Signs You’re Dating An Insecure Guy


Name: Scared
Comment: I am with this great boyfriend. He is a hardworking businessman, with a passion for fishing. We live 200 miles red flagsapart. He cares for me and spends a lot on buying me stuff.

I met him online a couple of years ago, and we got close over the months. Problem was, I was with my ex. We became good friends, chatted a lot through the phone and through the net. He hinted me that he liked me but I did not accept him at that point because I was still with my ex.

We did meet up but just as friends. Eight months after, me and my ex were having problems so we broke off. A month later, he brought his folks to meet me and things began to look serious. We took turns to visit each other. I even got to know some of his friends.

Then another month later, he invited me to a fishing trip with his friends at the end of 6 months. I agreed and he bought the plane ticket for me. However he told me that the trip lasts a week, and we are going with a whole bunch of his guy friends. I will be the only girl there. What really worries me the most is that during the trip, we won’t be able to communicate through phones so I will not be able to contact people on land.

Recently he got the hint that I am feeling nervous about the whole thing. He tries to persuade me, even by saying that he is willing to meet my family before we take off.

His intentions seem sincere but am I being paranoid? Should I follow him on this trip? Please advice, thanks.
Age: 26
City: Brooklyn
State: New York


Yeesh.  Who the hell brings their girlfriend along on a fishing trip with the boys? That alone would make me question this guy.

To me it seems that this guy has trouble meeting and keeping women. That’s probably because he’s so needy. Between buying you gifts to blowing up a boys weekend by dragging his girlfriend along, this guy sounds like he’s profoundly needy and insecure. Let’s address the red flags one by one.

He lives 200 miles away - Did all the women in his vicinity suddenly fall into a sinkhole or evaporate? He’s broadening his search that far because he has to. Women in his area likely don’t want him.

He hung around waiting for you to break up with your boyfriend – This, too, screams, “I have no options!” Only the most desperate of people would tolerate being treated as a surrogate gal pal.

He buys you things -  Again, I question any man who feels he has to buy my affections or impress me with presents of expensive things.

What really worries me the most is that during the trip, we won’t be able to communicate through phones so I will not be able to contact people on land.

Where is he taking you that you can’t use a cell phone? Who the hell goes on a fishing trip without making sure they can get a call out should something go wrong? There’s something off here. This guy lives hundreds of miles away, you’ve hung out with him a handful of times and now he wants you to go away with him for a week with his friends? What the whating what?

This guy isn’t a sociopath. He’s just clingy and desperate for a girlfriend. If that’s your bag, go for it. Just understand that this guy will eventually become suffocating.

What’s truly troubling to me is that you see absolutely nothing wrong with the behavior that this guy exhibits other than the fact that he chose a location for a vacation that doesn’t have  a cell signal. Is that really what’s troubling you? Because this sounds like a made up concern. I have to wonder if you’re real question involves the exact issues I’ve raised in this post. Are you uncomfortable with how available he has made himself? Are you maybe picking up on how cloying he is?

If so, that would make more sense.


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4 Responses to “Signs You’re Dating An Insecure Guy”

  1. EANx Says:

    From the other perspective…

    Yes, 200 mi apart in a relatively population-dense area is a little suspicious.

    He buys a plane ticket: so what?

    No cell service? Pretty common to have no cell service several miles fishing off-shore.

    The key is how comfortable you feel. If your gut says “no” , then don’t. Don’t force yourself into anything your gut says to avoid.

    • Eliza Says:

      He’s 6’4, and insecure…all 6’4 of him! How is that relevant to the question at hand? You can be tall, and decent looking–but still be off-putting with such behavior.

      Believe it or not, some women like this type of insecurity in a man…they misinterpret all the over-bearing coddling as “interest”, when in fact this type of man can become controlling down the road. And I would feel like a major third wheel and out of place in a “all guy fishing trip”. But I guess who with your instinct.

  2. Bree Says:

    If you’re having uneasy feelings about this trip then DO NOT go. You’re not being paranoid. Your gut is trying to tell you something so listen. The guy picked a really strange way to spend time with you: an outdoor trip with a bunch of other dudes with no access to your phone??? Of course he bought your plane ticket. Thinks schmoozing your parents will placate you, PSSHHH! That’s a bad sign right there. So many red flags here. So many.

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