Demystifying Dating: Answers to Your Dating Questions From 5 Real Dudes

A few weeks ago, I published a blog post all about dating and relationships- Do You Follow “The Rules”? Getting Real About Dating. After hitting publish, I was flooded with comments, emails and tweets. It appears that everyone has an opinion or story when it comes to this hot topic. (I know I certainly do).

After the post went live, I started thinking about how while dating isn’t easy for the ladies, I’m sure it’s equally frustrating for men in different ways. I started wondering what guys are thinking in certain situations. I wondered if they confer with their friends on texting. I wondered about what types of insecurities they faced on first dates. I wondered if they thought online dating was as frustrating as I think it is. I was curious about what annoys them most about dating.

So…I decided to ask them. I pulled together a panel of five real dudes (all of whom I know in real life, so I can personally vouch that they are all good guys).

In today’s post, you’ll meet them. They are answering YOUR most pressing questions about first dates, online dating, text messages, making plans, becoming exclusive, who pays on dates, who should make the first move and so much more.

These questions were compiled by a panel of about seven women, some single and some in relationships.

Here’s what guys are really thinking when it comes to dating and relationships…read on.

OH, and stay tuned! This series will be fair and balanced- next week, we’ll hear from a panel of ladies answering questions about dating and relationships from men. Guys, have a question you’d like to submit? Leave them in the comments below!

Meet The Dudes

demystifying dating- Jessica Lawlor

Say hello to…Jason, age 39 from Hatboro, PA
Relationship Status: Married

Say hello to…Steve, age 34 from Horsham, PA
Relationship Status: In a monogamous relationship

Say hello to…Phil, age 25 from Manayunk, PA
Relationship Status: Single

Say hello to…Paul, age 36 from Philadelphia, PA
Relationship Status: It’s complicated

Say hello to…Mike, age 30 from Delaware
Relationship Status: In a long-term relationship

Let’s get to the questions! Here we go.

1. How do you typically meet girls? (Apps like Tinder or Hinge, online dating site like OKCupid or eHarmony, through friends, at a bar, etc.)

Phil: I have had the most success meeting girls either through friends or online, specifically OKCupid.

Jason: Mainly through friends or coworkers. Happy hours and parties, etc.

Mike: My last three relationships have been (in order) at a bar, OKCupid and then a friend of a friend.  OKCupid was by far the worst experience as it is hard to gauge a person when they have an unlimited amount of time to edit their messages. Even when I met a girl at a bar it wasn’t a cold pickup, she had known a good friend of mine and we just happened to start talking (not quite friend of a friend, just happened to be in the same area and knew the same person).

Steve: I smile and say hi.

Paul: It’s usually been through just day-to-day life, either at a job, through friends, yoga, etc.  I did try Tinder for a very brief time, but it was definitely not for me.

2. Do guys confer with their friends on how to reply to texts from women? (Be honest!)

Phil: Yes. While I may be breaking some sort of unwritten guy code by saying so, generally I will at least run something by a friend when I’m texting something to a girl, especially if I don’t know her very well or met her online.

Jason: No. Even if guys aren’t sure what to do, I think in general it’s awkward to talk about it with friends.

Mike: YES. It is a lot easier to reply to a text when it has zero impact on you. I’ll tend to overthink a reply but a friend will just come up with something simple.

Steve: Depends on the text, but yes, I have…I cannot speak for all guys though.

Paul: Some do, some don’t. I do for sure. Just last week actually, a friend of mine was asking me what he should say via text. As a guy, I don’t think we always feel comfortable asking each other questions about how a date went or what to say to a girl you like.  We make it a joke to ease into the transition of actually having a substantial conversation about feelings. What I’m trying to articulate is that men aren’t as comfortable being vulnerable and letting their guard down to ask advice, so by joking about it, it eases the transition into a “real” conversation.

3. What are you most nervous about when you go on a first date?

Phil: Obviously, you want it to go well, so that’s the main reason. But, more specifically, I worry about running out of things to talk about and getting stuck in a date where there are lots of long, awkward pauses.

Jason: What to do if the date bombs. How to get out without wasting everyone’s time and without seeming like a jerk.

Mike: Having something to talk about. I hate small talk and I am not at all good at it, so if a good conversation doesn’t hit, I know that I’m in for a long night.

Steve: You shouldn’t be dating if you get nervous on a first date. I rarely get nervous…ever.

Paul: My appearance for sure. I feel like I’m a nice person and that I can get along with almost anyone so the conversation part is fun and easy, but I never feel like I’m good enough appearance-wise.

4. What annoys or confuses you most about women when it comes to dating?

Phil: I don’t like to generalize because there is no way every single girl does this; however, I’ve run into the following scenario a few times. I’ve gone out with a girl, sometimes more than once, and things have gone well, at least from my end. Everything the girl is saying indicates she’s interested but at some point, I’ll text her and get no response. I don’t expect a response right away or even that day, especially if it’s a girl I’ve only gone out with once or twice, but we live in a world where everyone is glued to their phone, so it just seems insulting to go radio silent entirely.

Female friends of mine have said that the person is probably trying to avoid hurting my feelings because they are not actually interested, which is fine, but it hurts more to just be frozen out because there is still that lingering doubt. I’d rather just be told up front and not be given the run around. There’s no harm in not being interested.

Jason: The facade. That dating phase where people act like their ideal version of themselves and only slowly reveal their quirks. It’s better to be yourself from the start.

Mike: Girls will seem like they are not interested and then get angry with me when I stop contacting them. I was once dating a girl and asked her to come over and she made up some lame excuse so I just stopped talking to her, come to find out later that she wanted me to beg and plead to see her.

Steve: Women are rarely honest. They would rather lie to spare a stranger’s feelings instead of being honest.

Paul: I think woman are very fickle, but there is nothing wrong with that. It’s just frustrating because I never really know what they want.

5. Do you find that you count certain girls out immediately because they aren’t “your type” or fit a specific physical mold?

Phil: I don’t only go for a specific type, as in I will only date girls that are a certain height or a certain hair color, but physical attraction is important, so if I am not attracted to a girl, I won’t pursue her. With that said, I don’t expect every girl to be attracted to me either.

Jason: Absolutely. Gut instinct on physical attraction is important.

Mike: It is hard not to. Anyone who says that they don’t consider looks are a liar. If you walk into a room with 50 girls and you don’t know them then the only thing they you can judge them on is looks. So I guess it is better to say that I don’t rule them out, but you prioritize who you will go after.

Steve: Absolutely. You need to be physically attracted to someone…otherwise you are just friends if at all.

Paul: I’m sure I have, it’s a shame because everyone has something to offer and I’m sure I have missed out on some amazing woman due to being shallow.  

6. How do you feel about women who are aggressive when it comes to dating? Do you like it or do you prefer to do the chasing?

Jason: It’s great. Again, people need to be themselves. And if a woman is naturally aggressive, she should just be that.

Mike: I’m fine with the aggression. Going back to a previous answer, it lets me know where I stand. It also makes it easier to see through games and see if you really make a connection with a girl.

Steve: Love it. Chasing is fun, but it gets old. You never need to chase the ones that deserve to eventually meet Mom.

Paul: Since I’m so shy, this is usually the only way I do get dates. I need to know almost 100% that the woman is interested before I put myself out there.  The women who are confident enough to ask you out are, in my experience, also very independent, which is great, but I like to take care of people and there have been clashes in my relationships.

7. You have what appears to be a great first date and you really seem to hit it off. Many women have said after this happens, a guy will continue to text them, but not necessarily ask for another date. Why do you think this happens?

Phil: I think it depends on the time frame. If he hasn’t asked for another date after a week or so, then he is either a moron or not really interested. If it’s just the next day or two, he’s probably just making conversation because he wants to talk to the girl.

Jason: Fear of rejection.

Mike: Two reasons. One is that a guy could be playing the field and keeping a girl on the back burner. If you have a good time with a girl but you have to remember that a guy might be talking with a few others.  Second is that maybe the guy didn’t have that good of a time and wants to just be polite.

Steve: This guy is immature and just keeping you on the back burner. #hesjustnotthatintoyou

Paul: I’m not really sure. It could be that he’s not sure if you thought the date went well and he doesn’t want to be rejected, maybe he was looking for something casual and he realized the woman was looking for a relationship and he didn’t want to be an asshole and lead her on.

8. Who should make the first move? Does it matter?

Phil: It doesn’t matter at all. I think adding pressure to either person just makes it less natural.

Jason: Ugh. This is tough. It totally shouldn’t matter, but there’s a certain masculinity to making the first move. I think a lot of guys want to be confident and powerful in a relationship.

Mike: It doesn’t matter, there is so much you can read online about non verbal signals to where it can be done by either side. You don’t want to make a move without one as it could be seen a creepy or misleading depending on which party does or does not want the “move.”

Steve: The more aggressive person. It really doesn’t matter.

Paul: It’s always great when the woman makes the first move, but I feel like it’s more my responsibility as a man. I also don’t really think it matters, but society has sort of dictated that that is the man’s “job” for better or worse.

9. What does it mean when a guy won’t commit to plans? I’ve experienced and heard from fellow women that guys will make non-commital plans for the general future, but don’t necessarily nail down a date.

Phil: It means they aren’t that interested. It’s a shitty move on the guy’s part, but that is unfortunately the reality.

Jason: I’m sure there are guys who are just assholes who want to keep their options open. But more often, I’d guess it’s fear of rejection. Trying to set a date and having the object of your affection be wishy washy about it sucks.

Mike: Guys tend to make plans the night before with their friends, so it is hard for them to understand how much girls like to plan ahead.

Steve: He’s playing a game called letting you down easy while I keep looking for something better

10. Who pays for the first date? (And at what point do you feel it’s appropriate for the girl to either split or pick up the check?)

Phil: I always insist on paying unless the girl is uncomfortable with it. After the first date I generally continue to pay until the girl offers to split it (after a handful of dates, it’s nice if the girl offers) or until you reach a point where you’ve gotten more serious in the relationship.

Jason: Maybe this is changing, but I’ve always thought the guy should pay despite who makes more money or whatever. Every once in a while, the lady can pick up a check as a nice gesture, but splitting a bill or trying to keep it even feels petty. The guy should be willing to pay.

Mike: The guy does, it saves an argument and lets the guy show off a little bit. It might be an old fashioned type of thinking but guys want to show off that they can support a family and this is the first step in showing that (unless you want to look through his bank statement on the first date).

Steve: In my opinion, always the man! When you became exclusive in a monogamous relationship, it’s appropriate to split or have the woman pick up the check.

Paul: This one is easy for me. I will always pay for the first date, and second, and third, etc. I think it’s appropriate for the woman to pay whenever she wants, but I like taking care of people and will do my best to pay until the very end.

11. Do you have a timeline for how dates should progress? For example, at what point do you begin picking her up at her house, rather than meeting somewhere? At what point, do you just start lounging around together rather always going out on dates?

Jason: Definitely not. Hanging out at home can even be a good early-stage date if you already know the person well (like a coworker). Conversation and chilling is awesome.

Mike: No, you really can’t put a timeline on anything, it leads to stress and people getting unnecessarily upset over a relationship. Normally the first date you meet somewhere, but by the second if you don’t feel comfortable letting the other person know where you live then the relationship isn’t going to go anywhere.

Steve: I prefer to pick the lady up. It’s the traditional man in me. What’s most important is how comfortable she feels though, so it’s up to her.

Paul: I feel like this is all stuff that happens organically and is different for each relationship. It doesn’t take me long to feel comfortable with someone and I can start lounging around together almost immediately, but maybe someone who is afraid to let others in would take longer. I always feel most comfortable in a relationship, so when dating I tend to force the situations where we can just be together. I’ve always moved way too fast and have ended up in situations where I thought I wanted to be, but in retrospect was only there because I was scared to be alone.

Also, I would pick a girl up on a first date, but I understand how that can be concerning for a woman.  Something I had never really thought about before was that the dangers of dating are more or less only an issue women face. I’ve never went on a date worrying if the girl is a dangerous person and could hurt me, but that is actually a legitimate concern for woman.

12. What do you expect from a girl in the first few dates?

Phil: Putting expectations on any date is dangerous because it constricts how you view it. If you want it to go one way and it doesn’t, even if the other way it went was good, it may sour how you feel about the person. I generally just hope to have a good time and see where it goes from there.

Jason: Sense of adventure (trying new restaurants, going to see a band they don’t know, etc.), calm and casual attitude, low pressure, easy conversation.

Mike: I think it’s hard to expect anything until I know the person because people come from different backgrounds.

Steve: The real her…no games or lies! A kiss is a must in that timeline.

Paul: Nothing really, that’s not to say I don’t have tons of expectations later on in the relationship, but in the first few dates it’s so casual. I don’t even really expect responsiveness to texts or calls, but it’s always nice when there is.

13. Do you have any dealbreakers?

Phil: If you don’t like Rihanna then I don’t want to know you as a person. Seriously, having dealbreakers is a tired trope made popular in movies and TV. Obviously, if a girl is a serial killer, then she’s out, but just because she may not agree with me about something doesn’t mean its automatically over.

Jason: Bad (or lack of) sense of humor, politically conservative, unhealthy diet and fitness, uber-religious.

Mike: Girls who don’t have their life together. Back in my mid 20s if a girl said that she was just working an entry level job with zero education or ambition of moving upwards, that was a deal breaker for me.

Steve: Of course…who doesn’t?

Paul: I can’t say for sure, I try to keep an open mind, but there are certain things I can’t overlook, racism for example, which is a situation I’ve run into.

14. Do you play any “games” when it comes to dating? For example, do you think about how long you should wait to text a woman back?

Phil: I used to do that type of thing because TV and movies made it seem like that’s how you do it. Then graduated from high school and realized how stupid it is. I don’t want someone to play games with me so why should I? I generally try to be as blunt as possible. If I like a girl, I text or call her when I want to talk to her.

Jason: Never. That’s a terrible way to go through life. Gotta be yourself and let the chips fall where they may.

Mike: However long it took them to text you back. I don’t do this to try to prove anything, but I don’t want to look like I am staring at my phone waiting for the person to text. Once with a girl I decided that I wasn’t going to text her at all one night (a buddy of mine thought she was crazy) and she wound up texting me about 25 times that one night without a single reply.

Steve: No games…tell it like it is…always have and always will.

Paul: I’ve waited a while to text back, it’s always been a case where I wasn’t really interested and it was my cowardly way of subtlety hinting that I wasn’t.  In retrospect I should’ve just been honest.  If I am interested, I just go for it.  It’s what I want and I really don’t like playing games.

15. Do you believe in dating rules? (Like in my blog post and the book I read) If so, what rules?

Phil: I don’t believe in dating rules. People are not machines that all run the same and if you follow a magic set of instructions everything will work out. I just go into any dating situation and try to be who I am and no one else. If that’s enough, great, if not, then no harm done.

Jason: Not really. Unless the rule is to relax and have fun.

Mike: Not really, I just try to be as open as possible because when you have rules you limit how fast you can get to know somebody.

Steve: Nope.

Paul: I honestly don’t feel like I’ve been on enough dates that I would be able to think about rules. I’ve always looked at a date as just hanging out with another person.  I feel like I can easily make a connection with most people.  I always see the best in everyone.  That way of thinking has definitely caused me a lot of heartbreak though.  I tend to overshare and depending on the situation I think that can be a mistake.

16. How soon is too soon to “lay down the law” on what you expect from a relationship?

Jason: Never too early. I love transparency.

Mike: When you feel like it is starting to get serious, until then have fun!

Steve: The sooner the better.

Paul: I don’t really have an answer to this question because I feel like every relationship is different.  Every relationship I’ve ever been in has been serious from the beginning.  We just wanted to be together everyday for the first couple months and there wasn’t even a need to discuss expectations.  It just was.

Such juicy information, right?! Thank you SO much to my panel of dudes for taking the time to share your innermost thoughts on dating and relationships.

What do you think? Ladies- do any of these responses surprise you? Men- are these thoughts in line with your thinking? Leave your thoughts in the comments below.

Remember, next week, we’ll hear from a panel of ladies answering questions about dating and relationships from guys. Have a question you’d like to submit? Leave them in the comments below!

Want more gutsy content delivered straight to your inbox twice a month? Be sure to sign up for my FREE #GetGutsy e-newsletter filled with inspiration, ideas and action items to get out of your comfort zone. When you sign up, you’ll also be sent a FREE copy of the Get Gutsy ebook, filled with 19 inspirational stories to help you get gutsy.


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Meet Jessica

I live by the saying “Life begins at the end of your comfort zone” and help others do the same to reach their biggest, brightest goals. Read my story here.

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