Ask A Guy: Is This Guy A Gentleman Or A Desparate Loser? post image

Ask A Guy: Is This Guy A Gentleman Or A Desparate Loser?

My roommate met this guy at a bar a week ago. the first date, he took her to Gramercy Tavern (one of the nicest restaurants in New York City). Last night was their second date and he took her to another equally nice restaurant. Before their second date, he had some of his friends meet her and he tells her how much he likes her every other sentence.. When she got home, she was getting concerned that this guy was a desperate loser because he was exposing all way too soon. Tonight, he came over and when I came out of my room I saw a HUGE vase of a dozen roses that he brought her. Now my roommate is convinced that he can’t get a date and probably wants to marry her next. He’s also in his 30s, a lawyer, and looking to buy a place or probably settle down. She likes him but she thinks he has no game and too much strong feelings too soon is creeping her out. What do you think? Are we just cynical and can’t appreciate a gentleman taking us out or does this guy really have signs of desperate loser?

See our guy’s response after the jump!

No, I don’t think you’re cynical for thinking those things. My quick answer is that it sounds like the guy is making up for lost time. Too much studying and never spent time being with women.

There is such thing as a gentleman, but expressing strong feelings really early on and lavishing a woman with gifts for seemingly no reason… Well… you wouldn’t see James Bond doing that :)

My guess is that she feels creeped out, he doesn’t have the experience necessary to be with her, but she feels bad rejecting a “nice guy.” It’s understandable and I feel bad for him, but it sounds like a bad match and she doesn’t want to hurt his feelings. I’m sure she’s already made up her mind to eject, she is probably just thinking of a way to dump.

In general, you might ask why a guy would come on too strong in the beginning. As with pretty much any awkward, destructive behavior in a relationship, the root of it is fear. In the case of being way too affectionate early on, it’s a case of him thinking that you wouldn’t like him if he were just “himself”. That is to say, he feels that if he weren’t trying to impress you, you would be thoroughly unimpressed with him. So, like a nervous straight-A student studying for a big exam, he overcompensates and tries to do everything “right” and “perfect.” But the reality of it is that he comes across as desperate and like he’s trying too hard.

Actually, when you go out with a guy and he acts really obnoxious, the root is still the same – it’s a matter of insecurity that drives him to act that way. Only in this scenario, he wants to prove that he’s not “that nice, pushover guy”, so he does everything on the total opposite end of the spectrum: he acts like a jerk. Acting like a jerk actually packs an additional protection since he can say that it wasn’t him that was rejected, it was the approach. Either way, he is doing his best to hide who he is since he doesn’t believe he has what it takes to stand on his own.

It’s a self-esteem issue. And it’s not your problem.

As a consolation prize, at least you know he likes you. :)

eric charles

Written by Eric Charles

I'm Eric Charles, the co-founder and co-editor of A New Mode. I love writing articles to help people free themselves from suffering and have clarity in their love life. I have a degree in Psychology and I've dedicated the last 20 years of my life to learning everything I can about human psychology and sharing what gets people out of struggling with life and into having the life they really want. If you want to contact me, feel free to reach out on Facebook or Twitter.

4 comments… add one

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j.r. clark

I move fast in relationships, and if the woman can’t keep up the pace, I lose interest FAST. If I hear the phrases, “take it slow”, or “get to know each other first”, that’s a major red flag for me.

The best relationship I was in lasted 10 years. We slept together on date 2 and began living together after date 3.

Reply October 29, 2015, 2:16 am

Eric Charles

My opinion is that it’s both. It’s true that I’ve had relationships where I was “smitten” right from the start and I was affectionate early on. Sometimes it was appropriate and the feeling was mutual. Other times I was grasping at straws – I was attracted to her and my “wanting her to like me” had me acting in a way that repelled her.

What I came to realize over time was that dating, especially in the beginning, is not just about putting stuff out there. It’s about creating and giving space for the other person to come to you and form their own opinion without you trying to force it.

When responding to this scenario, I’m picturing a guy and a girl together, there’s an awkward silence or a pause or a moment where he doubts that she likes him, and then he just starts gushing compliments and admiration to try and win her over.

This is my opinion, but from the way I read the question, it didn’t sound like the guy was even in-tune to where she was at – he was just saying stuff hoping something would stick.

Now, to your point TorontoLouise, yes it depends on context: If she likes him, she’ll like his affection. But… what lead up to her liking him. I have to imagine that the man himself, his delivery, his presence, how he held himself and how he thinks of himself plays a role in whether or not she likes him… that’s what I was speaking to. Otherwise, it’s a circle logic: it’s because of context that girl likes him > girl likes him because he has himself in order > guy acts in a way that is attractive > guy creates the context.

From that point of view, the guy and how he thinks of himself still plays a role in this. At the same time, of course, different strokes for different folks. Some girls might find one guy charming and endearing while other would find him boring and dull and others would find him obnoxious and dumb.

Reply August 11, 2009, 8:56 pm


Exactly what I was going to say, TorontoLouise.

Reply August 11, 2009, 11:43 am


Feedback from a girl.
Back when I was actively dating my experience was as follows: if I really like a guy, I found this kind of behaviour romantic and gentleman-like. If I didn’t like him or wasn’t attracted to him, it suddenly became pathetic and creepy. It’s not the behaviour, it’s the context.

Reply August 11, 2009, 11:17 am

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