First, some background. I'm forty years old and have always been very shy. I've always been well liked by everyone who knew me, but for the most part, have not become a part of their lives. I've had one girlfriend, years ago.

Several months ago, I decided it was time to try to change all of that. This is an account of my recent exhilirating and scary initiation into the world of flirting.

This was written for my benefit, and to share the experience with a friend, who suggested that I share it here. Some of it was written in the middle of the extended period described, and some after it ended (the signifcant part, anyway). I've decided to leave it as it was written.
Except for my own, I've changed the names of the people mentioned here.

The Rebecca Chronicle


How Clarence Actually Flirted One Day, and Started Down a Path Which May Lead to Friendship (or More) (yeah, right)

Episode 1

It's Thursday evening, I'm seated at my table at Red Robin. A waitress who I haven't seen before appears at my side. I lay down the book I'm reading (Las Brigadas del Espacio), and look up to see what is possibly the most engaging smile I've ever seen in my life. According to the nametag, it belongs to Rebecca.

"May I bring you coffee, or perhaps some onion rings to start?"

Believe it or not, doffing my usual polite-but-all-business manner that I normally use while dealing with people during a commercial transaction, I start a conversation with her. I tell her of my dismay that RR no longer offers 1/2 orders of appetizers. She says I can get a 1/2 order of rings, but I mention that what I really used to like there was the cheese sticks. Sorry, she says, I can't get you a 1/2 order of those. At that point, I was apparently possessed by an alien spirit, because out of my mouth came "Well, maybe we can share an order some day". Rather than slapping me, she smiled again. I asked her for a strawberry lemonade.

Setting my drink before me, she asked "What have you decided upon?" That wording really made an impression. Said without affectation, simply elegant and yet from a wholesome-looking nice woman. Wanting to show that I noticed and appreciated it, I responded "I've decided upon the rib/chicken combo special, with cole slaw instead of fries. And could I get that on a plate?" (instead of in a basket) "Certainly." She also gave me a customer feedback card, and said I should mention my desire for 1/2 orders. I said I doubted that would do much good, since I would guess it was an economic decision to stop offering them and one customer wasn't going to change their mind. She said "Well, management does read them, and I'm management :)"

When she brought the meal, it had the default french fries. I was debating whether to mention that to her, when she says, "I'll be right back with your cole slaw."

The rest of my encounter with her that night consisted of just a few pleasantries. While eating, I overheard her talking to another worker there, saying that she would be working next Tuesday. Immediately, in the heretofore empty slot on my calendar for next Tuesday was writ "Dinner at Red Robin".

On the receipt, she wrote "Thank you!", as waitresses do sometimes. I added "Thank you, Rebecca", and left. I went over and over the evening in my mind. Obviously, I had taken to her easily, and it seemed that she had liked me as well. The problem was, how could I determine if it was personal at all? She is a very friendly person (though not obsequious; I can't explain why I don't see her that way, since I have a low threshold for thus categorizing a really gregarious person), and was, of course, just as friendly with her other customers.

Episode 2

Tuesday night. I walk in the front door, muster up my courage, and ask the hostess, "May I be seated in Rebecca's section?"

"Oh, Rebecca's not working tonight." I hope my face didn't fall too obviously, as her answer struck me like a boot to the head, and I felt so foolish.

"Well, in that case, anywhere is fine", I managed to stammer. "Anywhere" was the table way back in the corner, in Mary's section. I'm sure Mary is a nice person, but she's no Rebecca. So I eat my spinach/artichoke dip and read my book. When I'm almost done, I see Rebecca walking over to a convocation of waitresses near the kitchen entrance. They talk about schedules and such for a while. I see her look in my direction, and see that she sees that I'm looking in hers. She walks down the aisle, and when it's clear that she's coming to my table, I put down my book and smile at her (thinking, "Okay, let's get those BriteSmile(TM)'d teeth in action"). She said "It's Clarence, isn't it?". "Yes, Rebecca" I replied, being very sure to address her by name (and without cheating, since she didn't have a nametag on). We talked for a bit; she said that the spinach dip was one of her favorite items, and I agreed, noting that it's also better at RR because of the acoutrements that come with it (chips, carrot sticks, celery, etc). I was really happy, as it didn't seem unreasonable to assume that she wouldn't have done that if I was just another customer.

The next day, I told the whole story up to this point to my psychologist, and she agreed with me that it was a very positive sign of progress for me. I told her I actually wanted to ask Rebecca out, we discussed my fears of being seen as "hitting on her", etc. She assured me that it would be a very strange woman who took such a request as an insult. :)

Not knowing when Rebecca was working next, I was reduced to calling the restaurant and asking if she was working. I mentioned to Joanna that now I had added a fear that after a few days of this, the hostess would mention to Rebecca that some creep might be stalking her, because he keeps calling and asking about her. Oh well.

Come Friday or Saturday, I went without checking first. She wasn't working. Before leaving, I asked my waiter if he knew when she would be working next, taking the risk of personifying their image of the creep. He looks to be deep in thought for a few seconds, then says "No." I stifled the impulse to scream "Of course you don't, you moron, go look!" Joanna agrees that he didn't get the obvious implication.

Episode 3

This is the day. I'm gonna do it. I'm gonna ask her out (in my own way, of course). Finally receiving a "yes" to my telephoned question, I go to RR that night, and ask to sit in Rebecca's section.

I decide on the seafood pasta and a peach milkshake with no whipped cream. Excellent choice, she says; as she starts to walk away I comment on a pin she's wearing. She says a customer gave it to her. I see this as a good thing because she at least doesn't totally reject the appreciation of her customers. A few minutes later, the shake is brought to my table by another waiter, heaped with whipped cream (the shake, not the waiter). When Rebecca brings my food, she sees the shake, picks it up, and says "I'll be right back with your shake", and brings me one without.

We don't talk much while I eat, but I notice that each time she passes by, in addition to smiling at me, she rests her hand for a moment on the booth I'm sitting in, as though it were my shoulder, or runs her fingers along the edge of the table as though brushing my arm. At last, a verifiable sign that she is treating me differently than her other customers! I'm the only one to receive this attention. [Geez, how many guys get excited by a stroke of the table? :)]

At the table across from me is a group of two men and two women, couples I think; the men repeatedly ask Rebecca if she'll join them for a drink after she gets off work; she deftly declines. The whole group is in agreement that Rebecca is a wonderful waitress (which is true, of course). Even though they presumably had no ulterior motives, I really don't want to come off that way in Rebecca's mind.

Finally, I get the nerve to "ask Rebecca out"; after filling in another feedback form (in which I comment about the pasta dish, and under "Reason for your visit" I put "Rebecca!" (coming on too strong?)), I start writing a note on the back of my copy of the credit card receipt. I really should have thought to bring a piece of paper :) The high points of the message are

  • I've never done this kind of thing before, but you're such a pleasant person that I need to
  • I'd like to see you socially; I ask if she plays tennis, just to avoid the "whatever you wanna do" wimpy look
  • I'm sure I'm far from the first customer to want to see you, sorry if it's unwelcome
  • I leave my phone number
I put it in her hand as I'm walking out. Now the waiting, and the fantasies and the paranoia, begin.


She didn't come running out after me to tell me how much she appreciated the note :) She didn't call that night, or the next. Or the next. Or the next. It was the next Thursday (one week later) that I was in the shower in the morning, and heard a message being left on my answering machine. I couldn't make out the words, but it was a woman's voice, and it ended with a phone number. I jumped out of the shower and ran to the phone, totally dripping -- it was Joanna, calling to ask if she could change the time of my appointment that day :) Rebecca didn't call that night, either.

Episode 4

That night, I'm back sitting in Rebecca's section. She comes to my table, nice as ever, greets me by name, asks if I'd like a strawberry lemonade. She comes back with one, and asks if I know what I want, then says, "I'm sure you don't want the seafood pasta :)". (In the feedback form I filled out in Episode 3, I mentioned that I couldn't finish it because there was so much oil in the bottom of the plate.)

"That's true", I say, while pleased that she had read the form and remembered what I wrote.

"But do you realize that an Alfredo sauce is made with cream and butter?"

"Well, I couldn't have defined it as such, but I suppose so. But there was an awful lot of it!"

So, I tell her I'd like the tuna croissant. I add that every meal I've gotten from her, I had some special request; today's was "no avo or sprouts, but add some red onion". "No problem", she smiled. "Would you like some onion ring sauce with that?" (It comes with a few onion rings.) "Onion ring sauce?", I say confusedly. "I've never heard of such a thing." So, when she brings the food, she brings not only a cup of onion ring sauce, but also one of barbecue sauce, one of ranch dressing, and one of honey mustard sauce. This in a restaurant which in the past had been really miserly wrt requests for sides (though it's not so much anymore).

So I'm eating, and at one point she brings me another strawberry lemonade. I ask her if the waiters make the drinks themselves, and she says usually they do. I mention to her that she is the only one that puts the strawberries in on top of the ice. "Is that okay?" "Yes, that's definitely a good thing", I assure her, and she says "So you don't have to dig for them later". Yes, indeed. Not a word yet about the note, nor even an intimation that she had read it.

While I was eating, a manager and some other employee were having a bit of an instructional/orientational tete-a-tete several tables away, and I overheard her advising the young'un not to say "Do you need change?" to a customer when picking up their money. I decided to take that opportunity to get some talking-to-strangers practice. I walked over to their table and asked if I could interrupt, then told her why I was glad to hear her telling the employees that. After a short discussion, I retreated back to my table and back to my book.

A while later, Rebecca came by and dropped off a basket of french fries (which wasn't included in my meal) in passing; she didn't say anything (but of course the smile was there). Despite that my RR visits are generally later in the evening, after the normal dinner crowd has left, it was a bit busier than usual.

Eventually, the manager's session ended and she came by my table. She said something, I don't really remember what but probably something like "Is there anything else you'd like to tell me?", and we got to talking about various aspects of the operation. She said she thinks onion ring sauce is a RR thing. Here I am talking to the manager at my table with 4 cups of sauces for my three onion rings, a basket of fries, and (by this time) three strawberry lemonade glasses. I took the opportunity to laud the waitress-ship of Rebecca; Terri (I think that was her name) agreed that she's definitely a good one. I also worked in a statement that I really liked her, planting the possibility that it would come up sometime when the two of them were talking. After a pleasant four or five minutes, she thanked me and excused herself.

Later, Rebecca left the bill on the table. I left my credit card, and when she picked it up I mentioned that I hadn't been charged for the lemonade. She gave me her trademark smile, said "Thank you", and went off to charge my card. Looking at the charge slip she brought me, I saw that it still didn't include the lemonade. I flagged her down, worried how to bring it up without sounding bad, and said, "I don't know if you understood what I meant about the lemonade; it's not included here". She smiled and said, "I know." -- a pause and more smile [a better writer than I would probably be able to get the wonderfulness of her smiles across without repeating himself :)] -- "You're a really honest person." Then she continues on to her other tables. Oh well, what could I do. I signed the charge slip and, once again wondering how this would be taken, I gave her an almost $7 tip. I was thinking I should pay for the lemonade, though including it in the tip certainly didn't remunerate the restaurant, and could just provide a perverse economic incentive for Rebecca to cheat :)

Well, all the normal steps of the customer/waitress interaction had now taken place, and no mention of the note. What to do? What to do? I told myself I couldn't allow myself to just leave. I sat at my table, not reading, for about ten minutes, during which Rebecca made several trips between the kitchen and her other tables. Finally, I got up and walked by the kitchen and asked if I could see her; she walked over, and I, having failed to work out a good way to ask, just blurted out something like "I just wanted to check if you read the note I gave you last time." She said yes, she did, but that because I wrote it on a credit card receipt (even my copy), there was some rule that said she had to turn it in.

My brain went into high-gear: What became of it? I don't know. Does she or doesn't she have my phone number? I don't know.

She said "I didn't know you played tennis[1]". Well, she certainly had read it and remembered it. "Do you?" "I've played a few times in my life, but it's been a long time." That wasn't It sounds like fun, let's play, but at least she mentioned it. But it seemed to end there. I was getting nervous about keeping her from her work (and about not knowing what to say next), so I ended with something stupid like "I just wanted to be sure I wasn't out of line saying those things", which was supposed to elicit some comforting remark like Heck no, I'll call you some day; at least it got the "No" part. With that I ended with a good night of some kind, and left.

So, the big question remains unanswered. I told myself, "She was probably saying no without wanting to say no".

( Here's a coincidence. A couple of days later, I read this on Everything:

"Any sufficiently nice person is indistinguishable from someone who likes you." I have to disagree. There is a very simple way to distinguish between the two. "I like you, do you like me?" Anything short of a yes is probably a no. In case of a yes, be sure to confirm by asking the person out. Again, anything short of a yes is probably a no.
Noded by Mojo Jojo )

[1] This is why I don't get small talk. Of course she didn't know I play tennis -- she doesn't know anything about me! I would just feel stupid saying something like that, but it did keep the conversation from dying right there.

Episode 5

Events have conspired to keep me away from Red Robin for a week after that. On the eighth day, I went for dinner -- she wasn't working. From how the hostess said that in response to my question, it's clear that it hasn't been lost on her that I have an agenda :)

When I was ready to leave, I wanted to again see if I could find out when she would work next, but I wasn't going to make the same mistake as last time by leaving the waiter a way out. I said to him (not the same guy), "Could you do me a favor? Could you find out when Rebecca is working next?" He hesitated for several seconds, with a kind of I'm not allowed to do that but I don't want to say so look, then says "Sure, I can". He goes off and returns a minute later, and says, "Sorry, the schedules aren't up." I thank him and leave. Did he speak the truth, or did he not check but wanted to pretend that he had? I'll never know....

That's the story up to this point.

(The next day: I just called to ask if she's working, and the guy who answered the phone asked my name (which I gave him) and was going to go get her! I told him that wasn't necessary. Dinner at RR for me tonight...)


So there I am, in Rebecca's section, with my spinach dip and strawberry lemonade. I read a page or two of my book (Robots e Imperio), but can't really get into it because my mind is trying to figure out, without being rude, how to tell Rebecca something like Ok, I need the straight scoop, was that a yes, no, or maybe? Tell me, I can take it. Since there probably is no way, it's not suprising that I didn't come up with one.

Two people were seated in the booth in front of me, both of whom were deaf. I was interested to see how that would work; Rebecca handled it with equanimity. I heard later that she knows the alphabet in ASL; though she made a few gestures, I don't think they were mere letters. In fact, at one point she came to their table with a question written on a piece of paper [see, I'm not the only one :)], and they made a sign and she repeated it. I assume that she was asking them how to sign some particular thing, as she used it later. I think it might have been something like Can I get you anything more? That struck me as a very polite thing to do. (On the language front, I also heard her voice in the kitchen at one point; she is fluent in Spanish. The silly hopes section of my brain started manufacturing fantasies of my practicing with her on our future dates...)

Naturally, she brought me another strawberry lemonade at one point. It was difficult to drink much out of it because the mixture had so many strawberries in it (far more than the owners would like to have seen, I'm sure). She came around again and said "That's got a lot of strawberries in it", and went to get me another one. I probably had about two cups of strawberries in all. [A good thing about strawberry lemonade [at least at Red Robin, where it actually has strawberries in it :)] is that you get dessert for free :)] When she brought me the bill, again she had not charged me for the drink. I didn't make an issue of it this time.

I decided to take a little mercy on myself and wrote out my demand. It went like this:

    It seems likely to me that
    you have given me a polite
    "no" on the issue of us spending
    some time together.  But I
    don't want to assume that and
    be wrong.  I'm going out of
    town next week and it would
    prey on my mind if I didn't find
    It's ok to tell me "no" if you're
    not interested. :)

    Sorry to bother you at work with
    this, but it's the only place I
While I was procrastinating, the few remaining customers left, and the restaurant closed. Finally, with the guy vacuuming the carpet glaring at me, I got up to go. I waited near the kitchen until Rebecca came by. She was a bit taken aback (she probably thought I had gone already), and said to me "Did I do something wrong?". I don't know why she would think that, but I said "Of course not.... Could you look at this before I go?".

She looked at me strangely (I deserved that) and read it. I was shaking somewhat and my knuckles were white from clutching my book so tightly. She smiled at me and asked why I didn't just say it to her. I finally came up with just "It's very difficult". "It's ok to just say it. But I don't go out with my guests. Where are you going?" It took me several seconds to realize she was referring to my trip, so I told her I'm going to Washington, D.C., and we talked about that for a moment. Finally I said "Well, I'll see you in two weeks", and she said "I'll have the strawberry lemonade waiting!". I leaned close to her and whispered "But you should probably charge me for it :)". She whispered "OK", and gave me a little squeeze on the shoulder and I left.

Then I went to the office, cried a bit, wrote Nolan an email telling him about her "no guests" policy (I had seen him before I went there and he wished me luck), and broke a coffee mug :(

Fade to black

Voiceover Well, that was my first attempt at flirting. I feel good that I did it, and I have to be sure not to think of it as a failure. Now the question is, how long will it be before I try again?

Roll credits


No animals were hurt during the making of this story (except for the chicken, the cow, the shrimp, the scallops, and the tuna; nobody cares about the spinach).

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