Dating: Why is it so hard?

Warning: This is a personal post, and a mini rant on dating in general. This has nothing to do with finance.

Why is dating so tricky?

Is it because they really are tricky, or are we just over analyzing and making it trickier than it should be?

I was thinking about this the other day when I was on the phone with my sister (who is having a hell of a guy “problem” that I think is imagined), and I thanked my lucky stars I found BF and have to look no more.

I was always of the belief that the simplest way was the most honest and direct way for both guys AND girls.

For instance, if a guy says he likes me on Facebook, or friends tell me he likes me, or there’s a like-something chemistry going on but he never followed through with a formal date, time and place with just the two of us, I write him off.

Then predictably, I’d hear: Oh wait! Hey! I liked you. I thought we were going to have something.

Me: When? In this millennium? Or when humans become extinct?
Them: I was taking it slow, trying not to get rejected, didn’t want to push you, bla bla bla (whatever reason they want to make up for lack of direct action)
Me: Sorry. Too little, too late. (I say something along those lines, but not those words exactly.)

I really loathe ambiguity.

I am not talking about being tactful or trying to be respectful, I am talking about not being clear and using simple words strung together in a sentence that can be comprehended by others.


Basically, they’ve been beating around the bush for 2 months.

They’re both to blame, and they only Facebook or Facebook Chat each other.

He doesn’t call her, she doesn’t call him, they only hang out in group situations where he gets jealous if she talks to a guy and vice versa but they aren’t dating.

But nothing. ever. comes. of. it.

She gives him mixed signals when she tells him she’s down for “whatever” but doesn’t clearly state that she wants one-on-one time with him and not in a group. So the guy is probably wondering WTF is going on.

It’s frustrating to have been part of this conversation:

(Note: Yes I am very blunt with her, because she is the type that cannot deal with being coddled because it just encourages her neuroses.)

Sister: But I don’t want to put myself out there!
Me: So you want to stay single then, is that it?
Sister: No, but I want HIM to ask ME.
Me: What kind of stupid mind game is that? You don’t have to formally ask him out if you’re scared.

Just write: Hey, how’s it going, what are your plans for the weekend?
Sister: But I gave him my number and he knows I’m on Facebook, why isn’t he calling or asking me out?
Me: Because you’ve been giving him mixed signals by not affirmatively saying: Yes I’d like to date you one-on-one.

Ask him what he’s doing this weekend.
Sister: *HORRIFIED* NO! I can’t just write and ask him what he’s doing, that’s WAY too direct.
Me: Oh so you want him to mind read then?
Sister: Well NO, but maybe he just doesn’t like me.
Me: He told you that you were very attractive, he was interested in you, that he is TOTALLY INTO you two being together, and you’re telling me that’s not clear enough for you?
Sister: Are you sure? What if he is just saying that because he does it to all the girls? So why hasn’t he asked me out?
Me: Why are you making this so complicated for yourself?

He hasn’t done it because you are BOTH shy and you were giving him mixed signals on whether or not to go ahead and ask you out.
Sister: He just wants to “chill”. He also didn’t take a cab with me that night, what was up with that?
Me: …..a cab? Is that all you’ve got?
Sister: Well maybe it’s because I didn’t sleep with him yet
Me: … oh good. So now the reason is that you’re not the town slut.
Sister: That’s what _____ said. She said if I don’t keep them interested with sex, he’ll lose interest.
Me: …. I cannot believe we are having this exact conversation in this day and age.

Wash. Rinse. Repeat.


I know guys might find this bizarre but girls actually like honesty, directness and tact. Hate the bush beating. HATE.
I usually wrote people like that off as: flaky, not committed, full of baggage, unsure of self and not ready to date.
I don’t want a wishy-washy person to date, I want to know that they can act like an adult and I don’t need to babysit or mother them when it comes to bigger issues if we stay together.

Hinting doesn’t work. “We SHOULD go out to that burrito place” is not the same was “Let’s go out to that burrito place tomorrow.


If you want to just “chill” with me “anytime” and “anywhere”, I call BS.

Ask me on a formal date, next Friday and let’s go to coffee or dinner or whatever, but don’t just leave it so ambiguous and say you want to “chill”. If I wanted to “chill”, I’d call a friend or do it by myself. If I am single, I don’t need another friend to chill with.


Facebooking me, Facebook Chatting me, Messaging me (Blackberry, MSN, iPhone, or other sorts of BS) and any other bloody thing but talking to me in person, or emailing me with a “Hello, I think you’re nice and I’d like to take you out on a date. Are you free this weekend?” makes me roll my eyes.

Whatever happened to the simple channels of calling up a girl and saying: Hey this is Billy from ______. Are you free this weekend to go out on a date with me? Or talking to them in person?

Ambiguity, gone.

Instead, we’re trying to figure out if taking a cab with us rather than taking a cab with his friend, or the way he orders drinks for you, or WHATEVER ELSE we make up in our heads by over analyzing every action someone takes, rather than just being clear and direct.


So he didn’t take a cab with you. Maybe he wanted to share with his friend.

Maybe he wasn’t sure if you wanted to cab with him.

Maybe he just doesn’t have the money but would rather owe his friend than you.

The point is that it’s just a cab ride, and it isn’t like he grabbed a cab with another girl and started making out with her.

Who cares?

It’s a cab ride. It isn’t a “sign” that he hates you.

So he handed you a used ticket from the club. It isn’t a sign that he’s in love with you either.

Stop reading into that crap.

Here are some direct questions you can ask:

  • Do you want to go out this weekend?
  • Are you free tonight for a date/to go out with me?
  • Do you want to go bowling with me?
  • How about a movie together?
  • Want to go grab a coffee together?
  • Do you want to go to dinner some time?

Just ask. It’s just words. It isn’t life or death.

Somebody explain this to dating wishy-washy-ness to me. I just don’t get it.

About the Author

Just a girl trying to find a balance between being a Shopaholic and a Saver. I cleared $60,000 in 18 months earning $65,000 gross/year. Now I am self-employed, and you can read more about my story here, or visit my other blog: The Everyday Minimalist.