Get to know Diggy Moreland

All week, we have been revealing hints about The Jam's Mystery Man!

He has been revealed, and it is Diggy Moreland. Look familiar? Well, he was a former contestant on televisions programs The Bachelorette and Bachelor in Paradise!

Since he did not leave those shows with the love of his life, he is still searching — and now you have the chance to win his heart. All you have to do is submit a video here. But first, learn a little more about Diggy in this interview. 

What are the 3 top things that you look for in a woman?

Diggy: She has to have a sense of humor, she has to be down to earth, and she has to be spontaneous.

How spontaneous?

Diggy: I am talking spontaneous like… I wouldn't like somebody who has to plan everything out. I am like, "Let's go out," and "Let's have fun today." I feel like those are the time you have the best fun with somebody. Someone who is not by the book all the time, someone who knows how to let loose, have fun and can just go with the flow.

So if you go on a trip, you don’t want an itinerary?

Diggy: NO. [Laughs] I want to wake up and say, "What do we feel like doing today?" I am fine with a little structure, but just a little.

How important is it for you to share the same interests?

Diggy: I like to have some common interests, but I do like to learn new things. I am all for new things and having new experiences. If there is something she likes to do — such as ballroom dancing — I have never done that before, never had a desire to do that before. But, if it is something she loves, I will try it.

What would be the perfect date?

Diggy: Are we talking Chicago in February? [Laughs] A great date would be dinner and get a chance to have some great conversation. I am not a foodie by any means, but I do like to try new things. I think it would be cool to do a tour. It will be February, so we do not have to do a double-decker bus or anything. Maybe a carriage ride. We could get a chance to admire the architecture and enjoy the scenery.

Favorite things to do around town? 

Diggy: I love to shop so I love going to Michigan Avenue. I am a big pizza guy, so I like Giordano’s. I also like riding my bike, whether that is on the lakefront path or just in the neighborhood. I also like to read and check out different coffee shops. I like sneakers so I don’t mind venturing around the city to different sneaker shops.

What are the physical characteristics you look for?

Diggy: I love a good smile. I pick up on teeth very quickly. This is a sidebar — but if you all can find someone with freckles. Freckles are super attractive.

So real freckles, not the new stick-on ones?

[Laughs] Well, I prefer natural. You have to be consistent. If you stick them on, you have to keep it up for the next 30 years or so. The other thing would be, someone who takes care of themselves, and in good shape. I like curly hair, but it is not a deal breaker.

Any dealbreakers?

Diggy: Smokers. I can't date anyone who smokes.


Inside date or outside date?

Diggy: Outside date. We can bike ride, walk or anything outside.

Morning brunch or evening rooftop drinks?

Diggy: This is a tough one, but rooftop drinks. My favorite spot is J. Parker.

Lou Malnati's or Giordano's?

Diggy: Giordano’s! I live next door to a Lou Malnati’s but still like Giordano’s. I can’t get with the crust. I don’t like deep dish pizza, though.

Cubs or White Sox?

Diggy: Cubs. I will not go to White Sox stadium. The only way I will go there if is they are playing the Cubs.

Chicago Athletes: Dwyane Wade or D. Rose?

Diggy: Dwyane Wade, only because I played against him in high school. He was a senior and I was a freshman. So, I will pick him because of that connection. However, I do have a soft spot for Derrick Rose.

Any final things you want to share about your dream girl?

Diggy: She has to be down to have fun. I am very goofy and rarely serious. I am looking for someone to match that.