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How to Overcome Insecurities When Dating as a Guy

Dating as a guy can suck, but don't fret, there may be a solution or two for you.

By Dr. Harmon LovePublished 7 years ago 8 min read

Take it from me, when dating as a guy, it can be a complete crapshoot. As somebody who has dabbled in spur of the moment conversation and the online dating scene (with varying success for both), it is easy to develop insecurities. You will rack your brain over why things don't work, what your limits should be and even when things seem to fall into place.

According to, guys face insecurities when dating for a number of reasons. Most of them seem to be surface level worries, but from personal experience, I can confirm that some of the other ones are true. What I can do is review the grandest of the insecurities that men have faced during dating and comment on how to overcome them.

Looks and What is Behind Them

The first thing on every guy's mind while dating has got to be the looks. And not exactly the looks of the other person, but predominantly themselves. Men will go all-out to look great on a date night and are probably expecting a woman to reciprocate.

Personally speaking, to overcome this insecurity, I did just one thing: be myself. And myself on a good day is wearing a not very wrinkly shirt, pants with no holes in them, I've trimmed up the beard, and put some gel in the hair. This usually happened when I knew I was going on a date. Speaking to somebody random, well, I could be sweaty as a pig in a concert venue wearing yet another band t-shirt. And it works.

But the insecurities don't stop at looks because you are worried about what your date is really like. Sure, her online profile might have said she's a Ranger fan, but in your head, you are worried that she doesn't know the team lineup by heart. Maybe you really like the way that blouse looks on her, but you're fretting over where the conversation is going to.

Just go find out. If it turns out you have nothing in common or it just isn't gelling, what's the worst that has happened? You got to know someone a little, spent an hour and change with them, and maybe dropped a few bucks on drinks. That's the beauty of being different. Even the ones you think might be on your level, there is going to be something that sets them apart from you. And that is nothing to be insecure about.

The Actual Date

The date gets planned. Often times, men will worry about where they will be taking their date. Should I take her to a ritzy joint to really impress her? What if the place I do wind up picking doesn't go over well? Important things to consider, but ones that are easy to overcome.

First off, figure out what kind of person you are dating and take it from there. If they enjoy casual fare, don't be afraid to show them a good pizza place (pizza is always a winner). If they tell you they have a favorite dive bar, you can probably get away with taking them to the town watering hole. And if you met at a location, well, problem solved, but don't suggest to come back, especially if it is a frequent stop for them.

Conversation can also be nerve wracking. Am I talking too much? Too little? Am I steering it down a bad path?

This is one of those take a breath and chill moments. You are not forging a peace treaty here, just going on a date. Toss the ball between courts equally and keep it simple but interesting. If it's something you already know, it's not a dead topic, but rather something you springboard off of.

"So, you're a Rangers fan?"

"Yeah, since I was eight."

"Have you ever been to a Stanley Cup Playoff game?"

"No, have you?"

And so on. This isn't your opportunity to hog the conversation, though, something I am guilty of when I get on a tear. Never said that just because I was offering help, doesn't mean I am not without my own insecurities I am trying to fix.

Lastly, dating as a guy often has us looking for vibes. Are you hitting it off or not with this woman? Did it go well enough that it warrants a kiss goodnight? Should you try to lean in for a kiss? I have often found myself asking these questions to myself in the heat of the moment.

Unfortunately, I don't think there is much to solve this insecurity, but you can treat it as a feeling of excitement rather than trepidation. If you are on your game, between the two of you, you can probably figure it out if you want to lean in for a smooch. From there, it is a period of growth if you continue to see each other.


Booze has always played an integral part in the world of dating, for good and bad. When is enough enough? When is too little too little? What is the right balance? Dating as a guy, we often wonder where we need to cut it off.

I think in order to overcome our insecurities, we need find the balance and judge from there. Have a few drinks together, enjoy a bottle of wine at at dinner. But never force it, because that's when problems are going to flare up. Even if you just met at the bar and had success with buying a round, don't feel like you two need to push it because you are out drinking. If you hit it off, then you can learn what it is like to share a mutual hangover after a long night out.


Ah, the eternal thought on every man's mind, right? The sad truth is that dating as a guy has put a thought into our minds that sex rests just around the corner for us. Because we looked so damn good and talked just the right amount and impressed with our restaurant of choice. We want that sex.

Well, stop. Sex is an incredibly intimate experience. And people should respect that if the opposite party is looking to feel out the dating scene. Is hookup culture a thing? Absolutely it is but that's another conversation altogether. I guarantee you, in the realm of dating (like actual, serious dating), sex happens when people feel comfortable around one another.

I would suggest putting your energies into other places if you have hit it off with somebody and put sex on the back burner from the get go. Talk about your shared interests, find a place you both enjoy and go there, see a movie. Establish that comfort before the sex. It's a matter of trust and respect and in due time, you will find both of those.

Did I Screw It Up?

This one rang true with me. This seems to be the greatest insecurity when dating as a guy. We put so much thought into a first date and even a second or third or a weekend with your potential partner in the future. With online dating, it exists for that reason. People are looking for relationships, whether to learn or to find that certain someone. And sometimes that spark flies in our head, but not the other. You could be into the person based on the first date or you might realize it on your fifth date. And then the other person says, Sorry, I'm not really feeling this.

What happened? What did I do? Was it something I said? That restaurant was a bad choice, wasn't it?

No, calm down, and take a breath. The best advice here is to take a chill pill. It is also called online dating because it promotes just that as well. Dating. Go on twenty dates if you need to. Talk to people at the bar. There is nothing with wrong with dating, unless you turn into a serial dater, then we might have a problem. Find people you are comfortable with and maybe you will come across what you are looking for. And always remember that you don't truly know somebody until you interact with them in person.

Where Do We Go From Here?

Is there more to experience from this encounter? Dating as a guy, this could be one of the easier insecurities to overcome. And I say this based on experience. Nobody is saying you have to spend the rest of your lives with somebody you met. If it doesn't go well, it doesn't go well. No harm, no foul. It is almost like building up a tolerance.

But say it does go well? Then abandon your insecurities and feel it out. Go on another date. If the signs point to yes, then see where it goes. And don't worry about the long term plans for now. Too many young people freak over long term plans and what they need to have locked down. We are young. Let's enjoy our lives while we can and see what is in store for us.

Yes, entering the world of dating as a guy can be intimidating, even terrifying, but once you overcome those insecurities, you just might be able to find what you have been looking for all along.


About the Creator

Dr. Harmon Love

Sex therapist, avid reader and movie fan. Sex is not love but there is no love without sex.

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