The Bitter Single Guy’s Relationship Advice

Getting A Date at 57

Dear Bitter Single Guy: Man, thanks for the great insights, you’ve helped clear up a lot of muck. Well, here is some of mine (others might have a similar problem): I’m a 57 year old man, haven’t dated in 15 years, haven’t had sex in 12 years, and the totality of my relation experience since the age of 21 barely exceeds 3 years (yeah, I figured it up – pretty sad).
I’m physically healthy and attractive, but I tend to be reserved (read shy) in manners and conversation. Outwardly at times I appear to be an extrovert, but then I become self conscious and clam up (passive/aggressive?). I’ve been more of the “dumpee” than the “dumper”, and neither sets very well with me. I tend not to be very assertive or demanding with the women I’ve dated, but it makes me feel I’m being like I’m being too aggressive, and then I become unsure of myself… oh hell, that’s pretty much the short of it. Would therapy really help, or am I hopelessly done? Thanks again. ~Pathetically Bitter Single Guy~

Dear PBSG: The BSG first wants you to know that there is ALWAYS hope, but that’s not to say that you should sit back and wait for something to come to you.
Short answer: yes. Therapy will help. Get someone qualified to help you unpack the reasons for your unsatisfactory (to you) relationship history.
Longer answer: If the BSG were prone to leaping to unsubstantiated conclusions based on mere fragments of information (in fact, he is QUITE prone to this) he would tell you that you’re over thinking the whole messy process. You’re coming out of a generation where many folks found and secured relationships early on and stuck with them. The BSG suspects that most women you meet are divorced and have some trepidation about the fact that you have limited relationship experience. Most folks expect a past committed relationship or two from folks your age. The BSG isn’t being critical, just letting you know that this is likely an expectation among your target population.

Talk with your new therapist about the kind of response you can give to a woman on a date that will not make you seem creepy. Seriously PBSG, don’t wait…call and make the appointment today. The BSG looks forward to getting an update ~BSG~

Feels Like a Coward

Dear Bitter Single Guy: So I’ve known this guy since I was 13 and a half. I am now 17 and a half. They say that love at first sight doesn’t exist and that you don’t know what love is until you’re an adult. He’s been through several girlfriends. And recently this girl Kasey was with him and he almost married her except he recently found out she cheated on him 3 times. His name is Robbie. I didn’t know before but I know now for a fact since I’ve now been through the relationship loop a few times that he does in fact hold an interest for me and he has for a very long time. It feels as if it’s finally my chance to be with him and I have no idea what to do. There’s so much more about the time I’ve known him I probably should say but I really don’t know how I should approach this situation. This is different than any other romantic situation I’ve ever been in because I love him. I always have and always will. ~Feel Like a Coward~

Dear FLC: The Bitter Single Guy finds himself wondering at what age we stop using halves in our ages. The BSG himself prefers measuring his age in fractions of centuries, which makes him feel really young.

FLC, you know what advice the BSG is going to give you here, don’t you? You’ve been in love with this Romeo for 4 years, you’ve had relationships, he’s had relationships, you feel a connection that you’re pretty sure he feels as well. Seriously Girlfriend, there’s nothing to do but take the plunge. Ask him out. Do it. Invite him to a movie, to have coffee, to do something appropriate in public. Yes, it will hurt if he declines, but doesn’t it hurt a little now?

Do it, FLC. Don’t reach the ripe old age of 20 ½ without ever knowing if he was The One.

~BSG~

When Your Soldier Won’t Stand at Attention

Dear Bitter Single Guy: About 5 years ago now I had some surgery to correct a digestive tract issue I had.  Anyway, during the surgery some nerves were damaged and now I have to take medication to achieve an erection.  Even with the pills, it’s not nearly 100%. Probably closer to 40 or 50.

Anyway, my issue and the way I handled it led to my ex wife leaving me.  I have dated since and fallen for two women.  I am currently averaging one a year that I can actually care about.  I date and everything but I don’t let myself get too close, because in the back of my mind I know that they will probably leave me once they get sick of dealing with my health issue.  I’d appreciate any advice you can offer. ~Afraid to Get Close~

Dear AGC: The Bitter Single Guy doesn’t like to pawn off advice to other people, but most of his advice for you is to engage your doctor in solution-finding here. There are lots of folks with physical limitations (and sexual limitations) who manage to cobble together a delightfully happy life and the BSG doesn’t think there is any reason you shouldn’t be one of those people.

So first, talk to your doctor to see what ideas he has.

Second, see if there is a support group for erectile dysfunction in your area.  There are likely to be folks with similar situations who have ideas about how to move past it.

Finally, and because this is more in his realm, the BSG is going to recommend that you claim this truth about yourself in a way that lets you manage it rather than it managing you. What the hell does the BSG mean by that? Well AGC, the BSG is glad you asked. Mostly he means that by date #2, (if we go with the cultural expectation that sometime around date #3 some bedroom shenanigans are possible if not likely) you should have a conversation with your date if you think there’s going to be a third date. Give your date the chance to decide what her response is going to be before the moment of truth rather than just hoping everything works out in that intimate moment that is likely filled with tons of expectations and nervousness anyway.

You’re still in charge AGC, don’t forget that.

~BSG~

Dating When You’re Broke

Dear Bitter Single Guy: Hi, how are you?

I have a dilemma which is I went through a MAJOR financial crisis in 2008 where I lost it all and it’s been damaging my confidence with the opposite sex. I go out with them the 1st time and they have a great time, but I feel that when I tell them “I don’t have a car” they tend to run away. I used to be the kind of guy that all I wanted was to figure out a way to get laid and was attracting those women all the time, but now I would like to settle down. My financial situation is turning around slowly. I do attract the type of women I’m looking for but I know my finances are the only thing that’s affecting my confidence to pursue them long-term.

I’m just confused, hurt, disappointed and optimistic (yes, all at the same time) ~Pockets Are Empty~

Dear PAE: The Bitter Single Guy is just fine, thanks for asking! Also, he has had the unenviable experience of starting over financially a couple of times and he can understand how it’s simultaneously humbling and empowering.

PAE, the BSG thinks you just need to figure out what your worth is in the absence of money and a car (and the other trappings of your former life). The BSG knows that this sounds really easy when he says it in one little sentence, but he also knows that there are people whose quest to figure this out will be interrupted by dying of old age.  Which is to say: yeah, it can take the rest of your life, but why not start now?

The key here is that you don’t indicate that these women you’re meeting are somehow turned off by your new financial status…you seem clear that the hang-up is yours. The BSG thinks this is an excellent place to start redefining the you who has fewer material albatrosses hanging about your neck (the BSG is particularly proud of that metaphor, but isn’t sure what the plural of albatross is.  Albatrosses? Albatrossi?). By the way, the BSG wonders if you’ve explored all the non-revenue-requiring date options in your town? The BSG himself is a fan of outdoor art, picnics at parks, and “free” day at museums (Thursdays in the BSG’s city). With a modicum of creativity, you can wow the most discerning of damsels, PAE.

Here’s a question, though: The BSG wonders if you’re still in pursuit of the women who were formerly impressed (or at least required) material things like cars? If so, the BSG recommends pursuing some artists. To the BSG’s experience, artists are often insightful, intelligent and – due to their commitment to their art – often accustomed to fewer albatrosses. ~BSG~

Epic Failure in Dating

Dear Bitter Single Guy: The short of it is I am a 25 year old college graduate and have only been involved in two serious relationships. I want to date!

The long of it is that it’s not that easy for me to find someone/no one ever seems interested in me. I’ve been told I am an intimidating person. This is a mystery to me as I am a very petite 5’2″ girl.  I have asked friends and their responses vary: if you smile more you’ll be more approachable. You’re just really assertive. You act closed off.

And I have tried to fix each of these “issues” but to no avail.  The ironic thing is that I am the least stuck up person I know and my friends agree.  Some people have admitted that I intimidated them but once they got to know me, I was super chill and really laid back, which I am.  I have no idea how to change my current situation.  It’s really frustrating when ALL my friends get approached/guys want to date them all the time and I just have to pretend that I am ok with hanging out by myself on a Friday night because they’re all on dates. It probably doesn’t help that I am not a hook-up type person. Drinking and having make-out sessions aren’t my thing.  I’m in such a rut BSG. Any advice? ~Quite A Catch~

Dear QAC: The Bitter Single Guy knows the frustration of being told he’s intimidating. Whenever he has heard that his lack of dating success is due to being intimidating he gets all righteous and loud and verbally demeans his accuser. Sadly, this ruins friendships and seems to strengthen his accuser’s point. The BSG is kidding with you here, QAC (a little).

OK, here’s the scoop.

• You’ve had two serious relationships and you’re 25? You’re not behind the curve at all; you’re doing just fine.
• If people tell you you’re intimidating you probably are. Remember however, that this probably means that you know what you want, are intelligently outspoken, and have limited tolerance for bullshit. These are admirable qualities, but can be interpreted as intimidating.
• If you squash your personality to be more “approachable” you’ll end  up in relationships that don’t work for you because the real you will eventually come out.

Here’s the advice for you:

• Like any dating situation, you need to put yourself out there. Why are you staying home on Friday night? Surely there are hangouts where other confident people hang out? Museum openings, poetry readings, stuff like that.
• Become a regular in some community (events often have communities…the BSG’s town (for example) has a strong spoken word poetry community in which the BSG sometimes hangs out). If you’re a regular you’ll get to meet people and expand your pool of available dates who also have similar interests.
• Look for “intimidating” men – which is to say: confident men like you – and hang out with them! Heck, ask one of them out!

In short, QAC you need to approach dating just like anyone approaches dating. Find a community or social situation in which you’re comfortable and in which you have a genuine interest (if you’re there for the beefcake that will become obvious quickly). Be yourself, but if you find yourself making snappish or off-putting comments in conversation, work on being a little more open. Get out there, girl. ~BSG~