Dating – horror or otherwise

Being ballsy can pay off

I like to preach that taking chances – especially in the dating arena – is generally a good thing.

That said, I’m terrible at taking my own advice. I’m very timid when it comes to dating and doing things that could potentially get me dates. The few times I’ve done ballsy things in the pursuit of a date, it hasn’t really resulted in much.

But it can, as I’ve recently found out, pay off.

On Sept. 6, I found myself (as I have so many times in the past) at the Abbey Pub for the monthly free Tossers show the first Friday of the month. I was by myself, enjoying some Irish music and several glasses of Jameson on the rocks.

The waitress who made sure my Jameson glass remained full was very sweet and looked like someone who would be right up my alley. Great smile, tattoos, calm and easygoing demeanor.

The show ended and I was full of whiskey, though not sloppy. I told the waitress I’d like to close my tab. She brings me my receipt to sign and I do. But I do more than that. I write my name and phone number on the back of the customer copy, along with a note asking her to give me a call if she ever wanted to have a drink with me. In my world, that’s pretty ballsy. I blame the whiskey.

Some time goes by and I don’t hear anything from her. I’m not really surprised. She was a young, attractive waitress who probably got hundreds of phone numbers from customers and probably didn’t respond to any of them. So I put it out of my mind.

Fast forward to Nov. 1. Again I’m at the Abbey to see the Tossers. I sit down at a table and she’s there. She comes up to me and says hi very excitedly. We exchange greetings and then she surprises me. She said she’s glad I came because she lost my phone number after that last show. So I get a napkin and write it down again for her (yes, I know the phone-number-on-napkin thing is kind of trite, but I also think it’s kind of cute) and tell her I’d like to have a drink with her. She says she’d like that.

The end result is that we’re going out this week. Wednesday, in fact, as it’s her night off.

I’ve had a spell of bad dating luck of late, so this was nice. Hell, it may only be one date. But the mere fact that she cared enough that she lost my number to ask me for it again was a huge confidence boost.

The long and the short is that I’m glad I finally took my own advice and took a chance. Even if this lady and I only hang out once, it’s worth it.

Categories: Dating - horror or otherwise | Tags: , , , , | Leave a comment

A question for the ladies

Ladies, do those of you that do online dating ever send an unsolicited message to a man in whom you think you might be interested? And to those ladies who do not take part in online dating, do you ever initiate conversation with a guy in a bar/grocery store/coffee shop/etc.?

Here’s why I ask. It’s no secret I use the dating website OkCupid and I’ve used others as well. My relationship with OkCupid is the longest I’ve had with any dating website, though over the course of the four years I’ve used it, I’ve definitely deactivated my account and reactivated it months later a couple times. But I digress.

Anyway, in my years using OkCupid, I’ve noticed that while I’ve traded many messages with many people, the vast majority of those exchanges were initiated by me. Oh sure, I’ve had people rate my profile highly, but I’m talking about actual exchanges of messages. The vast majority of the message exchanges in which I have taken part have been initiated by me. And in talking with straight, male friends who use OkCupid, the same is true for them.

And that’s kind of frustrating. First off, sending someone an introductory message is tough. It’s never easy to figure out what to put in one. They’re like cover letters for resumes. You have to customize each one because you don’t want to be the guy who copies and pastes messages from one girl to the next. That’s a lot of pressure.

Additionally, waiting for the guy to make the first move seems counter-productive, especially if you’re on a dating website. I tend to send messages to people who I know  have visited my profile two or three times because that usually means they gave it more than a cursory glance and found something in it they liked or we had in common. And when I send those introductory messages, often I’ll get this sort of thing in their response: “I noticed [insert profile details here] when I was looking at your profile the other day and am so glad you got in touch!”

But that begs this question: Why did you wait for me to get in touch instead of sending a message yourself? If I find myself visiting a lady’s profile more than two or three times, I’ll send her a message because she’s gotten my attention. And yet for the most part, even women who have visited my profile several times seem very hesitant to send that first message.

And so, ladies, here is what I would like to know from you:

  1. Do you send unsolicited/introductory messages via dating websites?
  2. If not, why not?
  3. How can a guy increase the likelihood of you sending them an unsolicited message? Or do you just have a blanket rule that you will never send one?

Thanks, all. I’m not trying to call anyone out here. I’m genuinely curious and would love to read your comments.


UPDATE: My Twitter pal Nycole, who blogs over at Secret Lives of Chicago Singles and her own blog, the Savvy Brunette, commented on this post with a link to something she wrote about this very same topic. It doesn’t answer the question of WHY ladies often don’t make the first move (though it does ask it), but it definitely takes them to task for not making it. Click here to read it. Seriously. Read it.

UPDATE 2: Also, just for the record, I know that no real evidence exists to prove my correlation between repeated views of my profile and actual interest in me as a potential dating partner. That said, I think the idea makes a lot of sense and I can’t think of any better way to even theoretically gauge interest in me as a dating partner. So I’m going with it until some scientist comes up with a better method to gauge how interested the female population of OkCupid is in me. Any scientists reading this … make that happen!

Categories: Dating - horror or otherwise | Tags: , , , , | 4 Comments

No guts, no glory … and why honesty is *ALWAYS* the best policy

A while back, I went on a date with a lady. It was nothing terribly unorthodox. Just coffee.

But that first date turned into a second, which turned into a third and so on. Before I knew it, we were getting together two or three times a week and planning two and three dates ahead. Things were going well. It appeared to be on the verge of turning into a *GASP* relationship.

That nebulous phase between casually dating and full-blown relationship is hard to navigate. There’s usually no clear line separating the casual from the formal. Such was the case here. But, being the guy I am, I wanted to know. I wanted to know where that line was and had we crossed it or were we on the way toward crossing it. But most importantly, because I knew what I thought about the situation, I wanted to know if she was thinking similarly.

The problem is that the only way to find that out is by asking. And asking such questions can either be a great idea or a terrible idea. And you never know which it’s going to be.

Nonetheless, I’ve come to the conclusion that with dating, sometimes you just have to bite the bullet. After spending a couple days trying to work up the courage, I finally decided I had to ask. With “No guts, no glory” being repeated over and over in my head, I asked if we were kind of thinking similarly about the direction the relationship was going. I told her I was in no rush to put a label on things, but rather just wanted to know if our brains were working the same.

And she said no. She wanted to keep things uber-casual and I was thinking the thing was drifting toward the formal. She was just not interested.

And then she did something weird. She apologized. I asked her why she was apologizing. She said it’s because she really liked me but not in a relationshippy way and she knows it sucks that I was thinking it was headed in that relationshippy direction and she didn’t want to upset me and blah blah blah freakin’ blah.

I told her she had nothing to apologize for. She was honest. And that’s all I could ask for. She didn’t try to string me along. She didn’t ever suggest that she might be more interested in me than she was. She told the truth.

Honesty, especially when it comes to figuring out the dynamics of your own relationship with someone else, is always the best policy. Too often when people start to date, they worry too much about upsetting the other … to the point that it becomes very hard to break it off because you’re deathly scared to tell the other person you’re not into them.

And that, folks, is ridiculous. You may not always like the truth, especially when it comes to figuring out if you and your new Friday Night Date Buddy are on your way toward full-blown boyfriend/girlfriend status. As in my case, I didn’t like the truth. But I’m glad I know it. If she’d just kept me thinking things were moving in a more formal direction from casual dating, it would have wasted a whole helluva lot of time. This way, we can both make a super-clean break and move on.

Categories: Dating - horror or otherwise | Tags: , , , | Leave a comment

What do you want to do?

At first blush, the question “What do you want to do” seems very simple.

But as anyone who has ever asked anyone else out on a date will tell you, it’s not so simple. In fact, I’d wager that question is one of the most agonized-over of all the questions dating people will ask each other.

I exchanged this set of text messages with a lady I’ve been on a few dates with. The context: We had made plans to get together, but had not decided on anything beyond “We’re getting together Thursday.”

Me: So what would you like to do tomorrow?

Her: Well.

Me: Well?

Her: Do we need to do anything? Or, maybe to rephrase, what would you like to do?

Me: No. We do not need to do anything. I am more than happy with a lazy night in.

And that’s why the “What do you want to do” question causes so much consternation. It’s the assumption the lady pointed out so eloquently. Asking that question in that way assumes that you want to do *SOMETHING* as opposed to nothing. And doing nothing can be a wonderful thing.

When two people go on their first few dates, they often don’t know each other well and may be trying to impress one another. One of the ways we try to impress people we’re dating is by showing them we are interesting people who can be more creative than the old standby drinks/coffee date. We tend to forget that a lot of those really unorthodox/creative dates are not terribly conducive to getting to know someone.

I wrote a while back about how I need to stop taking dates to see the Tossers play their monthly free acoustic show at the Abbey Pub because inevitably it will be the last date. I think, upon a bit of reflection, that the reason it was always the last date is because we didn’t know each other well enough to get beyond a date where it’s hard to talk or concentrate on anything beyond the music and your drink.

Think about it: When you start dating someone, each date needs to be a progression from the last. You learn a little something more about the person. You develop a little more trust in that person and they develop a little more trust in you. The conversation evolves from small talk into real talk.

BUT! When you’re at a live music event – even an acoustic one – it’s difficult to converse or do anything besides listen and occasionally order another drink. You sure as hell aren’t going to learn much about your date. How can you? You can’t even hear each other across a table.

And I think that’s why every date I took to see the Tossers was the last date with that person. Without conversation, the date didn’t progress from the last bringing the relationship (such as it was) to a dead stop. It’s not that the date was such a bad idea. It’s that in order to make a date like that work, you have to be at a point with someone that you don’t need conversation to move the relationship forward.

That’s what makes the “doing nothing” date perfect for folks who are just getting to know each other. That’s what makes the coffee/drink/takeout-on-the-couch dates so brilliant. Without the thing-we-are-supposed-to-be-doing hanging over your head, you’re free to talk, laugh and get to know each other.

So embrace the idea of doing nothing as a date. You never know. Something good might come of it.


Categories: Dating - horror or otherwise | Leave a comment

Secret Lives of Chicago Singles

Hi, folks.

You all know I like talking about dating adventures. Well, I’m hardly the only one.

That’s why I’d like to suggest you guys check out Secret Lives of Chicago Singles. It’s in its infancy at the moment, but I suspect it’s going to be pretty cool. The backstory is that the 9 contributors met via the InterWebs and discovered a shared frustration with Chicago’s dating scene (it’s a damn frustrating scene, to be sure). And like any normal young people these days, they decided that the best therapy would be to blog about it.

So go ahead and click on over to Secret Lives of Chicago Singles. There’s a link in the second paragraph of this post and I put a link under “Blogs I like” on the left side of the page.


Categories: Cool links, Dating - horror or otherwise | Tags: , , , , | 2 Comments

Learning from our mistakes

George Santayana wrote in The Life of Reason that “Those who cannot remember the past are condemned to repeat it.”

That, apparently, is a lesson I need to learn, at least when it comes to dating. I’ll explain.

Last Friday, as I have so many times before. I went to the Abbey Pub. I was there for the same reason I’d been there many times before: It was the first Friday of the month and members of The Tossers (the band whose song “Where the Beer and Whiskey Flow” I stole for the title of this blog) were playing their monthly, free “First Friday” show. It’s an unplugged show and it’s always a wild time.

And this particular Friday, I had a date with me. It was someone I’d been out with a couple times before. But that night was our last date.

I was sort of surprised, but looking back, I realize I shouldn’t have been.

You see, I go to the Tossers’ “First Friday” shows pretty much every month and I’ve taken several dates there when I haven’t gone by myself. And without fail, every time I take a date there, it’s the last date I have with that person. And last Friday was no exception.

It doesn’t matter how many dates I’ve been on with someone. If they come with me to see the Tossers on the first Friday of the month at the Abbey Pub, it will be the last date. I’m not sure why.

And yet, even after this happened a couple times, I continued to bring dates there. And every time, like clockwork, it was the last date. If it was a first date, there was no second. If it was a third date, there was no fourth. And so on and so forth.

So I think the time has come to break the pattern. I’ve already invited a buddy of mine to next month’s first Friday show and he’s down for it. But even if something comes up and he can’t make it, I’ll go either by myself or with another friend. I will not bring a date.

Categories: Dating - horror or otherwise | Tags: , , , , , | 1 Comment

Welcome and sláinte

Welcome one and all to Where the Beer and Whiskey Flow.

This blog has been on hiatus for about a year, but I decided I really needed to start blogging again. The bug never really went away, I guess. But you’re not here for a history lesson. If you want to know a bit about this blog’s history, feel free to check out the “About the blog” page.

I’ll kick off this party with a story.

My buddy David and I were at Sheffield’s over the weekend. Great beer list, by the way. We had a couple beers and made some new friends. Around 1 a.m., we decided to find another spot to end the night. So I bellied up to the bar to close out my tab. As I waited for the bartender, I planted my butt on a stool.

A lady sat down next to me. She was pretty attractive. I smiled at her. She smiled back. I said hi. She said hi. And then things got weird. She asked me if I would be down for a threesome. Until that point, there had been no mention of a ménage à trois. There had been no words out of either of our mouths besides “hi.” But here she was, asking me if I wanted to have sex with her and another guy. She didn’t even know my name.

I politely declined the offer. She asked if I was sure; I said I was. She wished me a good night and walked into the arms of some guy.

So that was my weekend. How was yours?



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