When Is It Wise To Shoot Out Of Your League?

Name: Alexcourntey-cox-cougar-town
Comment: I just sent a message to a woman I found through an online dating site (OKCupid). This girl, let’s call her Megan, seems fantastic– she’s a nurse (I’m a first year medical student), she enjoys a lot of the same things I do (camping, cooking, giant dogs, passionate sex haha, etc…), and not to be weird but the ‘explanations’ she wrote for all of her personality survey questions really made me laugh. The point is, she seems special, and I’d like to see where things go with her. Here’s the rub though: She’s 28 and I’m barely 23. I’ve never dated an older girl before, and to be honest it’s never been much of a concern for me. Now, though, I’m a bit worried that she, like most women I suspect, would prefer an older guy, and won’t be interested in getting to know someone 4 years younger than she is. (Not to mention, I’m still in school and will be for at least the next four years.) Maybe it’s not a good idea in the first place– I can think of about a dozen reasons why not to pursue this– but honestly, I don’t come across a lot of people I could envision having a serious relationship with. I don’t want to miss out on my chance to get to know this girl. Anyway, any advice you have on my situation would be greatly appreciated. Thanks so much!
Age: 23
City: Iowa City
State: IA

You’re right in your assumption that many women, especially when dating online, dismiss the emails from the younger guys. That’s swell that the thought of dating an older woman has never been a concern for you. But you’re not the only one involved in this scenario. She probably gets  a ton of messages from guys just like you who think she’s special.

I think her bigger concern would be that you and she are in two different places in your respective lives. You’re just starting medical school. I’m sure, as a nurse, she has an idea of what you’re about to experience. She’s familiar with the busy schedule, the unavailability, the time constraints, etc. That is a valid concern for her.

Yes, maturity levels might come into play as well. From my experience, dating someone under 35 when you’re a few years or even several years older can be trying. There’s this lack of accountability and disorganization involved that makes dating someone younger absolutely maddening. Younger men and women are still figuring it all out. There’s still a level of self-absorption that is present with many people in their twenties to early thirties. Which isn’t necessarily an insult. At that point in someone’s life they’re trying to establish themselves. It’s hard not to be wrapped up in your job or school or your social circle. We all go through that transition period where it’s all about us for the time being. That, and not the lack of common interests, is what concerns me when presented with an opportunity to go out with someone under 35.

She also might dismiss you as yet another younger guy looking to bag an “older” woman for the story. For that you can thank all your bros who don’t know how to get it right and behave properly. They don’t see women as people, they see them as objects. So, if you do want to catch this woman’s attention, talk to her like  a peer.  You’ve got medical school and training involved. Maybe use that as a spring board for conversation. Talk to her as an equal and ignore the age difference completely. There’s nothing more awkward than when someone emails you and starts off by admitting that they “know” you probably won’t respond or might dismiss them.

I’ve often said that I think we know when we’re encountering someone out of our league. I think it’s good to occasionally step out of that comfort zone, if only to make yourself more available and resilient. My advice is to choose those moments wisely. If, like in your situation, you feel you and that person have a lot in common or appear to be clicking, then why not take the shot? Take those risks sparingly, but take them.

It’s when people have no idea of what they can reasonably pull that they wind up frustrated and angry that nobody is returning their interest. The men and women you always hear complaining about their asshole dates or who frequently find themselves dealing with that person who texts but never wants to meet or people who fade in the middle of email exchanges? Those people are probably shooting out of their league the majority of the time. I can not stress enough the importance of knowing your audience. You will avoid so much aggravation if you correctly identify the people who like you and then try to like them back. If you don’t want to do that, then you must recalibrate your expectations and understand that getting that one amazing person you met will be atypically difficult. If you think they’re unique and special, I can assure you someone else does, too. You will likely be vying for their attention and interest. Learn it. Live it. Love it.

The only way you’re going to know what she thinks is if you contact her. She’ll either respond and be interested or she won’t. I would rather try and fail than always wonder what might have been. Just be honest with yourself of what you can offer in terms of time and interest.

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16 Responses to “When Is It Wise To Shoot Out Of Your League?”

  1. fuzzilla Says:

    It can kind of be forgiven in someone so young, but – OP, *do not* build people up in your head like that. You’ve only looked at this woman’s profile and have nothing else to go on.

    Send her a nice note, 4-5 friendly sentences referencing something in her profile, something cute to get the conversational ball rolling like asking where one of her vacation shots was taken at or if she’s ever tried a certain restaurant or something. Then forget all about her unless she writes back. Treat it like buying a lottery ticket. Then message like 10 other women with the same approach while you’re at it. The Pick Up Artist community would say, “Don’t get oneitis,” which is a concept I actually agree with. Especially with someone who’s only pixels on a computer screen at this point.

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  2. DatingNoob Says:

    Why is it that so much advice and analysis always starts with the concept of leagues? It is all so subjective and malleable that in the end it makes no difference.
    As for the OP, go for what you want but know that as you get older and begin your career, your options will only increase.
    Second, she is 28 and in her career, it is very possible she is actually looking to settle down and have children(My assumption is that Midwest women are more traditional than at least those of NYC). If not now, than very soon. Is that something you are open to?
    Lastly, don’t come to any conclusions until you at least meet her and get to know her. She may look great on paper, but disappoint in real life.

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    • Nicole Says:

      “Why is it that so much advice and analysis always starts with the concept of leagues? It is all so subjective and malleable that in the end it makes no difference.”

      Yes. This. Thank you for saying it so well.
      If we were all judging potential partners solely on looks (or on any other single, objective measure) the idea of knowing your league would make sense. But that’s not how it works, at least in my experience.

      Looks count, sure, but so do age, financial stability, personality, sense of humor, intelligence, availability, location… I could keep going forever. Everyone assigns different weights to these variables, developing their own unconscious calculus to evaluate prospective partners. Plus, we don’t all want the same things. A man wanting kids is a huge plus to some women, a deal-breaker for others.

      If someone ignores you or fades early, it might be because they think they’re out of your league… But you’ll never know which of the hundreds of potential factors caused them to decide this. I agree with Moxie’s point that if you’re not getting replies or dates, you’re looking at the wrong people… But trying to determine my “league” just seemed like an exercise in futility.

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      • C Says:

        This is sooooo true!! About 10 years ago, I was very insecure and avoided dating my roommate who was an amazing guy and complimented me and flirted with me regularly because I thought he was out of my league. One of the big mistakes I’ve made in my life. Before anyone says he just saw me as a hookup, at the time he was a pretty inexperienced young guy who strictly pursued LTRs.

        I also recently dated this goofy physicians assistant who I gave a chance to because he had a good sense of humor even though in my mind he was benieth me (i.e. my age and less intelligent, my height – so short, chubby, physically less attractive then me) and he immediately tried to FWB me. Apparently he ranked me benieth him.

        I’ve dated attractive and accomplished men who would only seriously date women if they were intelligent, had a college degree and were ambitious, others who would only seriously date women who were athletic and into the outdoors, and other men still who couldnt care less about either career ambition or physical activity level as long as she was nice and hot.

        Hot debate. What do you think? Thumb up 11 Thumb down 2

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      • DatingNoob Says:

        ” if you’re not getting replies or dates, you’re looking at the wrong people…”
        Sometimes. I say, you are most likely not aware of what the people you want are looking for and tailoring yourself to that. It’s amazing what a profile face lift and better pics can do or learning how to dress well for example.

        Like or Dislike: Thumb up 9 Thumb down 0

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    • LostSailor Says:

      It is all so subjective and malleable that in the end it makes no difference.

      It may be subjective and somewhat malleable on an indivicual level, sometimes, but it definitely makes a difference.

      C’s comment is a prime example that “leagues” exist. It’s also a prime example of the lament that they don’t, which usually translates into “I wish they didn’t exist!”

      Usually the undercurrent is “I tried to date someone who judged me negatively, why did they do that, this whole idea of “leauges’ is stupid, why didn’t they choose me…”

      The common thread is “not everyone is like that” (true, but enough people are as to not make a difference) and “why won’t people I’m really attracted to like me?”

      Sometimes generalizations like this are quite usefull. It’s really all a matter of, as Moxie says, knowing your audience. By all means, shoot beyond it, but recognize that it may not work out for predictable reasons, and don’t take it personally…

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      • Nicole Says:

        I understand what you’re saying, but I think we risk driving ourselves crazy if we automatically assume anyone who ignored or rejected us did so because they’re “out of our league”.

        I went about a dozen guys in their mid-30s who were cute, smart, funny, successful professionals. If anything, they should have been out of my league (money-wise, at least!) but it was me who said no thanks to all of them after 2 or 3 dates. Not because I didn’t think they were good enough for me… A couple because there was no chemistry, and most because they obviously wanted kids, and I don’t.

        I basically realized that between having been married before and not wanting kids, I’m unlikely to really connect with these never-married no-kids guys my own age. So I quit responding to them online. I sure hope they don’t readjust their perception of themselves when I ignore their messages… sometimes it’s really about individual stuff and not leagues.

        I guess that’s why I think it’s only worth analyzing the whole “what’s my league” thing if you’re seeing a real pattern of rejection. And to me, “know your audience” is as much about knowing what you’re looking for as it is anything else.

        Like or Dislike: Thumb up 7 Thumb down 1

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      • C Says:

        I’m not sure which comment of mine you were refering to.

        One guy tried to date me but i rejected him because I felt benieth him. I mention that because you can be rejected by someone not because you are benieth them, but because they feel benieth you.

        In another case, i gave a chance to a guy i thought was benieth me who similarly gave me a chance while feeling i was benieth him. How does that confirm leagues? I ended up shooting him down for a 3rd date at which point he said he was lukewarm too and we both joked about the whole thing.

        To some degree, there is the element of some market value. I probably dont have a shot with George Clooney and the next homeless guy who flirts with me is probably out of luck too, but Nicole said it much better than i did. Each individual person assigns different weight to different attributes, so you cant assume you are out of someones league unless you know their value system. There is also the issue of chemistry (as Nicole mentioned). Havent you ever found yourself very attracted to someone and you had no idea why as this person was completely not your type. Or havent you ever dated someone who was absolutely perfect in every way but kissing them was like kissing your sibling?

        Attraction is a complex enough thing that i wouldnt pigeon hole myself or anyone else.

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  3. D. Says:

    Ok, two things.

    First, the OP is 23. I’d say that is prime to for “trial and error” when it comes to dating. You’re just barely dating in the adult world, and that experience is further warped by existing in academia for at least the next two years (when your rotations begin, it’ll be a lot closer to life in the “real world,” or at least the real world of being a practicing physician). So, go ahead and give yourself permission to fuck up. Touch the hot stove. Tread on the thin ice. Poke the bear. Yes, you’ll get bruised and hurt, but if you can manage that without simultaneously becoming bitter, or supremely jaded, you can gain a ton of valuable experience from your mistakes. Far moreso than your successes, I’d add.

    Which brings me to my next point about “leagues.” I don’t actually think “leagues” exist, per se, at least in the kind of quasi-mathematical rank-ordering that a lot of people engage in. “Oh, you’re a 7. no way you’d pull a 10.” “What you fail to realize is that your market value is falling while that guy’s value is rising.” Yadda yadda blah. As if attraction can be quantified. Bullshit.

    That said, I think we know two things: (1) when something seems too good to be true, to the point where something just feels (or would’ve felt — if you’d been paying attention) “off” about the situation, and (2) the types of people to whom we are most likely to appeal.

    If you think that the person across the table from you is (A) someone that you wouldn’t normally appeal to, and (B) seems “too good to be true,” then you’re probably “shooting out of your league,” or rather ignoring stuff that you REALLY ought to be paying attention to, and you’re probably headed for a situation where you’re gonna get burned.

    The other thing that I think ends up happening sometimes is that, due either to a moment of spectacularly good luck early on in one’s dating career, or a deep-seated fear of actually risking one’s heart, people can end up “shooting out of their league,” or more accurately developing a warped sense of the types of people to whom they’re likely to appeal, which leads them to invest a lot of time and energy in dead-end scenarios, while simultaneously putting on blinders as to other people who might genuinely make them happy.

    But at 23, it’s entirely likely that you’re still figuring out a lot of that stuff anyway, so go out there, screw up, get burned, and learn from it. And have fun while you’re at it!

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  4. C Says:

    I was once the 28 year old who was approached by a 23 year old I worked with. What he had going for him is that I already knew him and he was a nice and cute young guy. You’ll have more trouble online in general.

    I agree that you should never get too excited or start thinking too many steps ahead with someone who

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    • C Says:

      …you have only looked at. Just realize a) that with online dating most people will not hear from MOST of the people they contact, and b) she may be nothing like her profile suggests when you meet in person so do be overly excited.

      Some women like younger men and some dont. It all really depends on her preferences.

      In my case, we went out twice and I lost interest. I wasnt really into younger guys. Although this kid was great, his primary fascination with me (other than a general physical attraction) was that I had by 28 achieved quite a bit of professional success that as a 23 year old college student he earned for. I probably would have been more interested had he not looked to me as more of a mentor than a partner. Treating her like an equal is your best bet. Although, I do know one women who always prefered dating younger men and loved being admired by them for her accomplishments…..so I suppose you should play it by ear.

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  5. LostSailor Says:

    Wait a sec. Alex “just sent a message to a woman” on OKC, and he’s already second-guessing himself? He never says that she responded or didn’t respond, so isn’t this putting the cart before the horse?

    He seems to have already spun out a first date, rejection, self-doubt about a relationship, and his “situation” all before we even know if she even responded to his initial message.

    Dude, wait until you have an actual live woman sitting with you in a bar for a first drink before you start down this road. You’re 23 and already worrying about relationships with women who you haven’t even met yet. Relax!

    That said, whether Alex might find success with a woman 5-years older depends mostly on his maturity. It’s a good point that they’re both in the medical profession, but his worrying about a non-existent “relationship” doesn’t bode well.

    Alex, you shouldn’t obsess over anyone, but especially before you meet them.

    But to the larger question under discussion, yes, there are “leagues.” They are fluid and somewhat subjective, but they are real, based on perceived social standing, looks, money, etc. They are not rigid categories and there are always exceptions, but they exist. And I’m a firm believer in sometimes shooting out of one’s league as long as one has realistic expectation that it might not work out well if at all. You need to have a thicker skin and not take rejection personally, but you never know when you’ll find one of those exceptions.

    Moxie is right that dating success if one is good at identifying the right audience (and spare the exclamations of “that’s settling! Never!), but you always miss the shots you never take…

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    • toffee Says:

      I agree with LostSailor. No one knows what’s going to happen after sending just one message. She might reply to indicate her interest, or she might not. Even if it’s the former, it’s still a long way away from a real relationship. OP is jumping the gun here, I feel, which is unfortunately all too common and a normal thing to do when you’re just trying figure out how the whole dating thing is supposed to work.

      In the past, if I came across a profile that was witty or well-written with great photos, I would get fixated that the guy was going to be “The One” and my hunt for “The One’ would be over. (yup I’m a woman) However, oftentimes the attraction fizzles when we meet up and he’s not who i imagined/assumed he was going to be. It’s only with time and experience that I got over myself and just DATE with no agenda other than to figure out if the guy on the other side of the computer is good fit for me. That’s all online dating is. At the initial stages anyway…

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      • fuzzilla Says:

        I totally used to do the build them up in my head thing, too, and it’s bitten me in the ass many times. Still to this day I have to consciously remind myself to base my opinion of someone on their behavior, on things they actually did and said. Anything else is just hope and lust and wishful thinking and a ticket to madness. Nothing wrong with a little hope to keep the engine running, but keep it in perspective.

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        • toffee Says:

          “…Anything else is just hope and lust and wishful thinking and a ticket to madness.”

          Well-said! ;)

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  6. Bogey44 Says:

    I’m 24, so I get where the OP is coming from. Just a couple of points to expand upon…

    1) OP, it sounds like you’re building this woman up in your head based not on anything she’s actually done, but rather your perceptions of her and what you want her to be. Don’t do this. I’ve done it in the past and it almost always leads to disappointment. It also shows a lack of confidence and can seep into your interactions which will sabotage your chances. Someone else referenced the PUA concept of “one-itis” and that is one of the best things to come out of PUA. You can’t value someone or something unless it has proven it’s value to you, so take your shot and then forget about it.

    2) Don’t get too hung up on the age difference and certainly don’t reference it in your message to her. If you did this you’ve already lost. Again, it shows a lack of confidence. If you put the idea out there that she may have a problem with you being younger than her then she will have a problem with it. You never want to build an “out” into your initial contact, whether online or in person. OKCupid has the “I’m Looking For” section with desired age ranges, relationship types, etc that everyone must fill out. Since you didn’t reference it in your original post I’d be interested to hear what she put there and how you matched up. If her desired age range was 30-40 you probably don’t have a shot, but if it was 25-35 you could be okay depending on other factors. What about the relationship type she’s looking for? Is it the same as yours? Did she list anything under her desire to have children, and if so how does that match up with what you have listed?

    3) As far as the concept of leagues, they exist but they are fluid and they vary from person to person. Honestly, this is something that online dating simplifies because you have some insight as to what the person values before deciding whether or not to take the plunge. What age range are they looking for? What type of relationship are they looking for? And what words have they used to describe what they want in a potential match? For example, if they mention that they like tall men and you’re only 5’7″ you’re probably not in the same league, regardless of what else you may have going for you. All that being said, the most important thing is to identify what it is you want and tailor your profile towards achieving that goal, that way you can signal to potential matches that you are on the same page in this regard. As far as actual attractiveness, there is some flexibility here. True a “2” is never going to become a “9” (I hate the 10-point scale, btw), but if you get in shape, dress well, take good photos, have interesting and diverse hobbies, a decent job or career prospects, and carry yourself with confidence you can overcome some physical limitations. The important thing is to have a relatively clear idea of what types of people you’d be compatible with and how to convey that compatibility rather than judge your “league” on looks alone.

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