On Wednesday, May 15, The Great Love Debate arrives at Boston’s City Winery for wine-fueled conversation about everyone’s favorite (or least favorite) topic: romance. At these internationally touring shows, audience members sip and vent in a town hall-style forum helmed by dating expert and charismatic romance maven Brian Howie (yes, he’s Jewish!), billed as America’s No. 1 dating enthusiast. (He tells me that he’s very happy with his love life.) He aims to answer the question: Why is everyone still single? And, of course, audience members have plenty of opinions, though he says that many people end up pairing off after his shows.

He’s always joined by local voices; on Wednesday, dating coach and millennial love expert Samantha Burns will also appear. We talked to both about how to find true love, or at least a decent date.

What’s the dating scene in Boston like?

Brian Howie: There’s a good balance of people who are serious about their career, yet will still have fun. They’re not one or another, they’re not like, “I need to wait till I get to a certain place before I either date or have fun.” And they’re not too, “I’m just gonna goof around,” because it’s too expensive for them. … But I would say of the Boston, Massachusetts, desirable dating pool, at least the ones who are probably reading you and want to know, less than half are probably from Boston, and a lot of people look at Boston as a stepping stone to somewhere else.

Right. So, some transients in here!

Right, “I’m gonna go to Boston until I get to New York,” or, “I’m gonna go to Boston until I get to London or D.C.” So they’re not 100% diving in and putting all their chips on the table, because they’re not gonna necessarily stick around.

Do various cities approach dating differently?

BH: New York, and a little bit Boston and D.C., are more heavily Jewish cities. They’re a little bit more, “Listen, I’m open to everything, but my mother will get really mad at me, so I’m only dating somebody Jewish.”

Might that limit you a bit?

BH: I think it’s limiting. I don’t question somebody’s [religion] or how important it is to them. But if you’re trying to match up, “Here is where I am in my relationship with God or my religion,” and I’m trying to match that up with somebody who’s exactly the same at this moment, it’s like trying to hit two bullseyes. It’s like trying to hit a moving train because people’s religious situation is based on how often they go to temple or how often they go to church. It changes with life. So you’re basically saying, “I need to be matched on this one three- or four-hour point every week.” I think that’s a mistake. … You know, before you get into how you want to raise your kids, which is a different discussion, I think just in terms of dating, you need to be open to everything.

What’s the biggest mistake men make in approaching dating? And what’s the biggest mistake women make? Where do they differ? What do women do wrong, and what do men do wrong?

I would say that women look for red flags, and men look for green lights. And that’s a mistake by both, because sometimes men, if they’re only looking for green lights, they might be overlooking signals where a woman might be uncomfortable or not reacting or not getting the same reaction they want. On the other hand, if a woman is just constantly looking for red flags, it’s a negative way to go into dating. It’s not only fear-based, it’s just a pessimistic way to do it: “OK, I’ve seen the good, where can I find the bad?” That’s a mistake.

They’re expecting the worst, in other words. They’re waiting for the other shoe to drop?

BH: Right, so now matter how good it is, the less they trust it. We’ve got a lot of guys coming to our show, and they’re like, “I don’t understand. I’m a good guy, I’m a nice guy, and she keeps going out with the bad guy.” And I’m always like, “With the bad guy, she’s like, ‘OK, I see what I have to work with. Let me figure out if I can get to the good here.'” With a good guy, they don’t trust what they can’t see, but they assume it’s there. It makes it hard.

So, for people who are coming to this show in Boston, what should we expect? What should we do? Should we bring our questions? Are we going to meet the love of our life?

BH: Probably. Forty-eight couples that we know of have gotten engaged after first meeting at one of these shows. And that doesn’t even count the hundreds and hundreds who exchange their mindset, or their thinking, or their fears. … There’s very active congregating, and communicating, and adding a little wine goes really, really far. People come to our shows thinking, “I think I’m the only one who feels this way.” And they leave knowing everybody feels this way, and the fear goes away.

Everybody feels what? Lonely? Alienated?

BH: They feel like, “There’s something wrong with me.” Especially the women. Once women realize it’s not so easy for the men, they really like that. And vice versa. The men are afraid of being rejected, and the women are afraid of being hurt. Having a conversation about that really goes a long way. … The very first question we ask is, “What’s the biggest challenge with love, dating and relationships in Boston in 2019?” And one hand goes up, and we go from there. And it can go in all kinds of directions. It’s sometimes women against men; it’s sometimes women against women.

Let’s talk a little bit about the dating mistakes you see people making, Samantha.

Samantha Burns: The biggest one I see everyone making is the grass-is-greener mentality, especially with online dating and how much technology has impacted our dating choices. Everyone thinks there is this next best thing out there, bigger, better, faster, stronger, and they’re hesitant to commit to one person. Or they see one or two little things that shouldn’t ultimately be deal-breakers, but because they have this wealth of other potential options, they just don’t pursue one person and they keep dating and going on first dates.

What do single people want? Do they want to just date a lot or do you think all people are looking for forever?

SB: I think it slightly depends on age, but we do have research. Match has data that says the majority of singles out there are looking for a serious committed relationship, and they’re looking for love. And we also know, though, that online dating is now the most popular way singles meet, and the average user is on three apps. We know that millennials especially are feeling really lonely, and finding that technology is actually making it more difficult to find love … because of this grass-is-greener mentality. We know that the online dating swiping apps activate the reward center of your brain and can actually be a bit addicting, because you get that dopamine rush every time you match with someone. So we start coming back to that app just to see who we can match with and if that person likes us back, but we don’t necessarily have the intention to get offline and meet in person.

What’s your advice to people who are in this cycle of swiping? What can people do in this day and age to actually find a lasting relationship?

SB: My rule to help clear out the dating clutter is that you have to be an intentional swiper. You have to agree with yourself to message every person that you swipe right on or that you match. That way, if you’re committed to at least messaging someone, you won’t just be swiping for the sake of swiping; you’ll be swiping to set up a conversation. And then, of course, in the conversation, if you like 80% of the things you’re talking about, and 80% of someone’s profile, go out and meet in person, because it’s the only way to see if there’s real chemistry. I actually met my husband online. I met him on JDate!

What if you want to get married and have kids, and it’s not happening for you? Maybe you’re getting older and you meet somebody. They’re nice and you’re compatible, but there’s no spark. Should you hold out for the spark, or is sometimes “nice enough” enough?

SB: I think that “spark” isn’t quite the right word, because I really caution people actually away from looking for that intense spark or chemistry. Chemistry is a good thing, and you absolutely need physical attraction, but I think the spark is lust. Lust is a bunch of neuro-chemicals going around in your brain as a love potion that makes you excited and giddy and attached to someone. But what we see is this: The honeymoon phase eventually wears off, and then you’re stuck with who this person is underneath all of that attraction. And a lot of times, you can be blinded by love, and we know through neuroscience that the parts of your brain that make rational decisions and judgments actually shut down when you’re newly in love. So we’re not even making the best choices for ourselves. So I wouldn’t make your choices by lust. … So I think for women who are getting older and really wanting marriage and kids, to some extent I would say see if love naturally develops and grows—or I should say see if attraction also develops and grows, especially for women.

Is the ultimate goal to get married? Is it to find love?

BH: If you gave people a roadmap to a happy, loving, sharing, honest, sexually active, growing relationship with just one other person, how many people would sign up for that? They all would sign up for that; they just can’t see the road. So, ultimately, everybody wants the same thing, even people who are just like, “I’m not looking for anything serious.” Those people are either afraid that it doesn’t exist, afraid it’s gonna be too painful or they don’t understand how to get there. But, you know, we’re selling hope at these shows, and that goes a long, long way.

Sound promising? Get tickets here.