Leelah and Jack

The following is the transcript for this podcast episode.:

Jodi: Leelah, thank you for being my guests this episode.

Leelah: So glad to be here. Love your podcast. And I’m really excited to be a guest today. Thank you.

Jodi: You’re a Seasoned Dater and for anyone who’s wondering what a seasoned dater is, it’s a term that I coined lovingly for adults who are in the dating scene for longer than they had anticipated.

Now I’m curious to learn more about you and would love it if you would share some of your backstory with us.

Leelah: All right. Well I am on the eve of my 50th birthday and I’ve never been married. No kids. I have done a ton of traveling and moved to a couple of different locations and I am a loving auntie and also really, really enjoy outdoor activities.

I have my own business as a nutritionist and health coach, and I just love being of service to people in that way. It’s a good life.

Jodi: That’s fantastic. A good life! We all want a good life. And I am happy to hear that is what you’re living. This date we are going to now delve into…who is the guy you went out with?

Leelah:  His name is Jack.

Jodi: What was going on in your life when you met Jack?

Leelah: Well, I had just three months prior ended a two year relationship that just ultimately wasn’t working, but it was a really hard decision. And some of the reasons for that is he was fine. There were lots of things that went well.

It was going okay. He had kids and I had wanted kids. But by the time we had met, I was a little past childbearing years, so that was enticing and we got along good enough. But I had had these ideas about what I wanted my long-term relationship to be like. And I had actually done a lot of growth work to be the kind of person who could have the kind of relationship that I wanted.

And I just wasn’t having that relationship with him. We weren’t really on the same page in terms of the vision of what’s possible. So I basically, I broke up with him and it was a really hard decision because I felt like I was launching off a cliff without a parachute late in my 40s.

Jodi: But you were brave enough to do it.

Leelah: Yeah. It took something. I’ll be honest.

Jodi: It didn’t take a parachute. You had no parachute, but you realized that deep down, you realized that if you stayed with this person, you weren’t going to fulfill the life that you wanted to live.

Leelah: Exactly. I wasn’t going to fulfill the life I wanted to live and I wasn’t going to have the kind of relationship that I had dreamed of and worked towards for quite a long time.

Jodi: How did you recover from the end of that relationship?

Leelah: Well, I got a lot of support. I had a coach and a therapist and they held me through it and girlfriends, once I got up the courage to do it. It was actually easier to be on the other side. I actually had some grief that I worked through even before I broke up with him. So once I actually did it in a way, it was, it was, it was easier. It was a relief.

Jodi: When you got on the other side of it, how soon thereafter did you think to yourself “I’m ready to meet someone who will create a relationship with me that will deliver me the life that I truly want?”

Leelah: Well, I wasn’t sure if I was quite ready when I met Jack and you know, it was a little bit of a thing when I first met him. Am I ready to do this? Am I clear enough? And I just, I decided just to take it one step at a time because I had already taken this brave step and, and left that other relationship. And so I wanted to be open to what there might be out there for me, but really it was just taking it step by step and really feeling in to myself and how I was doing at each point. So I just took it step by step.

Jodi: How did you and Jack meet?

Leelah: Well. It was, the meeting was a little bit drawn out. So I attend a spiritual center and, let’s just say that that not very often, are there men in the age range that I’m looking for that are probably straight who show up at this place. So he arrived one morning and it caught my attention for sure.

And so, I met his eye across the spiritual center and I know he caught it and he nodded to me, and there’s a point where you can introduce yourselves to each other. And so we did that, but there’s not time to talk at that point. And then after the service, there is time to talk, but he didn’t approach me at that time. And I was like, “you know what, I’m not going to be the one I’m not going to do it. I’m not going to be the one to approach him. He, if he wants to do it, he’s going to come to me.” And he didn’t. (Laughter)

Jodi: And then what were you thinking?

Leelah: Well, I was like, I guess, any number of things “he’s not interested, I’m not ready. It’s not meant to be….whatever.” So we both left the spiritual center that day. That was a Sunday. And then the following Friday, one of the people was hosting “A Spiritual Singles Event.” It was the Friday after that. I decided to attend that and it turned out that the, the door to the facility was locked.

And, so I was kind of waiting out back and I had my rotisserie chicken in hand and was making calls and trying to figure things out it was a potluck. So along comes Jack. With his rotisserie chicken and hand. So we’re hanging out there behind the spiritual center with the rotisserie chicken, you know, the double rotisserie chickens.

And since I had been at the spiritual center longer, I was making some calls and somebody else showed up and we got in. And it turned out for this event that the only people who attended were me and him and the facilitator and then one other woman who was older than our age range. And that was it. So, I was like, “oh, isn’t this interesting?” (Laughter)

Jodi: You went from being across the room, doing the “catching of the eye” thing with all these people in between you, to being in a much more intimate setting where you somehow completely were in sync to select the same food for a potluck that only four of you were there to attend.

Leelah: I guess that was a good sign that we selected the same food. (Laughter)

Jodi: It seems like it was. Yes. Well what happened next?

Leelah: Of course, we wound up sitting next to each other in the circle. You know, I didn’t make sure of that or anything, but it was pretty easy to do without being obvious about it. And the neat thing was is that the way that this event went is that the facilitator asked us, the group, some very deep questions about being single and dating and finding people that are spiritual. And we shared in the small group, and then there were moments where they had set us up in pairs. So I was paired with him and we shared prompts to questions and we shared with each other and you know, and then they’re like, “Hey guys, come back to the group and we’re continuing to talk.”

So, because we went so deep in our conversations that first time without kind of the pretense of it being a date or anything, it, I sort of feel like in some ways that was, that was part of our first date. So it was the way that we got to know each other on a much deeper level then we might have, if we’d met online and the first time we saw each other and all the nervousness and all of, all of that.

So because there wasn’t that like first date pretense, and because the facilitator gave us prompts that prompted us to go pretty deep in our conversations, it was really neat to get to know him on a, on a deeper level, straight off the bat.

Jodi: This is so interesting because when you think about what a typical first date is about, it is about getting to know the other person, asking questions that give you a hint about them, but it’s rare and sometimes not appropriate to go very deep into topics that are very personal when you’re on a first date. That really often is going beyond what is needed or comfortable in that sort of setting. But here you are an entirely different setting and you have a facilitator who is guiding your conversation and requiring you to go deeper than you ever would on a first date.

I am curious how you felt doing that because you’ve already alluded to the fact that you were attracted to this man? How did you feel disclosing things about yourself that you probably would not have disclosed on an actual first date?

Leelah: Yeah, that’s a good question.

I think it was sort of like, there were moments where I checked in with myself and I was like, “oh, okay, should we edit it or whatever?” And then I was like, “No, Leelah, just go with it, just go for the ride.” Because if I was willing to go deep, then perhaps he would have been as well.

And that’s actually what happened. It was a very connecting conversation in a way that if I was asking him whatever about his history or any number of the surface things that you might talk about on a first date, the, the things that we were talking about went so much deeper and they were so much more intimate than we might’ve had on a typical first date. And by the way, one of the things that I was wanting.

One of the things in my vision for a relationship is somebody that who could go deep with me and who was willing to be vulnerable and who could cultivate intimacy beyond the bedroom, you know, through conversation, through sharing of what matters to a person,

Jodi: He was already showing his ability. To converse with you in the way that you wanted a man to, without realizing that he was addressing needs that you felt you had for the next relationship that you were going to be in.

Leelah: Exactly. And I was like, weeeee! (Laughter)

Jodi: Now you just needed to get a date scheduled to you.

Leelah: That’s what we should talk about next.

So at the end of the evening, this was a Friday evening, he asked for my number. And of course, Friday evening, maybe Saturday morning, but I don’t think it was Saturday morning. I looked him up online and I realized that we had… I forget how many…it was close to 20 Facebook friends in common.

And I saw that one of my best friends was one of his Facebook friends. So, of course I called her up the next day. Now, mind you, he hasn’t asked me out yet. So I called her up the next day and I said, “Hey, this guy, Jack, he’s your Facebook friend, tell me a little bit about him.” And so she did, and he’s more of an acquaintance for her.

Basically, my besties were his acquaintances and his besties were my acquaintances. So there were any number of times in social situations that we could have met previously, but we hadn’t. So I asked my friend about him and then of course she proceeds to, without my knowing, she proceeds to call up one of his besties.

Interestingly enough, she scheduled a dinner on Sunday night. So this is two days after he asked for my phone number. He hadn’t called me yet by Sunday night. So I’m at a dinner with my bestie and one of his besties. And she has like already filled his bestie in, on all these things. And so it was so awkward because his best is like, “Ooh, well maybe the three of us could get together some time.” (Laughter)

And I’m thinking, oh my God, this, this stinks so bad. I haven’t even been on a date with this guy. And it was, it was very uncomfortable to say

Jodi: I get it. The cart was way the heck in front of the horse, on this one.

Leelah: Exactly! Yeah. Yeah. And it was embarrassing. Cause I guess of course he would expect me to check him out or whatever, but now all this had been in motion before we even knew what we were beyond a couple people who had shared deep thoughts, two nights.

Jodi: And rotisserie chickens!

Leelah: And rotisserie chickens. Yes. (Laughter)

Jodi: I can imagine you were concerned that he was going to be feeling pressure from his bestie to move forward and contact you and set something up.

Leelah: Yeah, it was just I’m, I’m a bit traditional and I like for the guy to make the move, you know, I just wanted to give him the space to do that without feeling like people were on his case. I just wished that that whole thing had not transpired

Jodi: At the same time, it spoke a lot about the people in your life and in his life. Didn’t it?

Leelah: Yeah. And I  did appreciate that we had mutual friends and that we choose to hang out with similar types of people, because that was actually another issue with the man that I had recently broken up with. I just didn’t really like his friends. So I’m like, okay, well this is a good sign. At least we’ve got friends in common and I know his bestie. He had met her before and all of this, so yeah, it was a good.

Jodi: It’s important to like most, if not all of the friends that one’s partner has in their lives, you’re you learn a lot about the person in your life, by the people who are in their life, don’t you?

Leelah: Yeah, for sure. And who they choose to surround themselves, says a lot about who they are.

Jodi: It does. Okay. So this dinner on Sunday night comes to a close then where do things go from?

Leelah: Well, finally he called on Monday. (Laughter)

Jodi: No texting. He called.

Leelah: actually I think he texted first, but then, but then we talked, we talked on Monday. So, yeah, it was a little bit of a nail biter before that while also feeling embarrassed. But I talked to him on Monday and then we made a date for the following Friday night.

Jodi: How were you feeling after that?

Leelah: Relieved. Yeah, relieved and excited because there was all this buildup.

Jodi: Was there this sort of buildup for him?

Leelah: I don’t think there was quite same built up for him. He was sort of the recipient of some buildup because his friend is like, “Ooh, guess who I had dinner with?” “Leelah, you know? But let’s just say there was a lot, there was a lot of buildup for me,

Jodi: Friday rolls around. Take us through what happened Friday night.

Leelah: Well, we had plans to meet out at a bar. We actually lived either side of the same neighborhood. So we picked a place that was close to both of us. That’s another thing we lived basically in the same neighborhood and we’d never met each other before.

And we’d both lived there at the same time for eight years. We went to a bar that was close by and the NBA finals were on. The two teams that were playing were his hometown/where I currently live, and then my hometown where I grew up.

I was nervous. I made this big thing. I’m like, “my team’s playing your team, but I’ve been gone for a long time, so, you know, I’m sort of a fan of both.” I wanted him to know that I wasn’t going to embarrass him by cheering ultra-loudly for the opposing team or showing up with my face painted with the wrong colors.

Jodi: Got it. I take it he’s a sports fan

Leelah: Yeah. And, and he’s, he’s very devoted to his basketball team. He’s been a long-time fan.

Jodi: Clearly you had thought a lot about how the dynamic was going to work between the two of you around the competition going on on the TV screens with the NBA finals happening. Let’s step back and tell us about how things went when the two of you saw each other at the bar after you both arrived.

Leelah: Yeah. So he was there first and it was really sweet, actually. He’s a very warm person. He gathered me in a big hug and it felt really good. And at this point we knew each other a little bit, so it wasn’t quite as nerve wracking as a, as a first date might’ve otherwise been.

Jodi: And how did things progress from there?

Leelah: Well, the game hadn’t quite started yet. And the food at the bar that we were at. Was not that great. So we ended up just kind of wandering around the neighborhood a little bit and we found a Greek restaurant and it was, it was a sweet little place. It was fun too, because I actually was going on a trip to Greece three months from then. So it was fun to talk about that and it sort of prompted conversation about travel and we’ve both traveled a lot. So I think the context of where we ate and opening up that conversation helped us.

Jodi: On the topic of conversation, the two of you had had a very in-depth and personal conversation the week before. Here you are back together again, did you find that the conversation eventually got to a deeper level, because that had already kind of been established as a comfortable place for the two of you to be, or was it more of your higher level, get to know you sort of…I’m going to say “chit-chat” that more commonly happens on a first date.

Leelah: Yeah, it was more the latter. I mean, I sort of felt like from my perspective, we went into that deep dive and I kind of wanted to catch up a little bit. I was like, “Who is this guy? What’s he all about?” That’s that sort of thing. Some of the basics that we hadn’t really covered yet. Yet at the same time we had had that deeper connection already.

So, we already knew that there was some sort of connection. So, yeah. And plus the context, you’re watching a game doesn’t really make for the ability to have super deep conversations. So honestly it was perfect. It was perfect.

Jodi: I love hearing that after the dinner was over did you go back to the bar?

Leelah: Yeah. So we went back to the bar and we watched the game and I cheered a little bit, although I didn’t have much to cheer about.  His team won. I was fine with that. And it was good. It was light and comfortable, just kind of having little conversations between the plays and it felt really good.

Jodi: What did you learn about him as he soaked in the victory?

Leelah: Well, it’s interesting. He understated it a little bit. He was really excited, but he understated his excitement a little bit. 

Jodi: So you learned he was very caring?

Leelah: Well, actually, yeah. Given that he is such a fan of that basketball team, I thought he did a really nice job of being attentive to me and connecting with me as well as, you know, watching the game and paying attention to the game. So it says a lot about who he is that he was able to do.

Jodi: How did the evening come to a close?

Leelah: The game was over and it sort of felt like the evening naturally came to an end. So he walked me back to my car and gave me a big hug and a kiss. And he, he asked me out right away for the following weekend. That felt really good, especially when the lead in was a little bit more waiting. It was good to, to not have the whole week to sort of wonder.

Jodi: Yeah, it is always good. Not to have to wait and wonder. Let’s go back to that kiss. Was that a kiss that really punctuated the first date and the preamble to the first date?

Leelah: Yeah. Well, you know, it’s actually is the kiss and the embrace. Jack has a really big heart and you feel that when you’re with him. Yeah. You feel it in all the ways. You feel it in the kiss, you feel it in the embrace, you feel it in who he is. He shows up as he’s, he’s just a very big hearted person and that was super apparent from the beginning.

Jodi: You’re sharing this implies that the two of you are still together. So my next question is, or really my next request is,  that you fill us in on the rest of the story.

Leelah: Yeah. I think one of the interesting things was, is our conversation at the Greek restaurant. So I had scheduled this trip to Greece, but I had dreamed for, oh God, probably 15 years of going to the Greek islands with my sweetheart. and my sweetheart hadn’t showed up. And so I just booked the darn trip. I’m like, “enough already.” However my sweetheart was showing up. So I took a chance and invited him to come to Greece for part of my trip.

And it was it was super romantic and I’m really glad I took the chance on it, cause it was about three months into our being together. And we just had our three year anniversary of our first date a couple of weeks ago.

Jodi: Congratulations! Wow! What a tremendous tale! What did you take away from your first date with Jack that has carried with you since that encounter?

Leelah: Well, I think there’s, there are two things. One of them is along the line of…what I would share with people who are still dating is to be brave and don’t settle for something that doesn’t feel right or that’s not what you want for yourself. I’ve never been married. I waited a long time and thank God.

And the other thing I would say specifically about the first day is to be brave enough to be open to share yourself, share who you are. Have an open heart. Be wary too. Cause there’s all kinds of things that we can encounter on a first date, of course.

But I think the fact that I was able to show up and to go deep and share who I was and not be scared was, was really powerful.

Jodi: That is, it’s not always easy. It usually isn’t until you get to a point in life where you just say, I’m going to do this and I’m not going to worry how it’s received.

Leelah: Yeah. Yeah. I’m over 40. I’m not over 50 yet, so I think it’s gonna get even better over 50. But I did notice over 40 that it’s like, not worrying so much about what people think and not hiding myself so much as I might have when I was younger. And I think it’s actually a really beautiful thing about dating later in life because they can see what they’re going to get.

And, we may be a little bit more confident in ourselves and hopefully they’ve matured enough that they have greater skills. And you can decide more quickly if there’s a connection or if there’s not.

Jodi: When I started this episode off, I started it by stating that you’re a Seasoned Dater.

How do you feel now at this point about being a Seasoned Dater?

Leelah: Yeah, I’m glad I waited. I’m so incredibly grateful when I think about the men that I could have married, because I thought that I should be married by a certain age. And when I think about being with them…they’re fine. Good good men. But it’s not like this.

And I really do feel I had this idea of what I wanted a relationship to be. And I did not learn it from my parents and I needed the time to grow myself and have the relational experiences that maybe were super challenging or, or grew me to be able to. To this point to have the kind of relationship that I have.

I feel like – Jack and I have talked about it –  even if we had met 10 years ago, there’s no way either of us would have been at a level of development to have the kind of relationship that we have. And so it’s so worth it to have not given in early and settled for something because that’s what the culture said I should do.

Jodi: I applaud you for staying true to yourself and figuring out along the way that it was the right thing for you to continue forging forward until the day came, when you meant that right person. And to not settle. And then one night when you had a rotisserie chicken in hand, you got the opportunity to really get to know a man who has turned out to be that right person. And who made your dream of a escape to the Greek Isles with a sweetheart come true. Bravo!

Leelah: Oh, thank you. It sounds so lovely to hear you say it. I appreciate the reflection.

Jodi: And I appreciate your coming on this episode to share this tremendous tale about being true to oneself and by being true to oneself, being able to chart a path that ultimately led you to the person who you were meant to be with.

So thank you. Thank you, Leelah, for being my guest and for sharing this tale with me and with the listeners.

Leelah: My pleasure. So good to be here. Thank you.