Super Awkward Crush

[IthilienDude]

Hello all! Thank you in advance for taking the time to help me out.

First off, talking about these things fills me with all the embarrassment/shame feels, but that's not a discussion for here: I'm just terrible at talking about dating and stuff :3

So, I've had this very good friend for about 4 years. He and I have a good friendships, have slagged each other about our awful choices in past partners, but have always taken care of one another. We met through a friend, and only ever used to meet through that friend, but now have a friendship in our right and chat online almost every day until late at night. We've had disagreements, of course, but have always recovered. Recently, I've developed a little crush on him, which is funny because I've never even looked at him like that before. Over the past few months, I've come to be very fond of him. We were out together over the weekend, and had a marvelous time! We both flirt like mad, but we're both very flirty people anyway so that doesn't really mean much now I think of it.

All sounds lovely. HOWEVER, there are a few detractors. He lives about 2 1/2 hours from me, he is almost 10 years older than me, and has a hopeless unrequited crush on a woman that he hooked up with one time; he also is quite active on dating websites, so I don't feel like I have a look in here. Also, we're both part of a very well established group of friends. Even though people take the mick out of us for being so flirty and suggestive, and many people have commented on the fact that "Wouldn't they make a lovely couple?", I think everyone would be genuinely shocked if we got together. It'd probably completely change the dynamic of our social circle. Part of me -- albeit the part of me that overthinks things -- is full of the 'fear of missing out' if I go out with this guy.

Basically, I'm full of confuse and have no idea what to do next.

[Sam W]

Hi ithiliendude,

Glad to see you again!

Crushes can be such tricky beasts. A crush can be enjoyable to have for fantasy or mild flirting purposes, but those feelings don't always translate into a good relationship, and it sounds like that's partly why you're feeling mixed up. From what you've described the biggest warning sign to me (after the age difference, as that can be an issue for big and little reasons) is that this guy is still hung up on on a past partner. Generally, when that's the case, you end up feeling as though you're always being compared (and can never live up to) another person. Not the best foundation for a healthy and happy relationship, you know?

Something that might be helpful is to think about the traits that you find appealing in this friend. Then keep that list in the back of your mind if/when you're looking for people to date. A crush may not always be a good partner for us, but they can often be a window into the things we're looking for from a partner.

[IthilienDude]

Thank you for your response,

I think for me the reason that he has become attractive to me is that we have a good foundation of friendship: we confide in one another about life in general, our very disastrous dating lives, but also he helped me a lot when I was suffering from depression. Like, he's one of only a very small handful of people that would know about my past abuse (and me about his); he knows more than my own mother does. We have an affectionate friendship, too, which I only have with a few woman friends, and extremely rarely would I be affectionate with male friends.

Where he lives is pretty remote, and opportunities for meeting people are very infrequent, so when he finds a girl he likes he tends to stick at the crushes/relationships until they're way passed their sell-by dates. I've known him for years: it's something he does and it bugs the Hell out of all of us (our social circle). Of course this is no excuse, but I understand why he does it. He's also overly loyal to women who mess him about, which is another one of his major flaws.

The only thing that puts me off the idea of pursuing it is how it would affect our social circle. I'm not worried so much about things getting weird between he and I, just how weird it would make it for everyone else. Like, if he were just some guy I knew aside from my friends, I'd probably be totally alright with chancing it.

(Out of curiosity, what reservations do you have about age gaps? For context: all of my closest friends are AT LEAST 8 years older than me, men and women alike, except for one friend who is nearly 5 years younger than me, who I know pretty much only through being involved in politics.)

[Sam W]

It sounds like he's someone you trust and feel really comfortable with, which is great! And I will say that it's not uncommon for that kind of connection to morph into a romantic attraction. One thing to think about is if you know his habit of getting hung up on girls he likes or dates, if you did end up dating him you could very easily find yourself on the receiving end of that a little ways on. Whether or not that sounds appealing to you is definitely something to include in the equation when you're weighing whether or not to try and move this from a crush to a formal relationship. Too, I think your concerns about what it might do to your friend group are sound. Dating within a friend group can change the dynamics (as can breaking up in a friend group). Now, social circles are flexible and adaptable, and many survive relationships between their members, but it can sometimes make things awkward for a bit.

With the age gap, I tend to react to them as read flags out of experience doing this work. You see a lot of older dudes seeking out younger women to date because they're less experienced at spotting the older guys' BS/toxicity. Now, it's less of a red flag if it's a 24 year old and a 34 year old then, say, a 26 year old and a sixteen year old. But a decade difference can still mean a mismatch in terms of where people are in life. That's not to say that some couples with age gaps aren't perfectly happy. That kind of dynamic can work, depending on the people involved and what they each want from the relationship.

You mentioned you and he flirt a bit. Beyond that, has he given you much indication that he's open to something more in terms of a romantic relationship?

[IthilienDude]

Yeah I've been thinking about that too: could I be the object of someone's affection if they're that attached to me? He's always gone for women are emotionally unavailable for manipulative, and I think his level of 'clinginess' -- to use a horrible term -- is directly proportionate to the level of security with those women. He tends to go for slightly older women with children, for some reason too, and he's stuck in this cycle of going for unavailable women, or complete strangers. But, when it comes to dating, I like to cross bridges as I get to them, instead of overwhelming myself with 'what ifs', because there was a time where -- because of my anxiety -- thinking too far ahead would give me panic attacks, and in extreme cases suicidal thoughts. (Don't worry: the counselor took care of that for me.)

I've watched him go through relationships (we've known each other roughly 4/5 years), and I don't see him as someone who manipulates to get what he wants in such and extreme/abusive way. Sure, he's not the world's most emotionally mature person -- he gets quite anxious in social situations, and in dating situations. Also, as I mentioned before, he tends to go for slightly older women, or women around his own age, so he doesn't have a track record of 'creeping' on younger women.... that I know of... (JK).

(incidentally, I'm 25, and he's 34. He's a very youthful 34, though, he'd easily pass for someone in their late 20s)

No clear indication, no, I will say that. I completely understand that at the moment it's on my side of things. We hug, we break the touch barrier very often, we make very suggestive comments to one another when we're having a laugh (all in good humour), he's told me on several occasions that he thinks I'm very attractive and compliments my style often, and he mentions that he likes hanging out and always expresses a wish to see me again when I leave, but there's been no actual discussion of it as something that could actually happen; it's all friendly banter from what I gather, and generally speaking he is rather gentlemanly.

Having said that, he makes sure to reassure me that he corrects people who think we were a couple. For example, we went to a club recently, and each time a guy came over to him to apologise for 'hitting on his girlfriend' (ie. me), he'd come over and tell me about it and make sure to include "Don't worry, I told him we were just friends." He also would do that on social media. I don't know if that's a subtle hint of 'I'm totally not interested', or him assuming that I need the reassurance that he isn't just being friends with me to get with me. I'm not sure, I'd only know if I asked him directly, which I don't think is wise.

Overall, it's left me in a strange headspace.

[Heather]

Honestly, what I am personally hearing about this person throughout all your posts is that you have feelings for them, but a giant pile of things make it seem awfully unlikely that a romantic relationship with them would be something positive or beneficial unless some of those things changed with him first. At the very least, I'd personally suggest having some big talks about these things if you decide to pursue a dating relationship with him.

To review the things I'm seeing you mention that make that so clear to me, you've said that he:
• "has a hopeless unrequited crush" on someone else
• has some bad patterns in dating, like only pursuing relationships with people who aren't emotionally available
• is very insecure in relationships
• doesn't strike you as having maturity, despite being in his mid-thirties
• struggles with anxiety in dating

That just seems like a lot of barriers or negatives to me, so I'd at least think about them and, again, should you decide to pursue this, talk about them together. But I'd also put in a strong vote that you hold up on pursuing anything with him at least until he seems to be over this other person. There's not going to be room for you until he is.

[IthilienDude]

Thank you for your response, Heather!

Yes, I have considered these things, and they all seem like serious detractors when they're laid out like that. I could give a counter to each one of those, but I realise I'm here for a good impartial viewpoint.

From a personal perspective -- as I've spoken about in a few of my previous threads -- I have difficulty with making 'friendships' within my relationships. I find that when I find someone attractive, I have a tendency to skip the friendships stage for some reason. In my life so far, my partners and my friendships have been mutually exclusive. Having said that, I had one boyfriend who'd been my friend for years beforehand, and when we dated we realised it wouldn't work out, it ended, we didn't talk for a while, but then went back to being as good friends as we'd been beforehand. In retrospect, that was probably the best romantic relationship I've ever had because of how non-catastrophic it was.

The point I'm trying to make is that I've had very few relationships that have come from a place of friendship, they've always had that romantic premise. In the process of getting to know the partner, most of the time I've realised that I didn't really like them that much as friends, but had romantic feelings towards them. The break ups were always monumentally destructive, and there was always months and months of dissolution because we didn't understand each other on a basic interpersonal level. I've always wondered -- since that ex that I was friends with -- if developing romantic connexions from friendships is ultimately a better idea than just being on the 'dating' scene. I know one could argue that that means in future, if I meet someone I'm interested in, I should have the patience to develop a friendship with them beforehand; that has occurred to me.

I just feel very jaded with the dating scene at this point though: I've been through the mill too many times, and have ended up in my mid-20s with nothing but a history of abusive ex-boyfriends who eluded my better judgment. I had pretty much decided I was done with dating for the rest of time until I started having feelings for this friend, to be honest. My own words to him in one of our last conversations about our respective tragic dating lives was 'It'd take someone fairly effing exceptional to get me interested in dating again' =P

I am the master of stewing in my own thought. These things always seem like a bigger deal to me than they really are. I find it difficult to be 'cool' about dating: when I was growing up, I was kinda expected to be looking for husband material from the word go, and meeting up with guys and just taking things a step at a time wasn't a value I was reared with.

Man, this conversation just got really depressing really quickly.

[Heather]

Well, it's on you, obviously, to decide if you want to keep dating or not.

But one thing I would say is that it's pretty unusual in my experience -- and certainly in my own life! -- to be "done" with dating by one's 20s in the respect that voila, you find one person you're then with for always and always and never date again. What's more common is for people to still be dating even through their 20s, often beyond, and even if and when a person settles down in one way or another with a partner for years, sometimes they'll find themselves again dating later in life.

I'd also say that having a few doozies, at least, when dating is pretty common. Having all of those be abusive relationships is a bit less so, but once we're talking ongoing relationships, we're not really talking about dating anymore, you know? Did any of this abuse happen when you were ONLY dating, or only once you pursued dating relationships as longer-term relationships?

I guess I'd also throw out there that trying some dating with people where you're friends first sounds like a good plan to me. But I also don't think that means that you will want to try that with anyone and everyone you're crushing on, especially anyone where it's clear from the start, or seems clear, isn't likely someone really open to dating in the first place, or who you know probably isn't going to be someone you'll have a great romantic or sexual relationship with, friend or not. Know what I mean?

[IthilienDude]

I do know what you mean.

I'm possible the least patient person I have ever met, and I've known me my whole life so that sets the bar pretty high! When things fail consistently, sometimes I just to throw in the towel completely. Like, I've been a singer my whole life -- since before I could talk -- and after one lousy band project I was involved in I didn't sing for a few months because I was so sick of it. After my bad experiences in art school, even though I'd drawn since I could hold a pencil, I didn't draw for 4 years because the thought of drawing one bad picture was too much for me.

I had one assault encounter with someone I'd been dating fairly casually for about 4 weeks, and had three ongoing abusive relationships varying between 6 and 18 months in length. I don't know if that answers your question or not.

What I said earlier wasn't trying to be a 'I was never going to date again, then he fixed it all' kinda comment, it was more of an indication of how I have become more emotionally available recently. It was just a funny coincidence how the person I have whinge-fests with about my disastrous love life to has ended up being someone I'm attracted to.

I do also understand that not all crushes could, or should, lead to relationships. I've been in the situation many times before where I've had a crush that I've just let slide because the person was totally unsuitable. I can do it, and it is necessary, albeit frustrating. My mind in these situations splits completely down the middle into "You only live once so carpe diem!" and "Sometimes in life you gotta let some things go", and at the end of the day, both camps are right for very different reasons.

I sometimes wish I was better at throwing caution to the wind: I'm a sordid perfectionist. I spent ages on the fence over things because I'm waiting for things to be juuuuuuuuust right before acting.... there has been a lot of doing nothing in my life on account of having this perfectionism.

[Heather]

You know, this:

When things fail consistently, sometimes I just to throw in the towel completely. Like, I've been a singer my whole life -- since before I could talk -- and after one lousy band project I was involved in I didn't sing for a few months because I was so sick of it. After my bad experiences in art school, even though I'd drawn since I could hold a pencil, I didn't draw for 4 years because the thought of drawing one bad picture was too much for me.

...certainly sounds like a kind of pattern worth breaking, about anything it plays a part in. because look, with those two examples, at what it meant you had to lose from your life that you enjoyed because you are going about life and its experiences as being about only failing or succeeding? Perhaps working on changing that with dating could be a nice gateway to changing it in all the parts of your life, so that bummers about "failing," or things taking more patience won't have to keep you from things you love or could love, you know?

Perfectionism really is a soul-crusher and a killer-of-joy-in-life. I know that personally, burning mine the hell DOWN has been something I've been working on for most of my adult life, and I'll tel you, the more of it I can kill with fire, the better my life and the way I experience it gets.

I hear you on the other bits: sorry I lost the plot a bit there.

It was just a funny coincidence how the person I have whinge-fests with about my disastrous love life to has ended up being someone I'm attracted to.

IME, not really. I mean, talking to people candidly and without filtering ourselves overmuch about our sexual or romantic history is a pretty intimate thing for a lot of people, a thing that usually tends to build intimacy. And attraction, be it sexual or romantic, is something that builds for most people most of the time, based on things like experiences of emotional intimacy, rather than both being all WHAMMO from the front.

[IthilienDude]

Oh I recognise that, and I'm doing my best to break it. I'm doing my best to allow myself to fail miserably and make an idiot of myself occasionally. When I was very, very, very anxious and had suicidal depression, any social faux-pas was world-ending. I asked a guy out once and he said no and I felt like pelting myself off the bridge, like; I did not take embarrassment well. At this point in life, the way I stop myself from freaking out like this is by repeating the mantra "Anything, even making an absolute moron of yourself and losing all your friends, is better than being dead."

I come from a high-achieving, pressure fueled family where nothing is lighthearted or fun: even at family gatherings when we play board games it's a fight to the death. My mother has to win everything, and will spend hours grinding everyone into the floor and lording her victories over the other family members. So as an adult, if I can't be perfect I won't bother at all.

I'm really bad for this in relationships: I'm too busy doing the whole perfect girlfriend thing that I completely sacrifice true vulnerability and intimacy. I do anything I'm asked and adhere to all social expectations of women in relationships, which builds walls so high that NO-ONE can get over them. After my last relationship failure, I at last realised that this was something I did, and it completely shattered my image of myself; I had no idea who I was for months.

Now, after all that, I'm beginning to think that I need to have the same level of openness and no-effs-given attitude that I have with my friends, but with my boyfriends/girlfriends too. I need to understand that relationships are about respect and understanding and compromise, just two people being who they are, but together. But, this does kinda mean I have to relearn how to do the whole dating thing.

But long story short, the reason I bring up perfectionism is that now that I'm aware of my behaviour -- and I mean hyperaware -- it bugs me even more. When I didn't know how much of a barrier it was, I was living in not-so-blissful ignorance. So now, when I'm trying to weigh up potential partners, the perfectionist part of me is like "Not this one: the next boy will probably be better", but if I keep doing that forever, I'll be single forever. This means that when I doubt, I wonder is it my perfectionism speaking, or common sense. That's why this scenario is so annoying: there are so many reasons why it could be really really good, and so many reasons why is could really really bad :/

[Heather]

Now, after all that, I'm beginning to think that I need to have the same level of openness and no-effs-given attitude that I have with my friends, but with my boyfriends/girlfriends too. I need to understand that relationships are about respect and understanding and compromise, just two people being who they are, but together.

This is the kind of thing to write down and pin up somewhere. This seems like an excellent mantra for you going back into dating. Nicely done.

[Heather]

Per this scenario, I think that if this person isn't even interested in dating you, none of what you're trying to decide really matters, so if you do feel like you're on the fence, one option is for you to ask if this person has that kind of interest, too, and then if they do, you can talk about some of your concerns from the front.

OR, you can just think about this for yourself some more. But I don't think concerns with this person and dating them are about perfectionism: I would be concerned about all those things I listed up there above, and I'm someone who will try nearly anything once, so.