Ryan McGuire/Gratisography
Source: Ryan McGuire/Gratisography

Annie just turned 40, and celebrated by inviting friends to dinner at an inexpensive restaurant. She was afraid no one would come to the party. She especially wanted Lenny to come, but Lenny was preparing for his next big adventure, and said he would come if he possibly could. She wasn’t sure what that meant.

Lenny works for a Jewish non-profit where his youthful command of Yiddish is a major asset. Everyone loves Lenny, who has confidence and charm, is warm, smart, and just a little bit odd—the right amount, according to Annie, who admires his red pants, electric blue socks, and gold tee shirt featuring a WPA poster for a 1938 production of a Yiddish comedy by Sholem Aleichem.

Annie works for a university press; her creativity and graphic design skills are a boon for the publication branch of a major research university. Everyone loves Annie too (though she doesn’t know it), and we revel in her wit and wisdom. She’s slim, wears snazzy hats, and has beautifully straight long hair. Annie, like Lenny, tends toward offbeat, humorous clothes in bright colors. (The fact that I always want to restyle her attire to make it “more becoming” is a sign that she is very, very cool.)  Both Lenny and Annie are comfortable in costume: they live their real lives on stage. 

Annie’s storytelling at an open mic several years ago was a foray into performance art that has evolved and burgeoned. She continued to perform at the open mic, and submitted a piece for a competition in which she was by far the best performer. Then one morning she surprised me by announcing that she had decided to drive an hour east to an improv class that evening. It took only one class session to confirm that improv was “what I was meant to do on stage”; the laughter she garnered motivated her to take herself, and what little money she had, to weekly classes in the program. 

Eventually she quit her stressful, underpaid jobs, packed up, and moved to be closer to the improv scene and “my people,” as she calls her fellow-performers.  She met Lenny when she had a temp job at the non-profit; her job ended, but they ran into each other several times. She liked him, and asked him to come to an improv show with her; he loved the show and invited her out for pie. Later she told me that, “When we’re together, we talk about everything. I don’t think about what I’m saying—it just pours out of me. We’re so comfortable together.” 

Aha! I thought. Love. I’m not always a matchmaker, but I do listen when a seriously shy person tells me that talk is easy, mentions the word “comfortable,” and says she doesn’t censor herself with a particular person. I liked the sound of Lenny. And then she told me that he was starring in a production of Waiting for Godot. “Which character?” I asked, and was certain of the answer. “Not the one who spouts philosophy. The one who eats the carrot,” she said. “Estragon. The poet whose feet hurt.”

The play was a resounding success for the small repertory company, and Annie went to see Lenny in it twice. The second time they could have gone out after the performance, but they missed each other, by minutes. Annie was bitterly disappointed when Lenny’s response to her congratulatory message was a quick “Thanks! In the city now, but let’s get together when I get back”—and then nothing.  No follow-up at all. 

We had a long discussion about communication via social media. Annie prefers texting, but Lenny prefers Facebook messaging. They both hate the phone, and email, of course, is too slow and cumbersome. We talked about what he was communicating by not following up on a potential date: did it mean he wasn’t interested? Annie was afraid it might, but I thought his proposal that they get together when he got back indicated interest. “But he tends not to follow up,” she told me. “A couple of weeks ago he mentioned a movie I wanted to see, and I said we should go see it together, and he said yes, but never said when. And the movie came and went.” I pointed out that he had been in the midst of an arduous rehearsal and performance schedule, and probably pretty absorbed in that. She agreed. “But I don’t want to always be the one who makes things happen.” 

Ah yes—one of the big dilemmas single women face these days: how much organizing, inviting, waiting, and finalizing should one woman do to go out to dinner and split the bill? Annie began to riff on the theme, and soon had me laughing and wincing as I recognized versions of myself in her comic depiction of modern dating. I asked if she had anything to lose by following up on his suggestion that they get together now that he’s back. “Just four dollars on a piece of lemon pie, or four hours waiting for his reply,” she said at last, smiling at her heroic couplet.

As it turned out, Annie messaged Lenny, who proposed dinner. Good. With a friend of his, Wally. Well, okay. And it turned out that it was a very fun evening: they went to a tavern with retro-trivia, and won. They sat outside after the place closed, “and talked non-stop for two hours.” Wally and Lenny had each parked beyond Annie’s car, so the farewells were communal, with warm hugs from both men. Annie felt comfortable, cared for, at ease. Excellent.

A week later she invited Lenny to her 40th birthday party, and he came. He stayed the whole evening, made everyone laugh, pulled Annie into line to get free popcorn to go with their soda. He was relaxed, and fit in with her established friends, old and new, and the report from the friends after the party was that he was “great!” “Gorgeous, if you like bright clothes—and we know you do, Annie!”  “So fun!”  

Annie told me she felt a little let-down the week after her birthday party, not only because the milestone had passed, but also because Lenny was out of town, off to Ann Arbor to visit his family, and then on to Quebec City to perform in a poetry slam—in Yiddish. Yes, she said "Quebec," "Poetry Slam," and "Yiddish"—all in the same sentence. She told me that she hoped she would hear from him, that he had said he needed to get a costume to wear at the slam, and she had told him she wanted to be a clothing consultant. I asked what he might wear for such an event, and she shrugged. “Something funny,” she said. “Maybe big shoes.”     

I looked at her, and saw a longing that Annie usually keeps under wraps. I can see that being around Lenny affects her just like being on stage does: she opens up, her humor pours out, and his enthusiasm chases away the rejection she still experiences from her alcoholic parents, who marked her 40th birthday with silence. 

I hope he will remember to message her when he’s working on his costume for the slam. For her sake, I hope he's not gay. I really hope that Lenny becomes Annie’s SRO crowd, her spotlight: a lifelong standing ovation for her, as she might be for him. 

I know, I know: “Matchmaker, matchmaker…”

Ryan McGuire/Gratisography
Source: Ryan McGuire/Gratisography

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