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Haleth's avatar

Dating question, how do I get my head on straight?

Asked by Haleth (18947points) October 2nd, 2013

Sorry for the vague question title.

For most of the last ten years, I’ve been in relationships with one silly guy or another. I don’t really try or seek them out. Life just sends someone along, and they’re cute/amiable/interesting so we strike up a friendship, and before I know it we’ve been dating for a few months or a few years. I go into most of them feeling like, “hey, this person is all right! I’d be happy to hang out with them some more.”

Then eventually, cute, friendly, and interesting isn’t enough. All of these relationships have ended with me feeling disappointed in the guy- and in hindsight, I’ll see the the seeds of that disappointment from the first time I met him. They’ve all been fun and positive experiences during, but once they’re over it’s the same sort of feeling as when you read a trashy beach novel. Like, “what have I learned from this?” or “that’s it?”

Am I a pretentious jerk, or have I been dating shallow people, or what? This question comes from a very recent breakup, and it’s the first time I’ve finally started to notice this pattern. The best thing I could do right now is spend a good chunk of time being single and sorting things out. ...but.

I’m interested in someone, and I think it’s the real deal this time. He’s the dorkiest, most hapless guy ever, but his character, it’s so great. He’s intellectually curious, introspective, kind, and sincere; he’s always challenging himself, and always learning something new, and we share the same values. I just admire the shit out of this dude because he’s such a great person. I’ve known him for about two years.

He’s also fifteen years older, and he’s someone I know professionally. Obviously we’re in for a lot of road bumps if I pursue him. He’s gone on some unsuccessful online dates, but as far as I know, he’s never dated… anyone, really. (He’s introverted and socially awkward and has a lot of uncool, indoorsy interests, but… I have all of those things, too! It’s common ground, and I actually think his awkwardness is cute and endearing.)

For the first time, my gut instinct says this could be the guy. My brain thinks so, too. I’m inclined to spend a few months being single, sorting out my feelings, etc, before I decide whether to make a move. Beyond that, any advice?

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9 Answers

Judi's avatar

Both of my daughters went through a time like this.
They both decided to basically go on a relationship diet for six months. They made a commitment not to date anyone for six months.
My second daughter actually met her husband while she was on her six month hiatus. She told him what she was doing and told him that she couldn’t date him until her six months were up. I think she was one or two months in to it.
He actually told her that she was the most amazing woman he had ever met and that she was worth waiting for. On the day that her six months was up he had flowers and took her on their first date. They’ve been madly in love ever since. (I think they just had their 10 year anniversary but I’m not sure. )

funkdaddy's avatar

you seem to be up for introspection, so I’ll venture into the “possibly rude” territory of pointing out something you probably noticed the facts of, but may have not put together

So, a gentleman you’ve known for two years, who doesn’t seem that interested in dating, or perhaps that sought after, just became very attractive to you since your recent breakup.

No one else can pick your partners, and no one else can tell you what will work for you, but if you were my friend I would probably point out that (at least on the surface) that sounds like a rebound. We generally have “types” we date for a reason. Just because it hasn’t worked out, doesn’t mean everything you usually look for is wrong.

Maybe add driven to your usual list of adjectives and see where that leads you.

livelaughlove21's avatar

What’s actually been the breaking point with all of these guys? Them disappointing you is a bit vague.

I think taking time alone is a great idea. You quite obviously have no clue what you want. I doubt there was something seriously wrong with all of the prior men (I get the impression there have been quite a few). It’s time to look in the mirror and really figure out what went wrong.

gorillapaws's avatar

All I can say is that guys who are “cute/amiable/interesting” usually have lots of women competing for them and this tends to have a negative effect on how they value women (they’re easy to come by after all) and this tends to corrupt their nature. Some of the geekier guys can turn out to make good long-term partners. They will respect and value you. Some may take this overboard and you should put a stop to that very quickly.

Whether this particular guy is good for you, I really can’t say. It does smell like a rebound, and the fact that you work together is a major red flag.

marinelife's avatar

What can time hurt? He is not likely to get caught up in another relationship in the meantime.

dabbler's avatar

I’ll suggest you review your expectations about a relationship. It doesn’t sound like any of the past relationships really had a problem, just that they were no longer thrilling.
News Flash: just about zero relationships will continue to be thrilling for years, on and on. You will get used to each other and what you build together during the charming initial period will be what you have to share when the infatuation wears off.

Haleth's avatar

Thanks for the answers. An outside perspective is always helpful.

I’m at the beginning of a great career. So far, the work is engaging and interesting, and it’s a huge pool of knowledge- there’s always more to learn.

I’ve been interested in this guy (let’s call him Andy) ever since we met. We work closely together, but for different companies.

In hindsight, most of the guys I’ve dated were complacent. It’s like they went to college and found a job, and that was enough learning for them.

The most recent one was outwardly very successful, but he’d talk about how he didn’t believe in his company, how it was just mindless paper pushing. He wasn’t interested in changing careers, but he had no major passions outside of work (I’m not talking about hobbies here). He spent a lot of time and money on distractions, like fancy restaurants, drinking, and vacations. Those are nice things, and he was a good guy, but it seemed like he was bored with his own life. At the end, the relationship felt stagnant.

That’s what I meant by feeling disappointed in past partners, but I didn’t want to make a long question even longer. I want to be with someone who is as wrapped up in their passions and goals as I am, someone who is always learning and growing. In the dating scene in college and your 20s, someone like that is a rare find. I haven’t been dating people who share my values.

A while after my breakup, a possible new job came up. Getting a job like this has been my goal ever since I started in this field. It would also mean that I could pursue Andy. We might raise a few eyebrows, but nobody would get fired.

So I’ve decided to take this next step in my career, settle into it for a while, and then see how I feel months down the road. If Andy is the kindred spirit I think he is, waiting won’t hurt anything.

creative1's avatar

I have recently started seeing a therapist to gain insight on why I choose the men I choose to date and why I feel like I do about relationships and believe me its been through talking and better understanding as to why I am doing the things I am doing and boy has it lead me to some interesting answers. I think I still have a bit to work on but I think it will help me to find and accept the relationship that I think I will be happy with. My advice and find a good therapist you can talk to and open up to about everything and work through the issues. You will be enlightened if you do.

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