I’m Confident when it comes to dating…Confident I need more Confidence.

It’s no secret that most girls say confidence is one of the most attractive qualities in a guy. I mean, I can’t blame them – a guy who is proud of who he is, regardless of what other people think, says a lot.


I wish I was the guy who would walk in to a room without being self-conscious or always thinking “how is he/she viewing me.” I’m not this guy…unfortunately, it’s the opposite. I’ve always been self-conscious and worried about how people view me – especially when it comes to the whole dating game. My confidence has definitely taken a hit with each girl that ghosts me, date that doesn’t pan out, dating app message that goes unanswered, and of course, every relationship that doesn’t work out really is a blow to my confidence.

So today I was listening to a dating podcast that addressed confidence. They spoke of how a guy shouldn’t worry if a girl is going to reject him – if she does, her loss. He shouldn’t change what he does to come across as “the nice guy” or go out of his way to impress a girl. Around this point, I paused the podcast and realized they guy they are talking about not becoming, is basically describing me. I won’t lie, when I’m dating a girl, I overthinking E-V-E-R-Y-T-H-I-N-G. My racing mind sounds like the following:

“why hasn’t she responded, its been 9 minutes? Did I say something wrong? Should I have kissed her? She said she had fun but what’s she really think? When do I contact her again? Should I play hard to get? + about 100,000 other questions” 


The million dollar question right here. If I knew the answer, boy would that change things. I don’t think there is one reason, I think it’s a combination of many factors

  1. My dating/relationship past
    As noted above, my confidence takes a hit every time there is a girl I’m interested in who isn’t feeling the same way. If she’s honest with me about it, it’s still painful; however, it’s a lot easier pill to swallow that the girls who fall off the face of the earth after telling me they’re interested. I try to tell myself that there are other fish in the sea but I’ll be honest, sometimes it feels like the pond is going dry.
  2. My looks?
    I’m not 6’5 with huge biceps and a 6-pack. But, I’m not on the other end of the spectrum either. All 3 of the websites I checked for what weight I should be for my height say that I’m in the average weight range. I definitely have an extra few pounds of fat that I would love to turn to muscle but I think everyone does, for the most part. However, growing up, I was the chubby kid and I think I still see myself in this light, which absolutely hurts my confidence…big time.
  3. Education/Career?
    I’m honestly not sure how this one effects my confidence. I graduated college and started in the working world right after. I’ve been very successful in developing a career, make good money, and honestly love what I do. I wake up everyday happy to work and I am confident in the work I do – I know I am good at my job. However, I’m not a lawyer, a doctor, or an MBA. Many times I wonder if this effects how women see me. I don’t think it does; however, I do think at times I am self conscious about not having a graduate degree.
  4. Psych myself out
    I often wonder if that fact I know that confidence is not my strong suit hurts me. Do I psych myself out? I know that I do. I get anxious and overcome with fear, which in turn, effects how I interact with women. People have told me before, “don’t worry about what they say, just be you.”……Buddy, where is the worry switch that I can turn off? Once you tell me that, I’ll give this a try!

To say I’m jealous of those guys who know they look great, have killer charm, and are confident in every move they make is likely the world’s biggest understatement. I don’t need to be this guy; however, I would really like move closer to this magical person and away from someone who is always worried about being judged and takes things too personal. Any great suggestions out there? Even a decent one would be most appreciated!



Pet Peeves of Dating

Who doesn’t have a pet peeve or two? Or for some people, it’s more like 15. You know who you are….I’m proud to say that I’m one of them….just on the topic of dating! Yikes, now that I am putting that in writing, I’m starting to wonder if maybe why this is why I am single!

Well, here goes my list of dating Pet Peeves. If you have any that I missed or there are any below you can add to, please comment back – would love to hear your thoughts.

1. Not offering to pay

So, this one is about effort and expectations more than anything. Especially on a first date, I insist on the partaking in the archaic tradition of the guy treating the girl. I think it’s outdated and ridiculous; however, society has done a great job at making me feel like I need to follow this cultural norm and I am knowingly enabling it by partaking. However, it really rubs me the wrong way when a girl won’t even offer to pay. When that happens, I honestly feel like a meal ticket more than anything.

So, I’ve been asked before, “What do you want the girl to do/say when the bill comes.” I think she should offer to pay and after I decline to take her up on that, she thanks me (more on this below). If she’s feeling me and wants to get together again, I love it when a girl then replies that she will let me pay this time, but next time it’s on her. When this is on the table, I do take her up on the offer. However, the reason I love this has nothing to do with money – it’s 100% because it shows me she is not only interested in me but already thinking about the next date.

2. Not saying “thank you”

Believe it or not, I would say at least 50% of the dates I’ve gone on where I pay the bill, I don’t even get a Thank You.

                            DID YOU GO TO KINDERGARTEN?? C’mon, this is basic manners.

Here again, I’m left feeling like a meal ticket. Regardless of whether you like me, love me, or hate me, if I treat you to dinner, I feel that the two words “thank you” should be uttered at least once.

3. Not responding to texts/calls for hours

I’ll preface this by saying that I grew up on the east coast of the US and have lived most of my life near some of the busiest cities in the country. We all know that there is some truth to the stereotype of people from the east coast being impatient – I know that I am in many respects.

Ladies, I’m about to let you in on a secret of what goes on in the head of this guy….when there is a girl I really like and we are texting back and forth, after I hit send, I’m very anxiously waiting for your reply. It’s in the forefront of my mind. I don’t expect a response in 2 minutes; however, outside of work hours, after about 15 minutes I may start to get a bit anxious. After 30 minutes, the anxiety picks up. Once we reach the hour mark, I start to have the following go through my head…

“She’s probably on a date with another guy”

“What did you say in your last message that could have been taken the wrong way?”

“She doesn’t like you anymore”

This is unhealthy paranoia – I know that. However, many times, how quick you hear back from someone is telling. Many times it’s not – the reason it took 4 hours to reply is many times unrelated to me. This is a Pet Peeve that is more of something I need to work on about myself; however, all the ladies out there should know that those anxieties you feel when we don’t response, are felt by guys too.

4) Significantly Altered Dating Profile Pics 

Have you ever gone to meet someone from Tinder, Bumble, etc. and get to the bar, look around and don’t see them. Then, you hear your name and upon locating the person calling you, have no clue who that person is? Well, I’ve had that happen, multiple times.

We all have pictures that show us 20 lbs lighter or ones that are touched up using one of the many iphone apps at our fingertips. It’s awfully tempting to put up an altered photo or one from 2011 that seems more attractive; however, is it fair? I don’t feel it is. I’ll be honest, I’ve touched up a phone or two before but never to the point of looking different than the guy a girl is about to meet. I don’t hold it against the person if they are overweight or something like that; however, I do hold the dishonest peace against her. This is the worst way for things to start when dating someone. Be honest and be you. Otherwise, I can’t see how things will ever work out.

5) Ghosting

I could rant about this one for a day. This is the biggest pet peeve of dating for me. Of course, there are scenarios that are exceptions (ie – someone has abusive tendencies). However, should there not be an exception that warrants ghosting, it’s downright cruel.

We all understand that when dating someone, it’s likely one of us is going to end things, at one point or another. So, there is a risk of getting hurt that both parties take when dating; however, I feel that we owe it to each other to mitigate this pain as much as possible, should that arise. Falling off the face of the earth and ghosting someone is not fair and just prolongs the pain of things not working out. Confronting the other party and making it clear this isn’t going to work will be difficult and could hurt them. However, it’s a pain that provides a form of closure and allows them to move on without you.

Relationship Relapse?

Last week I had my own version of a release. A dating relapse, that is.

Last week was Thanksgiving and my family likes to make it extra exhausting and do lunch at my dads side and dinner at my mothers. This means I get the “pleasure” of sitting through people talking about how thankful they are for their significant others twice. Don’t get me wrong, I have so much to be thankful for – my health, family, friends, job, etc. However, the significant other piece is still an “open wound” after my break up so I was extra cognizant of it.

So, at the end of the night I did something I’ve never done before….I texted my ex. I just wished her a happy thanksgiving and said that I was thankful for the time we were together. Despite there being minimal substance to the text, as soon as I hit send I was overcome with a feeling of sadness and regret. I felt like I had just sent her a message begging her to come back to me and the feelings of missing her came right back. She never responded to me, but I’m not surprised. In a weird way, it’s probably a good thing.

I’ve had break ups before and unless we ended things with the understanding we would try to continue a friendship (which never works), I always have moved on and not tried to reopen the lines of communication. That has to be why this feels like a relapse to me. But is it really? I don’t think so, but would love to hear your thoughts.


Back in the Dating Saddle

In a past post, I shared the details of how my last relationship ended about a month ago…days before my 30th birthday. In the last month, I’ve had a whirlwind of emotions go through me – for the first couple weeks, it was mainly sadness, confusion, and grief. While we were only together for a few months, she had become a big part of my life and I saw that only growing. I had been invited to her family’s events a week before I had “the bomb” dropped on me so she wasn’t exactly cutting me out of her life slowly.

This grief and sadness then turned to anger. How could someone who supposedly cared about me do this? I completely understand that you need to be true to your feelings and don’t fault her for that. However, what I do have a problem with is how I was treated in the aftermath, but that’s a whole other story in itself.

Now, I’ve moved on and am back in the saddle and ready to move on. I have 2 dates on the agenda for this week. So, with that being the case, the whole first date etiquette is on my mind so I wanted to take a look at it:

Where to Meet Up? Such a simple thing, yet so important. Where are we going to meet? My go-to is a restaurant with a bar…let’s be honest, nothing to kill the first date jitters like a little booze!

Who Pays? This is not even a question in my eyes…the guy does. Why? Because that is the rule. I honestly think it’s stupid and archaic, but because society says that “gentleman” will pay on the first date, I don’t dare touch this social norm.

Goodnight Kiss? This is such a polarizing topic – it makes the topics of universal healthcare, immigration, and marijuana legalization seem innocuous. I’ve had many debates with friends about what to do at the end of a date – kiss or not? Some of my friends are adamant that you got to kiss the girl, otherwise you are entering the “friend zone.”

However, I don’t subscribe to this school of thought. It seems a bit weird to me kissing someone that you met a few hours ago. I tend to go in for the kiss on the 2nd date – I mean, those extra 2 hours really make a difference right? But in all seriousness, this gives us both time to digest everything and inevitably find out whether there is interest or not on the other end.

When to Contact Next (and who should) if you want to go out again? We’ve all heard of the 3 day rule. “You have to wait 3 days or she will feel you’re too eager – you got to play hard to get.” This is another one that I personally don’t subscribe to. Maybe it’s because I’m impatient, but I’m usually texting the girl that same night saying I had a great time. I won’t life, a girl gets major brownie points when I pull my phone out to send this, and she has beat me to the punch. In those cases, I know that she is considerate, appreciative, and of the most importance, interested. I feel that you have to go with your feelings on this one– some people will wait, some people, like me, want to reach out right away.

What to do if you don’t want to see the other person again? Inevitably, most dates will end with at least one person not feeling it – it’s the nature of the beast. However, I still ask myself every time I’m the one who is not feeling it,“what should I do?” And, every time I do the same thing, fall off the face of the earth and not contact her. I’m not proud of this but what is the better alternative? Sending a text message that says “Great meeting up with you but I’m not feeling it” would be just weird. Of course, if the girl ever contacts me and gives the impression she wants to go out again, I’ll say “thanks but no thanks”….in a much nicer fashion.

So, give me your thoughts on these items – what am I doing right? What should I change up?