The Bitter Single Guy’s Relationship Advice

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~

Another Ice Cream Saturday Night

Saturday night and the ice cream is flowing…

Dear Bitter Single Guy: It’s a Saturday night and pitifully I have stumbled onto your website after vowing to stay in my pj’s and to end all attempts at contact with the opposite sex forevermore.  Wish I had a good recent story of a breakup or crazy codependent shenanigans to share, but instead I write partially out of a sense of boredom and apathy, and partially… no wait… it’s almost totally out of boredom. Sorry. But wait… I just read your little bio that you have a Masters in Psychology, which has upped my interest and made me want to at least try to formulate something worthy of a Masters level psychological type response.

O.k., here is my attempt… I have never been a dater, and have only ever been in one serious long term relationship in my 33 years on this planet.  I have liked guys who didn’t like me, and I have been liked by guys who I thought were moderately psychotic or at least semi-geeky and not my type. Now I have joined an online dating site, simply because I don’t want to be alone for the rest of my existence, but I am finding that this experience is growing old very fast.  I find it exhausting trying to be some perky, chipper wifey type material- and I have interestingly found that a good chunk of the guys that I am supposed to be compatible with stop writing when they hear about my education (yup – Masters as well). And then I get exhausted trying to weed through the profiles of 40 something year olds who still live with their mothers which are frequently sent my way.

So here are my questions… do I give up and live in my pj’s for the rest of my life?  Do I pretend to be an un-intelligent simple girl just so I don’t scare guys off?  Do I just try to come to grips with the fact that if I don’t want to be alone I need to hook up with a mildly psychotic mama’s boy?

I’m going to go find some ice cream.  This is depressing. ~Investing in Ben & Jerry’s~

Dear IBJ: Wow, the Bitter Single Guy is impressed! Take note, teens and twenty-somethings: there is a level of bitterness accessible in your thirties and beyond that you can only imagine now.

Several things IBJ:

• You have to play the game, at least a little, if you expect to win. If you’re not a dater, then it’s going to take longer for you to find a useful relationship than it would for someone who’s in the game.
• The BSG will delicately say that your interpretation of guys bolting when they hear about your education is much more likely to be your baggage than theirs. But if it’s not, then the BSG suggests meeting more guys whose experiences (including education) are more like yours.
• Online dating is not what people want it to be. Don’t sign up for one of these services and then sit back and wait for the offers to roll in. Online dating is a process of you responding to profiles in order to have way more conversations than you want in order to find one that fits.
• Finally, why don’t you find other things to do on a Saturday night? Hang with friends, join a social group, take up music lessons or some such thing. There are all sorts of ways to spend rewarding time (the BSG means NO disrespect to ice cream here) than just going on dates.

Patience, IBJ. Believe it or not, there are some folks for whom relationships come infrequently. Your time will come; do what you can now to be ready when it comes.

~BSG~

First chance at love

Dear Bitter Single Guy: I have incredible standards. I am never attracted to anyone who isn’t a perfect 10. I’m a junior in high school, and I have never had a girlfriend. It’s not that I have no confidence or I’m butt ugly or anything. Normally the girls I like are out of my league. My best friend introduced me to a girl just recently, about a month ago. She wasn’t a super model, but there was an instant attraction to her. She doesn’t treat me like the other girls.

Now, all of my friends know that I am interested in her. I think she may be interested in me. We have a lot of physical contact in school and she makes me walk her to class. It’s hard, though. My best friend, we will call him Fred, is best friends with her. He constantly offers his help, which I don’t always want.  Another thing is, he’s always around when I am with her. Since they are best friends, he’s too much of a distracter and he steals time I want with her. I can’t invite her to just hang out with me one on one, that’s too forward. When we all hangout, the same thing happens. It’s also like, we are really good friends in school. Outside of school, we don’t talk much outside of facebook (yes I know). We have talked on the phone once, she called me. Apparently Fred and her talk on the phone constantly. She isn’t interested in Fred, though. Fred is more of the “best friend” guy, not the boyfriend.

What do you suggest I do? Should I grow some balls and call her? That’s random, what would we talk about? How do I get my relationship deeper with her, while Fred is there? How can I take the spotlight off him? ~Ready for First Base~

Dear RFB: The Bitter Single Guy thinks you know the answer to this already: grow some balls and call her. Clearly, she’s already demonstrated sufficient testicular fortitude to call you, right? If she’s not interested in Fred, but he’s constantly mucking up your time with her, then the BSG thinks it’s likely that Fred is interested in her and is using his powers of annoyance to ruin your chances. Sounds like he’s succeeding, eh RFB?

Call her on the phone and talk to her. Invite her out for an eggnog latte…it’s the season for those, right? Yes, it’s forward and yes it may seem random, but it will send the message that you want to send which is “I’m interested in you.” Annnddd……GO!

By the way RFB, “only interested in those who are a perfect 10″? The BSG promises that approach to love is going to bite you in the ass sometime, so he recommends getting ready.

~BSG~

Almost Had a Date!

Dear Bitter Single Guy: I’m an Indian who studies in USA. Since moving, I have not dated anyone because nobody I liked asked me out and I was busy adjusting to the new environment. Early this year, I went out partying and this white guy asked me to dance. We danced. He invited me out for a late night snack and wanted to take me to his place for a game of beer pong. This scared me since I’m from a different culture so I refused to split from my group to go to his place. I also do not drink. He seemed disappointed but that was the end of it. I gave him my number but he never called. Recently, I saw him on MySpace and added him as a friend but he does not communicate with me even if I’m a web-page away. I have begun to like this guy. What do I do? I would prefer if he made the first move. He is not conservative but I am willing to date a different type of guy. ~Ready To Date~

Dear RTD: The Bitter Single Guy thinks this guy was interested in a one-night thing and nothing else. Let him go before you start to look desperate. You’ll send the message that if you’re good enough for a quickie, you’re good enough for a date. Relax, it’ll happen.

~BSG~