In this episode, Jimmy squirms good-humoredly under Alanna’s dating related questions: what does he do to prepare for a date? What bothers him on a date? Both hosts share some thoughts on the topic before moving into the meat of the conversation – humor and intimacy. What prevents us from enjoying another person within the context of relationship? What does taking oneself too seriously stem from? Tune in to hear what Jimmy and Alanna have to say about this endlessly fascinating and puzzling topic.

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Jimmy starts by saying he has a funny feeling that Alanna has a question for him. “Indeed I do,” she says, and dives right in. “Do you have a preparation ritual before a date?”

Jimmy stalls for a moment, bringing up how earlier in the day he overheard Alanna, Jessamyn, and Marisol exchanging stories about worst first dates. He then makes his way back to her question. “If I look back on my last five or six first dates, every single one of the girls either lived in another country or another state. And as for prep – I don’t have a prep.”

“Do you buy a plane ticket?” Alanna asks teasingly.

“Yes – I definitely think about the logistics. But I don’t think much about what I’m wearing. I don’t really even plan things that far in advance.” He brings up how one first date involved spending the day at a theme park, which he says is a good “friendly and fun” way to spend time with someone when you don’t know them too well. By the end of the day, you’ll have a fairly good sense of whether or not you have chemistry with the other person.

“Chemistry is important. You have to be attracted to the other person,” Alanna says, “To enjoy their presence. Another question I have, while I still have you under the microscope: what’s something that bothers you that women do on dates?”

“I don’t want them to be easy to get,” Jimmy says. “I want them to be confident, so that I almost feel that they’re not obtainable. I don’t want to know how interested she is. I want to have to fight for it – to win her over. If I won her over on the first date, I’m going to be too bored to come back for date two.” He pauses. “Does that sound harsh?”


Alanna replies that getting too bored too fast could potentially be problematic, but she agrees wholeheartedly that confidence is attractive. “You don’t want to date someone who’s looking for their identity in dating – or in you. It’s too overwhelming. Rilke talks about the importance of appreciating one’s distinctness, and the distinctness of other people. In our culture there’s a common myth that when you’re in love, you melt into the other person: but nobody really wants that.”

Jimmy agrees. “A lot of popular music – the fantasy genre in books – the disillusionment a lot of men feel – I feel like this is something that’s happening on a cultural level,” he says, in regard to the codependent model of relationship. He begins to segue into the conversation about humor and intimacy when Alanna stops him.

“I did want to tell you what bothers me on a date,” she says.

“What bothers you most?” Jimmy asks.

“When the man doesn’t ask questions.” Both begin to laugh.

“So keep that in mind,” she says – “When a woman asks you questions, she’s hoping you’ll mirror that back. But not just parroting the same questions. The other thing that bothers me is when I get in my date’s car and they’re playing a song so loudly that you can’t even converse. I get it – they’re excited, or they want to share the music they like – but it’s too loud to talk.”

“That’s pretty dumb,” Jimmy says. “Even I knew that. I didn’t know about the mirroring the questions thing, though.”

“Yes – specific questions,” she says. “Like – ‘do you like cheese?’”

“I often find I get too serious too fast,” Jimmy says.

Alanna agrees. “When I get nervous I get very serious. Why do you think that is? What prevents us from enjoying the moment?

“Well, a lot of insecurities might be rising to the surface,” Jimmy says. “Maybe some skepticism, too. I’ve had a lot of first dates – I don’t have very many second dates. Most go from first date to really serious, and then not worked out.”

So your history is at play when it comes to first dates,” Alanna says.

Yeah – I put too much pressure on it. Can’t just have fun.”

“I find that happens in a lot of different areas in my life – where I don’t give due credence to the fact that the present moment really is the only thing we have. Granted, our pasts do contribute to the people we are sitting here now. Sometimes when I’m brushing my teeth and  I look in the mirror I’ll be struck by my contingency, and all the ancestors behind me who contribute to my existence.”

“With which hand are you brushing your teeth when these thoughts come to mind?” Jimmy asks.

“The right hand. The thoughts that come with the left are so out there I can’t even tell you about them. But. I think that this sense of existential concern – this worrying about what’s come before, what’s behind me in the past –  can prevent me from appreciating the here and now. It can paralyze you.

Jimmy mentions how even in friendships, professional or otherwise, the tendency to be too serious can arise. “Humor and encounter go hand-in-hand beautifully,” he says.

I think when seriousness shows up a lot, it’s related to shame. It’s a defense mechanism. And i think shame and pride go hand in hand, too. When you’re ashamed, and you feel like you’re not worthy to be present or be heard, you withdraw, get really intense, and become more forceful than necessary – because you feel like you need to prove something. You stop resting in that childlike ease. So the thing is to get back to that original, native stance – of knowing that I belong – but without having to constantly look at that question. . . I’ve been told I’m too sensitive, too intense. Intense is my ‘trigger word’. And it’s bound up in that shame, and it comes up in the dating game. The worry of being too much, not enough.”

Jimmy shares about how seriousness “on his own behalf” usually arises from a place of insecurity, whereas seriousness toward others – a sense of responsibility and duty – is borne out of a more life-giving place, a place of love. He mentions how he takes what Love Good does seriously, because it involves real people with real needs. “My great grandfather used to always say – take what you do seriously. But don’t you ever take yourself seriously.”

“There’s a lot of freedom in that. Kind of like these conversations we’re having. We don’t really know what’s going to come out of our mouths, and it’s a great exercise in just being present.”

Listen to Eric Cyr’s song “Autumnal Waltz” and Lindsay Clark‘s song “Little Dove” on Love Good’s Exclusive Fall Sampler!


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Alanna-Marie Boudreau
Alanna Boudreau

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Alanna Boudreau is a writer, speaker, lyricist, pianist, and guitar player. She has recorded and produced five albums and lives near Philadelphia.