computer that will show you what he’s been up to. Really DWS? You want to be that person? Are you running a prison? Besides, what do you think you’ll learn that you don’t already know?

Here’s the deal, DWS. You suspect your boyfriend is bisexual? The BSG believes you’re correct. What your Baffled Beau is defining as “confusion” is actually bisexuality. The BSG has to say though…this isn’t necessarily a bad thing for him in the larger scheme of things! It means that as his life unfolds, he gets to have rewarding relationships with women AND men!  It’s sad for those of us limited to just the one gender <sigh>.

However DWS, it’s not OK for him to explore this side of himself while he’s in a committed relationship with you. So the issue here is not whether or not he’s attracted to men, but whether he’s going to compromise his committed relationship in order to explore this other side.

The BSG believes that this should be your stance: “I don’t care who you’re attracted to; if you pursue other people for romance or sex you’re cheating on our relationship and that’s not OK”. Sadly DWS, the BSG also believes this is likely to be the end of your relationship. The BSG has watched the Coming-Out-Of-The-Closet process before and the beginnings of it often look like you describe. Doubtless your Baffled Beau wishes he were completely straight, but that ship seems to have sailed.

The BSG recommends being as compassionate for Baffled Beau as you can be as he navigates these new waters, but also recommends that you set a firm boundary about what your commitment means. ~BSG~