I was recognized the other night (a rarity). A woman came over to my table while I was on a date and complimented me on my book and advice. She told my date, “It must be very refreshing to be out with a guy who never makes a mistake and has all the answers.”
Huh? Experts don’t have all the answers; experts continually search for the answers and share the knowledge they gather on their journey. It’s easiest to see in scientists such as Einstein and Newton–always searching for answers and changing equations and hypotheses as they learned more about science. While it’s true I haven’t made any big mistakes in years, I did make one just within the last month.
In February I met a pretty woman at a friend’s birthday party at a bar. She mentioned she was looking for more competitive volleyball so I got her email and told her I’d let her know when I needed a sub (I play three nights a week and constantly need female subs). I didn’t talk to her much but when I needed a sub two days later, I sent her an email. She subbed but I missed the match because I took a date to the Blackhawks’ game. The scouting report on her (we’ll call her “Sheree”) was that she was good and very personable; I should pick her up full-time when a spot opened. I am always somewhat skeptical of scouting reports because guys will often give a pretty woman rave reviews because they want her on the team so they can hit on her; no doubt Sheree has experienced this and is wary. (From a team captain’s perspective, people dating on a team is a pain in the ass! Fights show up on the court, one refuses to play or set the other or some dumbass thing. Sadly, most people aren’t mature enough to make it work. I always tell guys who ask about a woman, “Remember, if it doesn’t work out, you’re far more replaceable than she.”) I became curious to see her play myself before inviting her to join full-time and invited her to sub a few times a week for like two months straight. Of course, we chatted back and forth a little in our emails–”What are you up to this wknd?” “My father is sick,” “How was your wknd?” and so forth. I threw in some harmless flirting (can’t help myself) and we got to know each other a little. I threw a few invites to get some food during the week her way to help keep in touch but she was always on the road for work. (Of course, I couldn’t very well tell her I wanted her to sub in particular because I wanted to see if she was any good!)
Finally, she was able to sub again and I got to see her play. She was a good player and I don’t think I’ve seen anyone have more fun playing volleyball or met anyone who was easier to get along with on the court. She never got frustrated or irritated. Yup, she would be a great addition to any team. That night I asked her where she lived because I had a feeling she lived in a zone for which I wanted parking passes (in Chicago, many neighborhoods are zoned and you can’t park without the proper parking pass; residents in that hood can get daily parking passes and I live right on the border of two zones, so I like to get daily passes from zone residents so I can park as needed). I also asked for one of her friend’s last name, as I have plenty of “Jen’s” in my cell and needed to start putting in last names to know who the hell was who.
The team hit the bar, where Sheree was just as personable as she was on the court. For the first time, I found myself kind of interested in her; however, I was jabbering with my buddy Mike and didn’t really give it too much thought. As she was taking off, though, I did ask if I could give her a call, just in case. “Sure.”
Now came one of the most hated dilemmas in the dating world for guys–you haven’t talked to someone enough to gauge your level of interest and you don’t feel like you’ve had quite enough conversation to ask her out, even if you did. If you snooze, you lose–suppose you don’t see the woman for another four months and then find out you are interested, only to learn she is now dating someone? (Sheree is pretty and personable; not the kind of woman to stay single for long.) It’s one of the few situations I detest. Also, because I wanted Sheree for future volleyball teams, if I was interested I wanted to ask her out before she joined a team, not after; I didn’t want her to think I put her on the team with ulterior motives in mind. I figured I wouldn’t worry about it. If I didn’t see her over the next few weeks, I’d invite her to a simple dinner on a weeknight or something innocent that popped up. End of story.
As luck had it (or possibly misfortune), I got a voucher for two to a musical (free passes from my editor). I invited Sheree, never stopping to think she might see that as a big date. (I never use a voucher, offered to me all the time, for a first date; it’s tacky! What woman wants to think a guy thinks so little of her that he doesn’t want to spend any money on her for a first date? I only use one for friends or innocent engagements. It never occurred to me that Sheree might not have the same reasoning.)
Sheree declined but thanked me. Suddenly all emails stopped and she didn’t reply to any of my offers to sub. (Until then she had always promptly responded.) Uh oh… Even when I emailed her that a woman we had chatted about who was like a second mother to me died, she didn’t reply. Not so much as an “I’m sorry.” (It actually pissed me off for a little while; that’s pretty cold.) That seemed very out of character for her. I thought about it and realized from her perspective things looked weird. I asked her to sub all the time, I asked where she lived (then the conversation took a different direction and I forgot to mention the parking passes), and I asked for her friend’s last name (was I trying to find out where she lived, too?). Then I invite her to a musical the first chance I get after only the second time I met her. Um… yeah, I look like a creep who had ulterior motives all along, which she’s probably experienced previously. Suddenly, every email I sent, every call, every question, was merely an insincere excuse to have contact with her. As soon as I saw it from her POV, I shot her a short email joking about it, clearing it up, and inviting her to sub. (Typically, when I have miscommunications, I just point ‘em out and usually they resolve.) Unfortunately, she still didn’t reply and so it probably served only to make matters worse.
Okay, as an expert, what do I do next? Nothing. I’m totally screwed. Any email I send her will be interpreted as an excuse to talk to her and stalkerish; however, if I stop communicating with her, it is proof that I was only interested in her all along because as soon as she declined the musical I stopped emailing and calling. Even if I email her to get the parking passes, it’s an elaborate ploy to connect. So, I’m damned if I do and damned if I don’t. All I can do is hope she sees me in volleyball circles on the beach over the summer, where she notices I’m having a lot of fun and socialize and play with a lot of women. (Hell, I even have several teams on which I’m the only guy!) Over time, along with a few friendly brief conversations on the beach, she’ll hopefully realize I’m not some sort of goofy, insincere creep-of-a-guy who just screwed up by showing his cards too soon. Actually, the entire incident will give me more insight into her personality–is she understanding? Does she take a moment to see the situation from the other side’s POV, as I did? I’m guessing “yes” to both of those, since I’ve already run into her a few times on the beach. She’s been friendly and social, although I could see she was a little hesitant and skeptical (probably a little afraid I was going to recite a sonnet I wrote for her or sing or something, revealing the love I’ve had for her since we met! Ah… no). It’s a little uncomfortable (actually sucky) for me because I can’t be my typical flirtatious and outgoing self.
So, if this happens to you, that’s my advice: sit and wait. Let the woman see you as your normal self and you’ll resolve any misunderstandings. Do not continue to send emails or call, trying to fix things–you’ll just look more and more stalkerish and she probably won’t even read the emails or listen to the voicemails. Do not ask mutual friends to put in a word for you–you just look non-confident (if they speak up on your behalf on their own, that’s fine; you just don’t want them to say, “Ian asked me to…”). I’m not saying it will be easy; it won’t. No one knows that more than me. I’m extremely tenacious (you have to be to get a book out, be one of the most sought comedians of your day, etc), so when I anticipate or see a problem, I want to fix it immediately. Remember, though, your actions will be met with a lot of mistrust by many women.
I must admit, it’s pretty sad for me to make such a basic oversight. I am usually very good about considering POV because I had to as a comedian in order to have some kind of normalcy in my life. (Most entertainers–musicians, comedians, actors, whatever–who start young in the biz never find normalcy in their lives; enter eating disorders, alcohol, and drugs. At most, you’re only on stage for a few hours a night. Without normalcy, how do you fill the rest of that time? For guys, you turn to drugs, aclohol, and empty sex; I wanted to avoid those pitfalls.) It’s the little things that provide normalcy, so I focused on them. I had to consider POV to be effective. My biggest challenges were birthdays, Valentine’s Days, and Christmases. I made sure I had a date for every V-day and my birthdays. Those are typically big deals for dates. They become amplified when it’s going to be your only date, you know? So I had to learn to work with women to get them to realize that they were just ordinary days and all was cool. I didn’t want them latching onto me and didn’t want them to think the date was something serious for me. Around Christmas, I like to hit A Christmas Carol at The Goodman Theater in Chi-Town. However, that’s a huge first date for a lot of women but when you’re only in town for three days and you want to see the show, see a woman you met, and see your family and friends, it’s not like you have time to have a date and see the show separately. I found success only by considering POV. Once you realize someone’s POV, you can usually squash it as being built upon nothing. For example, a date would think hitting The Goodman was a big first date loaded with pressure because of the price of tickets. So, I invited my date with a simple, “I hate to be cheap but let’s hit The Goodman for Christmas Carol.”
“That’s not cheap! Those tickets are expensive.”
“Naw, that’s only in your head. It’s like $100 to go; if we go to dinner and have wine, I can easily drop over $200. So, I’m being cheap and I apologize.”
That’s all it took for a woman to see the misconception about hitting a nice theater for a first date. So, you can imagine how stupid I must have felt when I realized my oversight with Sheree.
I’ve become good friends with women who I’ve had such miscommunications with and even dated some. Only once the issue wasn’t resolved and that was because the woman was immature, not understanding, and completely self-absorbed. In her case, I dodged a bullet; she’s not someone who would make a good friend or anything else. In any case, if you take the prescribed route, it will turn out for the better… although it may not seem like it right away.