From dating horror stories to their own attempts at matchmaking, cast members from The Matchmaker weigh in on their memorable romantic experiences below!

KRISTINE NIELSEN (Dolly Gallagher Levi)

What were your best and worst dates?
The best date was one I went on with my husband. We always go back to a restaurant in Louisville when we visit my in-laws because of that magic moment when we met. The worst date was probably a tea dance my mother insisted I attend in Annapolis where young girls were arranged to meet the midshipmen. The girls were lined up behind a curtain and whoever came out from behind it was then their date for the day. I had nothing in common with the man to whom I was paired. The pairings were really all just based on height. It was an excruciating day.

What’s the best romantic advice you’ve received or that you tell others?
“Never go to bed angry.” You have to talk it out; honesty is always the best policy. If you sleep on something, you hide something. It’s always best to get it all out there.

If you could go on a date with anyone (living or dead), whom would you choose?
I’ve always been obsessed with Marlon Brando. When I was a young girl I had an assignment in home economics class for which we had to put together our “dream house.” I cut up a bunch of pictures from my mother’s Architectural Digest and wrote that I wanted to live with Marlon Brando and all his illegitimate children. The teacher was worried and called my mother saying, “She’s crazy! She wants to make a home with this lewd, horrible man!” My mother had to explain that I didn’t even know what an illegitimate child was and just loved a movie star!

THEO ALLYN (Ermengarde)

Would you be a good matchmaker?
I would be a dreadful matchmaker. I would take it way too personally and be heartsick if a couple I set up fell apart. I would blame myself for getting it wrong and causing them pain. I don’t want that responsibility!

What were your best or worst dates?
The worst date I ever had was with a guy I met through an online dating service. He took me to a baseball game for which he had standing room only tickets. So we stood at the baseball game for hours, not really talking, and taking turns fighting the crowd to buy beer. I was profoundly broke at the time, so while I wanted to be independent and autonomous, I couldn’t believe I was buying so much overpriced stadium beer. Then I never heard from him again.

If you could go on a date with anyone (living or dead), whom would you choose?
Paul Newman. Or Idris Elba. Or both, I guess, if this is a wish list.

What’s the best romantic advice you’ve received or that you tell others?
It’s cliché, but honestly, the advice I give myself is that I have to like who I am; I have to want to be with myself. If I’m going to have any kind of meaningful relationship, I have to have a healthy one with myself. Also I have to love the person I’m with for who they are, not who I hope they’ll turn out to be.

Kristine Nielsen and Theo Allyn in rehearsal for The Matchmaker. Photo by Liz Lauren.
Kristine Nielsen and Theo Allyn in rehearsal for The Matchmaker. Photo by Liz Lauren.

SYDNEY GERMAINE (Minnie Fay)

Would you be a good matchmaker?
My expertise is in the area of helping existing couples maintain healthy relationships rather than creating new couples. I enjoy playing the role of the mediator between partners or with the person who really needs to vent about something in their relationship. I personally wouldn’t be interested in being set up by someone else, so I don’t have interest in setting up others. If you want someone, I say go after that person on your own terms with politeness and consent.

What were your best or worst dates?
I’m thankful that I actually have a history of really good dates. My ideal date would be something involving really good food. I was voted employee of the month at the restaurant where I work and received free dinner and drinks for the prize, so my significant other and I had a feast that night and then slept in the next day. It was the best. Seeing a play is part of a great date, too.

If you could go on a date with anyone (living or dead), whom would you choose?
I would really like to have a large dinner party date with a collective of other [transgender] actors, directors and producers — some names include Rhys Ernst, Laverne Cox, Alexandra Billings, Tom Phelan and Mya Taylor. A lot of us aren’t [consistently working] in the theater and film industries, or it’s just plain hard to find others, and I’d love to be able to meet and eat with others like myself and hear more about how they are successfully doing what I’m trying to do in my own career.

What’s the best romantic advice you’ve received or that you tell others?
The best relationship advice I’ve ever been given, and what I’ve in turn said to others, is, “Trust your gut.” I wasn’t good at listening to this for a bit. You usually know if a relationship is right for you or not; you usually know when it’s time to go, but a lot can get in the way of making the best decisions for yourself. Trusting your gut, to me, means regularly checking in with yourself to see if your needs are being met — emotionally, sexually, socially and professionally. It’s important to ensure you’re in a situation where you’re not being taken advantage of or sacrificing yourself. Sometimes the metaphorical heart and brain get in the way of things, but the gut knows what’s up. Trust me.

ELIZABETH LEDO (Irene Molloy)

Would you be a good matchmaker?
I am not sure if I would be very good at being a matchmaker. My weakness lies in my tendency to give people the benefit of the doubt, so I could possibly get myself in a bit of trouble by overlooking some important faults in someone and linking them up with someone else who is not interested in navigating said overlooked faults. I have, however, created situations that brought two people together who ended up becoming a couple without that having been the actual intention.

How would you describe your ideal date night?
It would be very simple: a good meal, some good laughs and a desire for the night to continue.

If you could go on a date with anyone (living or dead), whom would you choose?
I have wanted to go on a date with Bernadette Peters since I was 16 years old. That hasn’t changed and the reasons for wanting to do so are endless!

What’s the best romantic advice you’ve received or that you tell others?
The best relationship advice I have ever received, and the advice I give as well, is to remember to communicate. I see so many relationships fracture simply because the two people are not being open with one another.

POSTELL PRINGLE (Cornelius Hackl)

Would you be a good matchmaker?
I’d be a terrible matchmaker. I clearly learned nothing from years of watching The Love Connection every evening with my dad. That being said, I’ve had my hand in connecting people a lot. I make an impeccable wingman at a bar for male and female friends alike. My friends have gone on to make all sorts of connections based on my efforts, though I’m not sure if “love” was the resulting connection.

Have you ever been set up by anybody, and if so, how did it go?
I was set up a few times. Every occasion resulted in a great night…for me! I can’t say the same for my dates.

If you could go on a date with anyone (living or dead), whom would you choose?
Sade Adu [the singer known as Sade].

What’s the best romantic advice you’ve received or that you tell others?
The best dating advice I’ve ever been given is “Ro-mance without fi-nance is a nui-sance.” The relationship advice I’d give to someone else is “Happy wife equals happy life.”

ALLEN GILMORE (Horace Vandergelder)

Would you be a good matchmaker?
I have done some matchmaking without knowing I had done it! But no, I don’t think I would make a good matchmaker. I’m interested in people individually – not so much as pairs.

What were your best or worst dates?
Best or worst dates are all about the company, I believe. The best date I remember involved great conversations while walking all around lower Manhattan on a beautiful spring afternoon.

If you could go on a date with anyone (living or dead), whom would you choose?
Going out with Elizabeth Taylor would have been a great date. She seemed so funny, warm and intelligent, but very down to earth.

What’s the best romantic advice you’ve received or that you tell others?
If I had great relationship advice, I probably wouldn’t be single now!