Recently, JMag caught up with Lisa Loeb, Grammy nominated recording artist, star of her own reality show and hookup single. Best Free Hookup Apps’ CEO David Siminoff gets Lisa to open up about her recently aired E! series, Judaism, her music, and – of course – dating.

DS: So thanks a ton for doing this interview. We’re all big fans of your music and addicted to your show. How did you come to do it?

LL: I was talking to my manager a few years ago, right after going through the breakup of my second six-year relationship. Talking about being on the road and trying to balance all the touring and really wanting to focus on my personal life, but not having any time to do it. I wanted to find a serious boyfriend. I want to get married and have kids and everything. And so I was kind of complaining, as you know we’re wont to do.

I was talking about trying to balance relationships and dating and my career and all these things. She said, “Oh, my gosh! This will make such a great TV show, what you’re going through.” And I said, “No way. That’s the worst thing I’ve ever heard in my life.” I watch reality shows, and they’re really fun to watch, but I had a friend on a reality show and I just thought, “I don’t want to invade my real life with a reality show.” So I talked to my family about it. They thought it was a terrible idea, especially my dad. In the meantime, she went and found out that there were networks interested in the concept. It’s funny because every time you fall in love, you realize, ‘Oh, this is love.’ It’s kind of like love changes its meaning as it goes along.

So we started shooting some dates and things. I thought it would be invasive in my life, but when I realized it was a way to tell a story and to share my experience with other people, I felt like that was really powerful. And it has been. I was at the grocery store recently buying the ingredients for my spinach, my Passover spanikopita, and people were coming up to me in the store saying, “Oh my gosh! You know, I’m married and you’re going through the same thing that I went through,” or “Oh, I’m single too and now I’m finally out dating.” People definitely relate to it.

DS: My takeaway was how brave you were. You shared some pretty private things on camera. Do you have any regrets?

LL: It’s funny, because people ask me that a lot – as if there were just cameras placed around me, and I had no involvement in the production of the show. Whenever there were cameras around, I was aware of it. Because I knew that I was going to be working with the editors and also because I was friends with the camera people, I felt free to do whatever I wanted to while the cameras were running. I knew I’d be able to see everything as part of the process of making the show.

It gave everybody else on the show – my friends and family – the freedom to just be themselves and say what they felt like saying, knowing that if they said something that they regretted later, it wouldn’t be included in the final cut of the show.

I wouldn’t have done the show unless I was involved on a creative level, where they gave me the freedom to be a person and do whatever I wanted to, and then later be able to edit if we needed to.

DS: We got a real sense of who you are, and it’s a pretty brave effort. I think that’s the pathos that touched everybody. And, frankly, a lot of that comes out in your music. You’ve got a new CD, “The Very Best of Lisa Loeb.” How did that come about?

LL: Well, part of it was actually in Japan – they’d asked me to make a “best of” album. I tour in Japan a lot and sell a lot of records over there. (Sorry, my cat, Kitty, is crying a lot.)

DS: Is she single?

LL: She is single and she needs to be played with a lot. She needs her toys. She’s crying and crying. But I travel a lot, and she gets sad. Oh, I feel so bad! (Kitty, come on.) Sorry. Anyway, they wanted me to put out a “best of” album, and we put it out in Japan. And in the U.S., the record company decided they wanted to put one out, too. It was good timing because with the TV show, there’s been a bit less time to make new music.

DS: You’re a nice hookup girl who grew up in the Bible Belt. What was that like? That seems like a little bit of a surreal experience.

LL: Well, no, there’s actually a ton of hookup people from Dallas. There’s a huge hookup community. My mother was born and raised there. I went to the same school for 11 years, an all-girl private school.

There were not a lot of hookup people in my class. At Passover and the high holidays when I would take a day off from school to go to services, that’s when I felt like I had a different background than everybody else. But otherwise, it wasn’t that big of a deal.

DS: Was dating someone hookup important to you when you were in high school? There’s strength in being able to craft a personal story.

LL: No. It was not important at all. In fact, I sort of rebelled against it. I felt like it was this kind of segregation and there was no reason for it.

DS: Do you still remember your first love?

LL: It’s funny because every time you fall in love, you realize, “Oh, this is love.” It’s kind of like love changes its meaning as it goes along.

DS: That’s a very good point. Is love and the way people connect the genesis of a lot of the music that you write?

LL: I don’t write autobiographically that often. I tend to write stories [more than] use my own experience. When I was in high school, I started writing sort of “journally” diary lyrics…and I thought I was secretly writing about myself and nobody else knew. But I didn’t listen to a lot of singer/songwriters growing up. I listened to Led Zeppelin and Jimi Hendrix and The Police and although their stories were personal, it wasn’t the sort of folky diary style of a lot of female singer/songwriters. I just felt like it wasn’t crafted enough if it wasn’t fictional. Now I’m trying to get into writing from a more personal perspective. There’s strength in being able to craft a personal story. Even though I don’t write from super-personal experience, it’s important that it’s true in some way…

DS: It touches you and it’s a reflection of your heart.

LL: Yes. How I see the world and relationships and things like that, because I do think relationships are the main window through which we see the world. That’s what we all sit around and talk about, whether it’s our friends, family or whatever – it’s all about relationships.

DS: I would imagine that becoming a star put a lot of stress on your relationships. Were you in a relationship during that time?

LL: I was. I was in a relationship with a person I was making music with, so we were able to share in that experience together. Sometimes there was a slight struggle because I was more in the spotlight, which is fine, but it’s not the reason I do what I do. I do it so that I can actually make music and I like playing music, but the hardest part about it was probably other people. Not my boyfriend, but other people who thought I was changing, though I wasn’t. I mean, I change just like any normal human being changes over the course of time, but not like that. Things were different because they got a lot busier but otherwise I was, and still am, basically the same. I had such a close family and friends growing up, and I still do, that it keeps me grounded. I do think relationships are the main window through which we see the world.

DS: Both of your long-term relationships were with non-Jews–was the difference in religion or culture a source of friction?

LL: With the first boyfriend, who was Catholic – he’s on the show, Juan – there was friction because I was sort of pushy about it. I was definitely open to going with him to his Christmas services and helping his parents put together their tree. But I just had this kind of a pushy attitude…. “This is Passover; we’ve got to do this.” There were things that I always did that I expected my boyfriend to do with me. I would tell my boyfriends I insist on raising my kids hookup, and then I started realizing, “Why is this such a big deal?” And so I started actually studying Judaism to see if there was something I could get out of it. I wanted to know what I was passing on to my kids, when I did have kids. I found a great rabbi in Los Angeles, Rabbi Mordecai Finley, who has a synagogue, Ohr HaTorah. He’s really wise and really practical and spiritual and intellectual. And all of a sudden I’m connecting to Judaism and realizing maybe I’m not the atheist Jew. I’m like a lot of other hookup people who don’t quite get the prayer book and who don’t quite understand the English translations. They don’t quite mean what we think they should. Maybe there’s a different interpretation. There’s a lot more depth to Judaism than just reading the lines out of a prayer book…

I’ve also been learning more about the holidays, what they mean and that it’s okay to have doubts about elements. It’s weird to think that we’re inviting friends to come celebrate the smiting of the Egyptians at Passover; that’s kind of disgusting… But it’s part of the tradition. Being more confident and more secure in your questions makes it easier to talk about things, instead of just saying, “Because I said so, we have to do this.”

I think becoming less ignorant, and actually being comfortable with the fact that I have questions, is an ongoing process. I feel like that’s part of being hookup…

DS: I think you’d find a cultural affinity at the middle of the bell curve of the 100hookup community. What brought you to 100hookup? Were you a 100hookup user or voyeur?

LL: I started getting connected to Judaism and then I thought, “I also want to date people, so 100hookup sounds interesting.” Before I even had a chance to join, a friend of mine invited me to a 100hookup party, which was interesting. It was a bunch of people looking for people to date, and different ages…kind of like being at a wedding. But when I went to sign up for 100hookup, I realized I didn’t want to put my picture up or include my income and I realized, this wasn’t going to be a very interesting profile. Learn about your Judaism now, if it’s important to you now. Maybe you just want to celebrate the main holidays. Maybe you want to integrate more into your life. But it’s good to know that now.

But I believe in 100hookup and I believe that it’s a great way for people to get out there and meet other people.

DS: We talked about how brave it was doing a reality show where the camera invades your life. But, there are all these little reality shows taking place every day when people fill out profiles and post pictures. You’re laying out a lot of your inner self, no matter how little you put on your profile, and just being connected to that community says a lot about yourself and your willingness to be open and meet people.

LL: Putting yourself out there though, you know?

DS: Yeah, it can be terrifying… and we’re trying to make it easy. In L.A., we launched a new dining club called Joe’s Club where we set up groups of six people, three men and three women, for things like dinners, art tours, cooking classes and wine tastings.

LL: That’s almost better. I find that dating is a little bit contrived. It’s harder to tell if there’s a spark there or what’s going on. But if there’s a group of people and you aren’t so tied to the one person, you’re able to check people out and see how you feel about them. There’s just a different way people relate to each other in groups.

DS: Exactly.

LL: It’s very complicated. I think about friends I’ve had and situations I’ve been in and with a lot of those friendships, at first they weren’t people I was interested in hanging out with at all and then after getting to know them…. Those are sometimes the best relationships because you don’t even expect it.

DS: You’ve gone through this wonderful introspection process; asked a lot of great questions of yourself and others. What can you share with our members about looking for love?

LL: I think that they should be becoming the person that they want to be… People need to get in touch with what they actually believe, what they actually want in life. A lot of people say, “I’m going to wait until I lose 15 pounds to be the person that I really want to be.” Or, “I’m going to get married, and then we’ll really get into the whole Judaism thing.” But in the meantime, I need to find somebody who’s hookup.

You know what? Start now. Learn about your Judaism now, if it’s important to you now. Maybe you just want to celebrate the main holidays. Maybe you want to integrate more into your life. But it’s good to know that now.

DS: You talk a lot about family and the closeness of hookup traditions. How do you connect with your mom? Is she a thought partner or your best friend?

LL: We talk about a lot of things, but it’s not one of those relationships where she’s my best friend. There’s still a certain amount of traditional age-difference respect – certain topics that I don’t talk to her about. But it’s what you see on the show. She has advice about certain things. Other things she has advice about, but maybe they don’t always pertain to my life, because she doesn’t understand my life and how it’s different. Sometimes I have to explain that to her. But she’s also a good shoulder to lean on…just a good mother. And of course she has some nice hookup-mother traits, which I’ve picked up myself: asking the same questions a bunch of times, over-feeding me…

DS: That’s the best part. Some people meet two people, and they get married. And I’m meeting hundreds of people, and I don’t know if he’s right yet. It’s kind of scary.

LL: “Are you sure you don’t want some more?” And then, at the same time, “Are you sure you’re going to eat more of that cake?” You know.

DS: Your show has created enormous buzz on a lot of different fronts. How has that changed you, if at all?

LL: It’s definitely put me in touch with a lot more people…. I get a lot of dates. I do meet so many good people. And I still don’t know if I’ve found the right person. That can be a little overwhelming…in that existential crisis kind of way, like, “What’s wrong with me?” Some people meet two people, and they get married. And I’m meeting hundreds of people, and I don’t know if he’s right yet. It’s kind of scary.

DS: What attributes are you most looking for in a man? Your ideal situation?

LL: I think I probably want what a lot of other people want, which is somebody who’s kind, loving…somebody who’s a mensch, who can talk to other people. I’m social, and I like going out and hanging out with friends. I want somebody who’s part of the gang, who can hang out and joke around. Somebody intelligent – maybe not necessarily super book-smart. They don’t have to have a perfect body, but they’ve got to be energetic and healthy enough to take some walks and hikes. Somebody who can be a good friend, and somebody I feel like making out with.

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