LOVEDATING: TRYING NOT TO BE TOO CAUTIOUS WITH DATING

I’m sure you already know this but there are a lot of bitter single people in this city. After so many dating games and dating misadventures, some people tend to become cynical. What’s really ironic is when you are lucky enough to meet someone who won’t run game and act shady, what happens? Some people question it! A guy calls when he says he will, and she wonders if he is too eager. I man wants to do special things for a woman and suddenly she gets tagged as desperate. I know we all have some battle scars, but how do we stop being so bitter and cynical about it? How do you know when to take a risk on someone and still be cautious?

How do we stop being so bitter and cynical about it? – you have to attempt to release bitter after each and every incident that might cause you to be bitter. you hear it time and again, take time to get right with yourself after a breakup before you put all those damaged goods back on the market. personally – I don’t take issue with being cynical. being cynical, to me, is like paying attention to your gut instincts. being cynical might save you a lot of drama. sure, you might miss out on something good but more likely than not you’ll avoid something bad.

What do you do to stay optimistic and hopeful? – I’m definitely more of a pessimist than an optimist. i don’t do anything in particular to stay optimistic and hopeful. I simply take each individual person and each individual circumstance for what it is. I resist allowing myself to be lonely enough or bored enough or desperate enough to settle. all I can do is get all cliché and think “good things come to those who wait”, “god time, not people time”, “if it’s for you, you’ll have it”. blah blah blah. in a nutshell – don’t sweat it.

How do you know when to take a risk on someone and still be cautious? – I am not much of a risk taker. you either meet eligibility criteria or you don’t. that’s not saying there’s not a wee bit of wiggle room but I’m certainly not trying to rehab someone.


I refer to people who engage in that as contrarian cynics. No matter what you do, no matter how appropriate, harmless, thoughtful, or considerate your actions are, they will be met by second-guessing and sideways looks with an assumed ulterior motive. You have to prove your trustworthiness to people to gain their confidence but when proving yourself becomes a perpetual obstacle course with no finish line or progress attained, it’s time to move on. They have a total lack of distrust in people and it’s easier for them to not trust than to learn to let someone earn their trust because they rely on the law of averages for someone to fail them in their minds to justify their stance.


When I was dating I constantly ran into the phenomenon of starting out behind the eight ball. A large percentage of the time, it began with having to work overtime to prove that I wasn’t the other guys they had encountered in the past, at which point the real dating could begin (if it got that far).

I can’t tell you how many times I moved on because I felt like I was running the gauntlet and having to dispel the fact that I was going to do the same things others did rather than being evaluated at face value…

Cynicism is not wisdom. Cynicism masquerades as wisdom, but cynicism is a self-imposed blindness. You put the blinders on yourself to protect yourself from a world that you think might hurt you or disappoint you. Be a fool. Believe things will be good. Better to be hurt.

Cynicism is defined as an attitude of scornful or jaded negativity, especially a general distrust of the integrity or professed motives of others.

People become cynical after being used or abused by others. People become cynical when life kicks them around. They end up not trusting anyone for fear of another disappointment or heartache.

If you take that kind of attitude into a relationship, you won’t get far. Most emotionally healthy people are not drawn to cynical people. It’s pretty easy to spot someone who is hopelessly negative all the time. All you have to do is listen to them talk. Everyone is out to screw them…everyone is dishonest…everyone is evil.

I can understand that a cynic is trying to protect his heart from painful experiences. But a person with a closed-off heart and mind will have a tough time giving of himself to another person. Intimacy is nearly impossible since you don’t trust anyone not to hurt you. That can get lonely after a while….which will likely make you even more cynical.

Emotionally healthy men are not drawn to cynical women. A cynic cannot be a Great Lover. Be a Great Lover.