Great Expectations

A nod to Charles Dickens… just as Pip had to discover his world, the world of dating isn’t as elusive as you might think. Here are some tips to assist your best dating-foot ends up in front, and not in your mouth.

EXPECTATIONS: My ‘five-date rule’ (that I don’t always follow, but should…)

1st date
Anxiety. Fear. Excitement.  There are always many expectations for a first date… regardless if they’re built up from pen-palling it or if only a digit-exchange occurred.

What do I want her to be like? Do I really think he has the attributes I’m looking for? Will he live up to my challenge? Could she be the right one, or just for right now?

Although it’s hard to downplay the anxiety, the platitude “just be you” is really the only way to go. But, remember, as Fanny Brice once said, “Let the world know you as you are, not as you think you should be, because sooner or later, if you are posing, you will forget the pose, and then where are you?” It’s easier to be up front and realistic about your personality and character, then try to continue the lies… especially if the date works out well.

2nd date
Stakes are raised.

-Scenario A- The date was mildly bad to technically horrible. This second date is only to give the person a fair chance in the sense that rushing a decision never helped anyone. What if he was nervous? What if the redeeming qualities will outweigh her awkwardness? Is he worth a second look?

-Scenario B- The date was fairly decent to utterly amazing. This second date will prove if this person can keep up the charade of being perfect. What if I exhausted their library of good lines and cute tricks? What if he makes all the girls feel this way? Is she real?

3rd date
Expectations are slightly relaxed on this day or evening. It’s becoming more relaxed… yet some of the bigger questions about past relationships (remember to not bash your ex! Speak frankly and objectively, as much as possible) and goals for the future are being sussed out. Here’s where I trip up: I’m comfortable with this person and we have a lot in common, so we must be a good match! Continue keeping it casual, as much as you are able to.

4th and 5th date
Expectations aren’t as high, but differences become more apparent as the freshness wears off and the  day-to-day routines begin to pervade conversations. Don’t get me wrong, it’s unbelievably nice to have someone to talk about work that day and the listener knows exactly the players of the story, but don’t confuse “how was your day at school, kid?” with retelling a tale to show how you react in certain situations. The potential boy- or girl-friend still doesn’t know you completely. Past accounts or daily reports may bring up heavier topics that you want to be prepared with answers for… a frivolous example:

The same week I got my driver’s license, my dad bought me a car…” brings to light how spoiled I am. I sure as hell hope I don’t act it, but can that be seen in only a few encounters?

Now, let’s talk about sex, baby
There’s no right or wrong answer, here.  Whether or not you agree with it, my dears, there is a double standard for women regarding the ease of progression into an intimate relationship. All involved, be patient… the cliché of ‘when the time is right,’ comes to mind. Pushing for sex is neither classy, nor a turn-on. Whether it’s the first date, the thirtieth, the wedding night, or somewhere in between, some conditions are mandatory:

  • Exclusivity. (If you’re not a monogamist, this doesn’t apply to your kind.) If you’re in the game for keeps-and for health reasons- it seems very important to know (not guess, assume, or be in denial about) that you are the only one having sex with this potential partner.
  • Laughter. I know just about everyone says they’re looking for someone with a “good sense of humor,” but that can mean so many different things. Humor taste varies incredibly, but what doesn’t is the ability to laugh during your sexy times. As little known Hermione Gingold once cautioned, “Really, sex and laughter do go very well together, and I wondered – and I still do – which is more important.”
  • Intimacy. Being naked isn’t the foundational requirement of being intimate. Setting isn’t necessarily important, just the personality and desire to honestly share mentally, physically, emotionally, and spiritually with your partner.
  • Inspiration. Is the kissing game just not enough? Be in the moment and feel the excitement of gradual physical closeness and of foreplay. No need to rush things if you haven’t a timeline.
  • Trust and Security. Do you feel ready, without a doubt, to be naked with this person? Baring your soul is less scary than baring your entire body; lights on or lights off, you’ll still be out in the open.

**Caution to first-date jumpers and those, term-lacking, who go home with someone else from the bar… can you actually trust this person? I’ve heard horror stories of women being taped by the ‘nice-boy’ at the bar and in contrast, lovely stories of couples who have been married a number of years after that unexpected night of passion.**

And, the BIG question…
I often get asked a panicky, “Where do we go for the first date?!”
I am a huge fan of first dates being in a coffee-shop.

  1. If someone arrives early and orders before the other gets there, that sets a precedent.
  2. If the date is going badly, once the drink is finished, you may leave post-haste.
  3. If the date is going well, you may either get another drink, a food item, or continue the date elsewhere (I suggest going for a walk by the lake or around the well-populated, surrounding neighborhood).
  4. It’s easy to feel comfortable in a café with other people around, things that can distract you if necessary, a nearby bathroom to text the waiting cavalry (see a blog on exit strategies later), etc.

Need more date-night tips (and the reasons behind choosing what particular food option or setting) for your first through eleventh date? Read a very thorough guide here and you won’t regret the new knowledge!


Is your barista really flirting with you?

We all get sucked in… that pretty barista flashing her smile behind the counter at your favorite cafe… the smokin’ hot waiter you see every girl’s night out. We’ve also all (well, most of us clever folk, anyway) been warned by The Onion in “Sources: Barista Not Actually Flirting With You”.

However, do not lose hope! It is still possible to score a date with this incredible cutie.

Let’s review… yesterday, a man came into the independent cafe I work at in morning, places his order, and we exchange pleasantries (“You’re new?” “Yes, I love working here.”) He then comes in a second time, hours later for an iced coffee refill. He continues our conversation about Chicago and talks about where he lives, his job, and asks me about my life. By now, he’s casually called me cute a couple of times–with no acknowledgement verbally from me–and before leaving, takes the plunge: “I don’t normally do this, but would you like to grab a drink some time?”
I hesitate.
“You’re seeing someone?”
“I am. But I am flattered that you asked.”
He says, cordially, “Lucky guy! Well, I’ll be around… maybe if you and he don’t…”

What he did right:
-Tried to get to know me.

What he did wrong:
-Too fast, too soon. It would have been easy for him to deduce that I wasn’t single if he had another couple of face-to-face encounters. Little effort over a couple of weeks goes a long way.

A few things, pulled from actual customer-initiated conversations, not to say while you’re trying to spit game. (yes, I had to google that.)

  • (talking about a dead battery in his car) “I just need some juice… guess I’ll have to use my tongue!
  • “Camping at the Apostle Islands was amazing… next time, you should go with me.”
  • “Have you ever thought of doing something more with your life? Retail is such a dead end.”

Some things that do fly…

  • “My ex girlfriend and I-you know we were dating quite awhile-went rock climbing out there a lot.” (this shows that you were in a relationship, but are now single AND that you aren’t embittered from it.)
  • Non-invasive questions about the person, that can be taken as casual conversation with open-ended answers. For example, “How long have you been a server? Do you like it?” or “What made you move to Chicago?”

I’d had some fairly great dates with customers… and some, well, not so grand ones. The mystery is part of the dating game! Both of the customer-crush-turned-dating-for-around-two-months started similarly. Take the Boston Marathoner: I was still working at the Lincoln Park cafe, inside a bookstore, and his third time in the store I had no other customers to attend to. In talking about politics and Obama (as all everyone in Chicago did fall 2008), he offered to send me a link to an intriguing article. It was nice that he left it open and I wrote down my gmail. It wasn’t two days later when we had our very own coffee date set up. The next year, the same sort of thing, working at a Chicago based tea cafe in the loop. I’d been helping my customer-crush a few months… always a smile available for that gorgeous brunette with his eyebrow ring. He came in just after the early morning rush of the Suits one day and we had a few moments to talk about our Halloween costumes; him showing off pics from his iPhone and, because I was working and had none on me, gave my facebook link up to show off my own festive costume. (Facebook usually is a pretty good indicator of relationship status, though it can be very private, so don’t ask! Just leave it as an option.)

So… your tips, in case Cupid forgets to show up:

1. Be loyal. Come in multiple times when he or she is working. Ideally, get to know their first name and some hard facts before attempting to move it out of the cafe.

2. Tip. It doesn’t have to be a lot, but people in the service industry know how much this matters. And people not in service? You should know better at your age!

3. Pay Attention! Does she talk to everyone in the same, over-friendly way? Does he lean in, casually brush your hand at opportune moments? It wouldn’t hurt to start practicing your own verbal and physical cues, too.

4. Motivate. Think: What’s the worst that could happen? She says she’s taken… He says I’m not looking right now? What’s the best? Good conversation, dinner or coffee with a new and fascinating person, casual sex, an exciting activity partner, or an amazing relationship (platonic or romantic)?

Now, go get ’em tiger!