If there is one thing about Lisa Loeb I took away from our interview, it's this: she really, really likes to hook people up. I wouldn't be surprised if in an earlier life she was a village matchmaker somewhere in Eastern Europe. She'll definitely make a great bubbe someday, albeit one with a funky pair of glasses.

Anyway, in Part 1 of this interview, Lisa and I talked about her new show on E!, #1 Single, talking to Howard Stern, and a little about eggs and cheese. Today, things start to get a little odd. I don't know what prompted Lisa to turn the tables on me; it could have been a little bit of boredom, burnout from publicity overload, or she was truly interested in my singlehood. It doesn't matter. Let's just say that about halfway though the interview, things started to get really interesting.

But first, a little discussion about eyewear:

[Photo: Kevin Westenberg]

Joel Keller: Did you ever think that when you do this type of stuff that you should put on a pair of contacts and just go out like that?

Lisa Loeb: I did in college, actually.  I used to be in a popular band in my college; people would write us fan letters.  Every once in a while I'd put on contacts. We had a dance -- I took a lot of dance class in college -- and we had a final exam, which was a final performance out in the middle of campus, like outside.  And I just didn't really want people to look at me, I just wanted to be part of the group and not stand out. So I didn't wear my glasses, because people also recognized me for my glasses in college.  And I wore my contact lenses for the dance thing; not even friends recognized me, which was awesome.

But I've gotten more and more allergic to contact lenses; I was allergic to them in high school. So I only them wear them once, twice a year, maybe if that.  But I get these little blisters in my eyelids, so I don't really get to do that so much. And when I'm not wearing glasses, I can't really see anything.

JK: I completely sympathize, Lisa, because I'm a long, long time glasses-wearer.

LL: So you know.

JK: Yeah I try buying contacts, but I never wear them, so...

(Writer's Note: Here's where it takes a bit of a turn... I was taken aback by this, to say the least, so I was stammering a little more than I'm letting on in the text.)

LL: How do you meet people, like, for dates and stuff like that?

JK: You know, I do some online stuff...

LL: A lot of my friends do too, actually.

JK: I used to do that a lot more a couple of years ago, and I just... not that I had awful experiences, Lisa, but it was just... they were just... they were just not... they were not good, because online's really tough, you know what I mean?

LL: I also heard recently they started pooling a lot of the online dating services, so the pool of dating is the same and you have to pay different levels of money for different levels of accessibility to that dating pool.

JK: Depends on the site I think.  I used the Nerve personals a lot.

LL: Yeah, I have a friend who used that too...

JK: You know why? It's funny because the Nerve personals have a lot of people that are kind of your stripe on there, you know, creative, umm...

LL: You know where you should go?  I was just talking about this with a friend of mine who's a professional, she's got a TV show about knitting, and she writes articles for newspapers and stuff. All over the country there are women who knit, and they go to these knitting circles and knitting stores. Some of them are just interesting and cool and crafty and they're just all hanging out. It's not like they're all dressed up at a bar; it's quiet, you know, like people are just sitting around drinking coffee doing cool knitting things, and cool sort of younger people in their 20s, 30s, 40s, they all sit around and hang out and knit.  And there's barely any men there, so the ratio is much better for guys.

JK: Which helps.

LL: And its fun, though, because it's not like you're meeting people who are trying to... like a bunch of drunk people in push-up bras... maybe they have push-up bras on, but they're just being themselves, which I think is the best thing when you're seriously looking for someone that you actually want to have a relationship with.

JK: I can tell that's the direction that you want to go in...

LL: Yeah, it is.

JK: You don't want to just meet someone at a bar.

LL: Not really...  Although you never know who's going to be wherever.  I mean, I used to meet people at bars when I was in... no, I used to DJ when I was in high school, I'd DJ parties. So when I go to a bar, still being a musician, I'm paying more attention to the people who work there, the people sort of behind the scenes at the bar. Because I'm used to being the person who's playing in the band, or friends of the sound engineer at the bar, or friends with the guy who owns the bar, and less friends with the people that drink.  But you have to find the right bars to go to, where it's where your peers hang out.

JK: I tend to a lot of stuff like... um... you know, I'm in writer's groups... like I'm in a writer's group that's just about all women...

LL: Oh, that's cool!

JK: Yeah. Of course, most of them are married, but you know, hey they have women friends, though...

LL: But do they know that you're single and you're looking?  Because they sometimes have friends or friends who are divorced, and that's also a really good prospect at this age.

JK: That's true.  That's what I'm trying to do more, is meet people where I like to be.

LL: Exactly. That's a good thing.

JK: And you're trying to do that too.

LL: Yeah, well, I like bookstores, but... In LA there's some cool places... There's a place that's a record store called... Amoeba Records (Writer's note: it's actually Amoeba Music)... there's just tons of cool people there looking for records. It's not like people who are really, really normal and average looking for normal, average records. It's also not people who are totally whacked out looking at a really alternative record store.  It's just interesting people looking for records.  And there's a huge store, and you just start conversations over albums you're interested in -- or movies; they have movies there too that you can rent.

JK: So you've done that kind of stuff?

LL Yeah, you just walk around, sometimes people play, like in-store; Aimee Mann played there. But it's daylight; the lights are on in the store, you can actually see who else is there, you can start up a conversation with somebody.

JK: I've tried that at Barnes and Noble, I think...

LL: Well, for book readings it's OK, because people are there sitting, watching.

JK: Yeah, for readings, it's OK.  Not just while someone's cruising the magazine rack.

LL: Yeah, then they're like [gruff voice] "Why are you looking over my shoulder?", and you're like, "Oh, no sorry I didn't mean to see you read that book!" [giggles].

JK: That's the problem with the bookstore.  People are very quiet and to themselves.

LL: Barbecue stores are good!

JK: [suprised] Barbecue stores?

LL: [giggles] You know, where you buy barbecues and stuff like that?

JK: I'll have to look.

LL: It's good for girls because they have guyish guys there looking for barbecues.

JK: I'd have to figure out where to put it, since I live in an apartment with no terrace.

LL: Yeah, that wouldn't work.

(Writer's Note: Here's where I try to wrench things back to something resembling an interview)

JK: How did you figure all this stuff out, Lisa?

LL: I talk to friends, and I've met people at different places. I'm also like my mom, and I can talk to whoever without a problem.

JK: You ever think about getting into the dating advice biz?

LL: Ohhh... Actually. if you listen to the E! Entertainment website, I have a little podcast where people write in and ask questions.  And I'm like "Well, I'm not sure about this but..." and I'm like [voice goes high] "blah, blah, blah, blah," and I go on and on.

JK: How much of this advice are you taking yourself?

LL: I'm taking as much of it as I can. I think the hardest advice to take is... it's something I think I have to learn through experience.  Some people say I need to move on more quickly after I meet somebody, to trust my instincts and not go on a second or third date. Other people say I need to go on more dates and give people more of a chance because you might not know at first.  So I'm trying to balance that out, and it's a hard thing to do when you're a busy person.

JK: Are you one of those type of people who are "one date and out" or do you give people more of a chance?

LL: I give people more of a chance.  It's a little complicated when the schedule's busy. But there are just so many different things to find out about people, and I just like talking to people. I just feel like that's one of the reasons we live on earth. It's interesting to realize how small the world is and how you relate to different people and what's going on in their lives, and your life, and everything.  Also, when you work a lot, and you're actually out in public talking to people, you're like, "Oh, wow, there's people out here!" You feel like you're coming out of that bomb shelter or something. But I think it's important to start discerning when there's more attraction and when there's not. It can be confusing.

JK: Well, it's confusing on both sides. There's different issues on the men's side than on the woman's side.

LL: They're what, do you think?

JK: Well.. I have a friend who has a blog, and his big beef is that men should no longer pay for dates. That kind of thing.  Because women have their own jobs their own careers... he does contend that women should ask more men out.

LL: I think women should ask men out if they want, but here's the deal: I also have a problem with learning how to let the guy pay for me, 'cause well, it should be even, you know? I work, why should they have to pay?  If I'm already dating somebody, and I really want to go on an expensive vacation or to a restaurant that they might not be able to afford, I think the person who invites (a person) to the more expensive place should chip in more for it or be more responsible for it.

But if you're dating seriously, and you want to have kids... this sounds really weird and prehistoric... not really prehistoric, but you know, some kind of step in evolution... you want to know that the person that you're dating, if you end up marrying them -- even if it's a first date -- if you end up marrying them they're gonna be able to take care of you in some way.  I don't mean that the relationship isn't equal, but if you decide to have kids, you will be taking care of the kid more, especially when they're a baby, and you have to know that the guy can kind of help provide.  In the end, I think the relationship should balance itself out and different people have diffrerent responsibilities. And maybe they have equal financial responsibilities, or maybe the woman might have more financial responsibility, but the guy might have a different type of responsibility.  It evens out in some way.  But I think it's important... 'cause I've also been in relationships where the guy didn't pay, or wouldn't pay, or couldn't pay, and... I feel like it can throw the balance off.  'Cause in the end the guy's gonna want to feel guyish, like he's sort of in charge, and when the woman pays or opens the door and does all this stuff, somehow -- even though it's really old-timey -- somehow it throws the relationship out of balance.

JK: For some guys. I mean, I don't get hung up on all that stuff, to be honest with you. 

LL: Yeah, but like the woman... yeah, it's true.. I mean, I'm still trying to figure it all out, but it's an issue for me, because I'm like... well, I can take care of myself, and support myself, and I have a house, you know. I'm fine, I don't need a guy to pay for me; let's just be in an equal relationship or whatever.  But, you know, on the other hand, there's something symbolic about the guy being able to be in charge in some way... like you have to let him be in charge [laughs].

JK: [also laughing] Well, it's good to know you like to take charge at certain points...

LL: Well, I think it can be a shared responsibility.

JK: But to me, and this could be complete BS, but I'm probably one of the few guys who think it should be an equal partnership and not one person lording it over somebody else...

LL: Right. The woman does need to feel like she's being pursued, though. Like the woman can't pursue the guy just because she'll always feel like she doesn't trust the guy. I know that sounds weird again and it's really old-timey, but I've seen it over and over and over again in relationships.  There's some kind of tricking the guy into the relationship and then she never trusts that he likes her, because she tricked him in the first place.

There's a great book called If the Buddha Dated by Charlotte Kasl. She tends towards the equal relationship; she's really great at explaining the whole thing.  She's my main dating guru.

JK: I'll have to look that up.

LL: Yeah, it's really great.

JK: You ever try eHarmony?

LL: I want to! It looks so scientific on TV, doesn't it? I just have a problem, though; I was going to go on JDate because, well, there's a lot of interesting people, you never know who you're going to meet. And then, um, I just didn't feel like putting my income, or my picture, or my job, or a lot of information about myself [laughs], and after a while, you end up with a not very interesting profile.

JK: How is this show put together?  You know how a lot of reality shows twist the reality quite a bit?

LL: I was really involved in the post-production of the show, because I really wanted to make sure it was represented properly.

JK:  Maybe not on dates, but how about in scenes where, like I saw your sister (Debbie) out pounding the pavement for you...

LL: Well, that was a fun thing; she's wanted to do that.  She's pretty outrageous, my sister.

JK: Yeah, I can tell that from the show. But did the dates just play out the way they played out? There was no prompting by a writer or director?

LL: Yeah, they did. They just played out.

JK: OK, the big question is: have you found someone from this whole process?

LL: I can't tell you that!

JK: Well, I had to ask...

(UPDATE: Listen to clips of the interview on our weekly podcast!)