Dating and Confidence: A Man’s Perspective

I am far from being a woman’s ideal of tall, dark, and handsome. I am 5’9″. I am Irish and Italian, resulting in a Casper the Friendly Ghost appearance. I am average-looking at best. I side more on fluff rather than buff. As smart as I like to believe I am, I question what part of me is smarter- my head or my ass? My sense of humor pushes the limits, which some find offensive. I possess a history of emotional instability stemming from bouts of anxiety and depression.

With the bad, there has to be some good, right? What I lack in those areas I make up for in charisma and personality. I always try to be kindhearted. I am outgoing and can turn into the life of the party. I work in a profession that you innately must have an internal desire to help others. I am independent and fiscally responsible. I have no kids and have never been married, so I carry no serious baggage.

Although I am not a total train wreck to date, my self-esteem leans on the lower side with dating. Even now, in my late twenties, I regress when trying to ask a girl out. I feel the pimples erupting on my cheeks, my glasses sliding my nose, and my voice cracking with anxiety. The more attracted to a women I am, the harder it is to muster up the courage.

Just last night I was at my buddy’s engagement party. I went there simply with the intention to help out and to have fun. I helped my friend set up the food and drinks. I moved around a few tables. I put up some decorations. So far, no big deal. As the party started, I went around introducing myself to couple’s friends and family members. I only knew a handful of people there and thought it might be a good idea to get to know them since I was the best man.

After about an hour, everyone finally got settled in. Contagious laughter and merriment heard throughout the backyard. It was a splendid occasion. I walked around and mingled some more like the extrovert I am. I am not going to lie. There were a good amount of attractive people at this party – both male and female. When one of the guys I was talking to pointed this out, I slightly cowered. The realization threw me off and back into my awkward teenage phase. Thankfully, I stuffed the discomfort after a few moments and fell back into party mode.

As the party winded down later in the evening, a group of us stayed behind. We slowly cleaned up and gathered at a table. At this point, the ice was broken among us. As the outgoing son of a bitch I am, I was in my element. I fed off the group’s energy. I assumed that everyone at the table was coupled up with someone else, leaving me as the seventh wheel and one woman I wanted nothing to do with romantically.

Then, the one guy next to me got up saying that he was headed out for the night. I waited for the young lady next to me to stand up as well. She sat there engaged in the conversation. Again, I waited. It dawned on me. She did not come with him. Of course, she could still have been taken, but I was already wrong once. Hopefully, I was wrong again.

I kept the table conversation going. I was on my “A” game, telling jokes with quick wit and good timing. One guy kept repeating how his cheeks hurt. Next to me still sat this super cute Latin woman. Along with everyone else, she shared in on the laughter. I was optimistic now yet approach the situation with caution.

A phone call interrupted her good time. She stood up and took the call while our conversation continued. When she came back, I took it as an opportunity for small talk. I “casually” asked her who that was and if everything was okay. She said it was just her ride coming to get her. I offered to take her home. She thanked me and said that I should have offered sooner. “There will always be next time.”

A little taken aback, I did not know how to take her last comment. Did she want there to be a next time? Was she just joking around? Did she just mean the next time we all got together or at the wedding? She also drank a considerable amount of alcohol that night, so I tried blowing it off.

Then, periodically, she leaned over to tell me a tidbit about her life. She went as far to tell me about her three-year-old son and show me pictures of him. She muttered, “single mom status.” Welp, there was my answer. She was single. Even as a counselor, I honestly could not tell if she was just striking up conversation with me while the table talk went on or if she was genuinely interested.

As it got later, I recalled I had a forty-five minute ride back home. Everyone said their goodbyes and stood up. We all hugged it out and said that we would see each other at the wedding. Here was my chance. I was definitely attracted to her. I wanted to know more about her. Maybe I could get her number or Facebook or something. How do I do it without being awkward? How do I not make this weird, especially since I will be seeing her again? Dear lord, I hate rejection. Could I deal with more rejection?

I walked to my car and drove home, replaying the situation over and over again in my head. I banged my hand against my head in an “You idiot!” fashion. What could I have done differently? Did I miss an opportunity? Was I reading too much into it?


My lack of self-confidence bit me in the ass again. Just like it has so many times before. At the end of the day, the worst thing that could happen is that she says no, and we move on. That is it. Nothing more, nothing less. Yet, my brain beats itself into a bloody pulp until the opportunity passes us by.

I bring this up because it highlights a bigger pattern. Again, I was my own worst enemy. I quite literally thought myself out of doing it. Rather than take a risk, I stayed in my comfort zone. I feared making things awkward and rejection. It was only weird because I made it weird, and the worst she could say to me was that she was not interested. It would not be the first time, nor would it likely be the last.

The what-ifs took over and drug me right out of the present moment. If I let my personality take the reins, my chances would have significantly increased. I know deep down that I am a good guy. I have a lot to offer in a relationship. Plus my track record of short-term and long-term dating shows that at least some women find me attractive. The way I found out was by trying. That was the only way to find out. I had to try. Last night I did not try, but I also would not call it a failure. It was merely a lesson learned.

Ultimately, a long-term, steady relationship is the goal. It takes work to get there and effort once it is established. Let’s be real. How many of you are still with your first boyfriend or girlfriend? Most of us failed at some point. We got up, brushed ourselves off, and tried again in hopes of doing it better the next time. Even then, it was often far from perfect. It is not always meant to work out.

Next time, I will just be myself. Without letting my mind stray too far, remaining in the moment will keep me grounded and confident. Who knows? The opportunity that presents itself may be the last one I need.

-The Caring Counselor



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