Interview with a Single Guy

Below is what happens after I throw a house party, drink too much whiskey and discuss dating and relationships with a single man that I just met. That lovely guy, John, a friend of a friend (and now a friend of mine) agreed to answer some intimate questions about his love life to help us all better understand the mind of a single man.


Name: John

Height: 6' 0"

Age: 34

Occupation: Non-profit, I manage a program for kids with autism 

Relationship Status: Single

How long have lived in NYC? 7 years

Let's cut to the chase. You seem like a good guy. Why are you single?

I am very picky (to a fault), also I don't really want to be in relationship, it has never been a goal of mine.  I see so many people in terrible relationships, I would rather just hang out with my friends, and occasionally date girls that I am interested in. I am sure you have heard a lot of people throw around the idea that single guys my age, especially in New York, are totally jaded. Well, I am a perfect example of that. Sad but true. 

How do you usually meet women? 

Usually through friends, though I also have the bad habit of dating girls from work.

How you ever done online dating? Which sites? How do you feel about it?  

I have tried Okcupid, however I've always been really leery about online dating. It just seems slightly unnatural to me. Call me old-fashioned. 

Ok, Mr. Old Fashioned. Do you ever talk to women you don't know at bars? What do you say to initiate conversation? 

I do occasionally, however, having the guts to initiate a conversation with a random girl I don't know is one of my main weaknesses. Once the conversation has started I'm a total charmer and it usually goes really well (does that sound arrogant? ha), but I just feel that there is often no good non-awkward opening line to initiate the conversation.

How often do you go on dates? 

Very sporadically, actually.  But if I had to try to guess at an average, maybe a few times a month? 

Do you normally ask out women via text or another way? 

I'm not going to lie, I often do so via text. However, that is just because I do everything via text. I hate talking on the phone. I haven't talked on the phone since the '90s, (he laughs).  I would ask a girl out in person, but not if other people are around (which they often are, if you don't really know the girl that well yet), that is just awkward.

Do men over analyze texts - the words and the response time - as much as women do? Because we do it a lot, and we get help from our girlfriends. 

I don't think that men over analyze texts the way that I know women do.  I know that I don't over analyze them, and I'm an over analyzer generally.

If a guy responds to a woman's text message 12 hours or more later, can she assume that he's "just not that into her?" 
No, people are just busy, especially in New York. I try not to text much if I'm out with friends because I think it's rude...though it's really difficult for me, because I'm a total texting addict, so I don't think a girl should ever assume that. 

Who pays on the first date? What about the second date? 

This totally depends on the two people. If I really like a girl, I will usually pay on the first date.  However, and I'm just going to say it, it's 2012 and I don't think it should be expected that the guy always pays, I respect a girl more when she offers to pay for what she had, and I feel that should almost definitely happen by the second date.

If you really like a girl after the first date do you initiate contact? How soon after the date? 

Yes, I will initiate contact, how quickly afterward really depends on the girl and how the date went.  In this age of texting, I have actually texted a girl later the same night, especially if I get the impression that the girl liked me too. More often than this looking "too eager", girls tend to actually like it/think it's sweet, again....especially if they were into me too. 

What was the longest relationship you've had? 

Umm....8-9 months. I was hoping you wouldn't ask this question. Again.....I'm totally jaded.

Haha. Well now I have to follow up with...have you ever been in love?
I doubt it.  

What type of relationship are you looking for right now? 

I am not looking for a relationship at all right now, except maybe a casual one.  I recently met this girl who I really like though, and the way I feel about her is kind of changing my mind about a lot of things. She is the first girl in a loooong time who I would even consider dating exclusively. However, I am not sure it will really go anywhere.  

Why don't you think it will work out with her? Are you just protecting yourself and expecting the worst outcome?

I am just expecting the worst outcome, Yes. I wouldn't say I'm protecting myself though, i am just a pessimist in general. I met her at work, but we don't work at the same office.

Chivalry. Us ladies often throw this word around. What does it mean to you and do you think it has any place in dating today? 

I do believe that chivalry does have a place in dating today. When I really like a girl, I become very chivalrous without even making a conscious decision to be.  To me, chivalry really boils down to treating a girl with the utmost respect, trying to make her as comfortable as possible in any situation, both emotionally and physically. It isn't just opening doors, etc.  

Describe an amazing first date. 

I always give the date in The Karate Kid the title of "the best date ever". If you don't remember it, or haven't seen it (gasp), go watch that scene. I don't want to give too much away, but......a miniature golf course is involved.

Tell me about your worst date ever.  

This girl kept basically talking about how great she was, and namedropping the whole time. She didn't seem the least bit interested in getting to know me, but was only interested in talking about how cool she was.  

You barely know me. Why are you willing to answer these intimate questions?

I am an open book, I have never had a problem answering personal questions. Also, you're really easy to talk to, so, that helped.  

Aw, thanks! If there is one piece of advice that you could give all women about dating, what would it be?   

Try not to pour everything out right away, what you're looking for, what your likes and dislikes are. Try to let everything flow naturally. I have met way too many girls recently who try to force things, and speed things up. It is definitely a turn-off, and also tends to raise some red flags.


John, thanks so much for your candor; I really appreciate it and so do my readers. I don't think you're as jaded about love and dating as you claim to be. On the contrary I think you're a romantic realist who is extremely honest, self-aware and still hopeful that things will work out with this girl you like. I really hope it does. Please keep us posted!


Also, for the record the Karate Kid is one of my all time favorite movies and John inspired me to watch it on Netflix for the four millionth time. It's a cruel, cruel summer....

Oh, 1984 you were so innocent and so was I.



What did you learn from John? Do you have any follow up questions for him? Share your thoughts in the comments!