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Male Mind: John, The Boundless Bachelor

Welcome to Male Mind — The interview series featuring a different man’s take on love-life topics every month. From dropping the right cues to making the first move, Evyenia Trembois gets the inside story straight from the source.


E: What are you using right now to meet women?

J: I’m on The League and I’m on Tinder.

E: Tell me about your last online date.

J: I met this woman from The League. She was very nice, we had a nice time. I realized she was using pictures from five or six years prior. I felt like that was a little bit disrespectful when I got home, and I didn’t want to go out with her again. We didn’t have a deep connection, I wasn’t feeling it

E: Why did you feel disrespected?

J: Because I’m busy. And it’s dating. There’s someone for everybody, you just need to be honest about what you look like. All of my pictures are within the last 12 months because every two to three years, how you look changes a little bit.

“I think it’s important to be honest about what you look like for the purposes of dating.”

E: Do you often find, with online dates, that people don’t look as you expect them to?

J: I don’t often find that because I like to think that I am pretty attuned to the different tricks people use to manipulate their looks for photos. Being a production professional, I kind of know a little bit of the different tactics that are out there. So I generally find that people look like their pictures, but I’m very selective about who I’ll go out with because I can tell when someone’s being a little bit smooth with their photos.

E: What’s your go-to for an online date?

J: Drinks. Just drinks, yeah, because you don’t know anything about the person, generally speaking. There was a time in online dating where people used to exchange emails and build up a little bit of romance before they met, and you would even maybe try to do something fun for a first date, but I think… 

“In today’s dating culture, the stakes are just too high and the time too limited, especially for someone like myself who’s just super, super busy.”

So I want to get out, see what the person is like in-person, see if they can hold a good conversation, learn more about them and what they’re like. I like to think I’m a good conversationalist, so drinks are a good way to do that.

E: How do you feel about footing the bill on a first date?

“I always pay 100% of the time.”

E: Do you ever feel frustrated about that? Do you ever not want to pay for the date when you’re not interested?

J: Nope, I always pay. I’m never interested, but I always pay. (laughs)

E: Do you meet women in-person?

J: I have. I do. Yes.

E: Tell me about the last time you met someone in real life.

J: Last night. That’s very rare though because there seems to be bad vibes in the air right now about being forward romantically, so I’m reluctant. Also, I meet women through work, (not that they work for me or with me), but that we’re all in the same industry, so I’m hesitant. I think it’s best to wait until the woman drops a cue, otherwise you create tension (which, for me, could leak into professional life).

E: So, if you, for example, saw a girl that you found attractive in a coffee shop, would you approach her?

J: No, never. I think it’s disrespectful in a certain way because I can imagine what it must be like…men are the traditional pursuers in dating, and some are too aggressive. The women I’m typically attracted to likely already have enough unwanted attention to deal with. So I feel it’s disrespectful. 

“Just because I like the way someone looks, doesn’t mean I should invade their space and force them to deal with me.” 

You know nothing about that person…it’s just not something I’ve ever liked to do. If I start talking to someone organically, and it somehow evolves into a long conversation, and I feel like they’re enjoying themselves, then I might ask if they want to get a coffee or have a drink. Or, I might see someone and compliment them on their jacket (or something they’re wearing), and see if they either say thank you and move on, or if they take that and try to keep the conversation going.

“But I never just walk up to a woman on the street and say Hey, I think you’re gorgeous, would you like to get a drink with me sometime? I know men who do that, and there’s nothing wrong with it, I just don’t feel comfortable putting that on someone.”

E: Are there any cues a woman could drop that indicate she wants you to approach? And would you feel comfortable with a woman approaching you?

J: The ‘on the street’ pick-up is hard. But, I’m totally open to it. Sometimes women start talking to me on the street…the other day I was at a coffee shop and this woman started talking to me about my dog. We kept talking, and I was wondering, does this woman want me to ask her out? She was very cute, I thought she was attractive, but I didn’t know!

She was about five or six years younger than me, if not more. I thought, maybe she’s just being nice…I think she’s attractive, but who knows what she thinks of me. Maybe she’s just having a chat.’ So I didn’t ask her out.

“I want to be able to have a nice chat with someone who happens to be good looking without trying to get them to go out with me.” 

It ruins the serendipity of life if with every interaction you’re wondering if someone’s trying to date you. So usually I’ll wait for a woman to ask me something…there are certain things a woman can drop into a conversation that lets you know they are interested in going out with you. Questions like, do you live in the neighborhood? Or, do you come here a lot? Whatever… 

“Any personal inquiry about your daily routine is a cue.” 

Also, personal questions like where you live. These type of questions hint that they want to get to know you better, versus just a random chat on the street.

Evyenia insight: As a single, relatively ‘conventionally attractive’ woman, I found all of this refreshing, and frustrating at once. Any time a man approaches me, I tend to think they’re hitting on me (but it’s never the ones I’d like to approach that do), so it’s nice to think that there are guys like John out there. That said, it’s interesting to hear that there are little tricks we can pick up on, or plug into conversation to show interest.

E: You mentioned age earlier. You’re 38, never been married. No kids. How does that play into dating for you? And what are you looking for right now?

J: I want to find something serious, you know. I want to have a shared household with somebody that is going to be a long-term, marriage oriented relationship. That’s what I want, that’s my goal.  

“Dating is no fun in Los Angeles, that’s for sure. And the older you get, the less options there are.” 

The older people get, the more likely they are to be married, so the pool is smaller.  And then, you know, most people don’t get more attractive after their late thirties. So between all those things, I feel a little bit of time pressure. 

E: Leave me with a funny date story!

J: I went on this date with this woman from the internet a couple of months ago, and she showed up to the date super nervous. Regardless, we tried to have a conversation that was super stilted and awkward, and then after fifteen minutes — like we hadn’t even finished a drink — she got up and was like ‘I just met someone last week who I’m really into so, I gotta go!’ And she just walked out. I was like…great!

This interview was edited to omit certain questions on 5/8/18 as requested by the interviewee. While it’s very important to us to be honest and unfiltered with our content, it’s equally important to respect the privacy and wishes of those we speak to. Thank you John for talking to us, we appreciate you! 

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