Shy and Unlucky in Love
December 18, 2012 5:27 PM   Subscribe

Help me figure out why I'm so unlucky with romance

Yes, sorry, another question on this familiar topic. But of course, slightly different.

I'm female, almost 34 (but look younger and with lots of younger friends, if that is somehow relevant).

I'm shy but can be friendly, have a decent amount of friends, people tell me I am kind.

Appearance-wise, well, on a good day i think I look cute. I work out almost every single day, I take care of myself. I'm not a fashion maven and don't wear much makeup but I like to choose flattering clothes and sometimes enjoy putting outfits together. So, Ido n't think a hideous appearance is standing in the way...

But there is something going on here. I've had no long-term relationships, just flings with very unsuitable guys (one who was gay, one who was uneducated and untrustworthy, one who was just not on the same page as me.)

I know the no long-term relationship yet is not that big a deal. In some ways I choose that because I am independent and enjoy spending time alone.

I have quite a few male friends...and in the past I have expressed interest in a couple and they didn't return it. This just happened...with a guy I thought had been vibing on me...he happily told me today he has a new girlfriend. I told him how I felt (to explain why I didn't think we could hang out anymore) and he said he only liked me as a friend). I was crushed. This happened before, a few years ago, the same thing, and I was devasted then and afterwards became afraid to tell guys if I liked them.

A friend gave me the feedback that I am shy and hard to get close to so guys don't think I am interested.And a lot of timesI am not interested at first because it takes me time to get to know someone.But how do I change that?

Or else there is something else about me? What is it? Or how do I figure it out? I do want to love someone and be in a relationship but it never seems to happen.

There have been guys who have expressed interest, but they all just seemed...not right.

Sometimes i think that I only like guys who are not right for me.

Does this sound familiar to anyone? I'd really appreciate any advice at all. I am really hurting.
posted by anonymous to Human Relations (26 answers total) 9 users marked this as a favorite
Hrm. First off, sympathy. You sound neat.

Second, my first instinct is always to do a nice critical analysis of how your parents trained you, good and bad, and see what flaws/bad ideas you may have absorbed from that.

Third, try dating just to date? Don;t go into it with any expectations, hopes, etc. Just go to have fun, hang with interesting people in an EXPRESSLY possibility for romance situation, and see what happens. Don't date jerks or people with red flags, but just explore lots of different people.

If you want to be analytical, see how people flirt, and find a style that works for you.

Where do you meet said guys?

I think maybe guys often put ladies in the 'friend zone' too. If their first few hints/signals/whatever get ignored or unintentionally rebuffed, I suspect they would shut down that avenue of pursuit.

Ok, I lied: My first first instinct is always: Do you like yourself? Do you love yourself? Who or what says 'i'm not good enough' to you?
posted by Jacen at 5:53 PM on December 18, 2012 [1 favorite]

One of the upsides about online dating is that it's already on the table that both people are looking for dates.
posted by Sidhedevil at 5:56 PM on December 18, 2012 [7 favorites]

Agree with both Sidhe and Jacen. The website Little Red Rails is a good introduction to online dating. One thing that he recommends is intentionally dating multiple people at a time (taking care not to go overboard on this, of course), in order to become more comfortable with dating. Based on your description we seem somewhat similar (only I'm male with a number of non-romantic female friends), and this advice has been helpful for me.
posted by lharmon at 6:03 PM on December 18, 2012 [2 favorites]

Have you asked your male (or, for that matter, your female) friends if they have any friends that they think might be a good fit for you? This doesn't work for everyone, and it might not work for you, but I know people who were introduced by mutual friends and had happy relationships as a result.

I think you need to look at your expectations a little. You say yourself that you've had flings with completely unsuitable guys, but then you also reject other guys for being not quite right. I'm not going to armchair psychoanalyze you, but you might want to think about why you are rejecting the guys who might work for a LTR and going for the guys who won't.

Seconding dating sites. Please (speaking here as a formerly single guy), get a good picture of yourself that doesn't include (a) your girlfriends (I really don't want to guess which one is you) or (b) male friends.
posted by It's Never Lurgi at 6:12 PM on December 18, 2012 [1 favorite]

Hi, I am you too. I have never had a long-term relationship as an adult either, despite very much wanting one.

I would also say to try online dating, but with an emphasis on you contacting the guys you're interested in rather than waiting for a suitable handful to contact you. That way you know you're getting the "right" ones rather than investing in guys who are just after the chase. If you don't initiate, you might end up with an inbox mostly full of guys who have expressed interest, but they all just seem...not right and that will make you wonder if there's something wrong with you just like you're wondering now. (Hint: there's not! You just need to broaden your selection pool.)
posted by houndsoflove at 6:21 PM on December 18, 2012 [5 favorites]

This is why online dating was invented. Try it.
posted by John Cohen at 7:09 PM on December 18, 2012

also as a 34 year old guy new to online dating (ok cupid style), the very fact of a woman reaching out is enough to get extra attention.
posted by garlic at 7:21 PM on December 18, 2012

Perhaps you need to learn to flirt, so that guys start wondering about you as a possible romantic partner earlier on. Light flirting is acceptable in most social circles even if you aren't yet sure whether you are seriously interested in the person, too, so even if it takes you a while to decide you are attracted to the person, you can have started a little flirting before that point.
posted by lollusc at 7:23 PM on December 18, 2012

I've had no long-term relationships, just flings with very unsuitable guys

You need to go out with some suitable guys - then a longer term relationship becomes a possibility.

I was crushed. This happened before, a few years ago, the same thing, and I was devasted

It is hard for a shy person to do this sort of thing - when you like someone, you want them to like you, and it's hard to handle when they don't. You need to work on not caring so much [yes, this is an attribute of confidence]. Think of it as their failing, not yours. But whatever you do, don't let some knockbacks put you off trying - it happens to everyone, there will be suitable people who like you, but if you stop looking, you won't find them.

Or else there is something else about me? What is it?

We can't possibly know this unfortunately. You sound like a nice person - I wish you luck.
posted by HiroProtagonist at 7:26 PM on December 18, 2012 [2 favorites]

I have personally hated online dating because wading through that is about 100x worse than dating IRL - it just reminds me how many people I'm not suited to, which feels even worse.

So my suggestion would be common interests. Choose a hobby or class or volunteer group or whatever floats your boat. Something where you get to spend time with people, building up that rapport, on an on-going basis. That allows you room to get to know people, but also provides a buffer because you're not solely there to meet guys.

Although I know people who've hooked up in a bar one night and gone on to get married, a lot of LTR start at a gym or in a class or through sports/hobbies or through their friends/family.
posted by heyjude at 7:47 PM on December 18, 2012 [4 favorites]

I have always loved volunteering because you have plenty of time to spend with someone, it's a structured situation so you don't have to be great at introductions and small talk, and you have something to talk about. It really gets you over that hump of feeling like you just can't get close enough to anyone to know whether you like one another.
posted by Miko at 8:01 PM on December 18, 2012

At least you've got integrity -- so many get into something (anything, really) and stay in it out of the fear of being alone at the holidaze. They don't want to sing about dashing sleighs by themselves.

You could so easily be with someone. Just settle, grab hold of the next set of eyes that seek to hold yours, settle for someone who is not the right fit, so's you can have someone to sing with. Even though his singing drives you sortof berserk...


Are you perhaps afraid to do this, to be with someone? Not consciously, but under it all. Which won't be easy to see -- esp for you to see, unaided, without help -- but sometimes in the trails we leave behind us we can see patterns, nothing walks on aimless feet, etc and etc.
This part of my response is of course is The Therapy Answer which by law has to appear in every AskMe that's about relationship issues.


So many people just luck into it. I mean, I'm glad for them and all, but sometimes I just hope their legs grow together, I just really do.


Don't forget the "half age plus seven relationship rule" because no one else has forgotten it. Are you closed off to dating that guy who's forty-one years old? He really cares about you, probably he's thinking of you right now, his arms empty for wanting you in them.


Last. My Aunt Billy. Beulah. She married a jerk, had the jam to divorce him back when only people in New York City or Hollywood got divorced, married this super great guy -- Ted. They were together long years, good years. And then cancer nailed Ted. And my Aunt Billy grieved him but she was not going to be alone. And she set out to prove that.

She'd have fit right in with those psycho's on their crusades, lo those centuries ago, not that she was on a horse or tortured anyone (except maybe for the guys who she rejected after a date or three-- she was a pure beauty and absolutely a live wire) and she didn't carry bibles or whatever those clowns did back then but man oh man was she a crusader in her cause. She was willing to take the chances, again and again she put herself out there -- I doubt she kissed any toads but I know for a fact she went on some dates with a few of them, as she sought.

She hit the jackpot. Vern. What a great guy! We all loved him and he sure loved us and oh man did he ever love my Aunt Billy.

She's gone from the scene now, she's maybe ten years in the grave, but that doesn't mean you can't tap into your very own Aunt Billy energy, put some Aunt Billy type shoes on your pretty feet and go and kick some serious butt same like she did, and don't you ever even think of kissing a toad. You're an attractive woman, a sharp dresser, fit and healthy, you write well, you seem alert. You're a catch. Take my Aunt Billy with you, maybe, on a date, ask her "Hey, is this guy a roach, or what?" and who knows, maybe she'll give you a sign, and give you the nod when the right one shows up.

He's going to show up. I bet he's going to show up.

I hope so, for his sake -- you sound like a fine woman.

Good luck.
posted by dancestoblue at 9:24 PM on December 18, 2012 [12 favorites]

I second going out with an older guy.

I think that as a woman dating in her 30's, sometimes a little bit of insecurity about aging comes in (I mention this because you wrote that you look younger for your age)... but you're always young to someone.

After my last relationship I decided that I wanted something completely different. (I'm 31 btw) I decided to go for someone older as a conscious choice. I wanted someone was married before, but not just coming out of a divorce, it was okay if he had kids, but I preferred them older so that there wasn't any manipulative stuff going on from the ex partner... and I felt by enlarging my prospective pool of men would give me a ton more choices... and it really really did... and I don't have to compete with a ton of other chicks my age or younger...

and I totally hit the jackpot.

New man is 44, super sweet, stable, wants a life partner, is great in bed, and really really knows himself... there are no mixed messages and it isn't gamey.

I couldn't be happier. I recommend it highly!
posted by misspony at 2:11 AM on December 19, 2012 [5 favorites]

Consider nipping your crushes in the bud and getting it out in the open, and if it's a no from the guy in question - move on. I'm not clear on whether you let the crushes continue until you get hooked on the idea of a guy but to me it's clear that the devastation you feel afterwards means that you are deeply invested in the idea of your crushee.

It's hard to be courageous in this regard when you are shy, but do consider just acting on/dealing with your crushes swiftly before they have the chance to hurt you too much. Life's too short etc etc.

Therapy etc, but if I can just say, the best lesson I learned from my therapy person re: relationships was that it is important for you to state your minimum terms of the agreement upfront so the other party knows what is expected of them and is given the opportunity to say yes or no without pressure or punishment. That sounds contract-y I know but it's a sound idea. Sub-lesson: you need to give the other person room to say no (or they feel pressure or that they will be punished). Example! When dating my current SO who was not so great at being in relationships when we first started going out, had a habit of making me feel not so great. After quietly tolerating it to see how things would pan out, I approached him and said "Ahoy. When you do A, B and C, it has the effect of making me feel like dirt. I would like to keep doing this but it means that I need D, E and F. If you can't do this it's okay, I'll be sad but I'll also be fine. Call me when you've had a think." (And kerblammo, still together after 2 years and it's going strong).

It won't always go your way but at least you'll know and can move on. The one condition of this whole thing working is that you need to be okay within yourself to hearing no. I think if you can't others are more likely to be able to sense it.

Other excellent therapy lesson: the more you invest in a hypothetical, the more it occupies and devastates you if it doesn't come true. It's not about stopping yourself from caring at all, but it's about giving everyone (yourself included) room to say or hear no. And then it won't hurt so much. And if you just nip the crush in the bud, that'll help stop you from obsessing over it. You're putting a lot of pressure on yourself to achieve an LTR, and it hurts you if you see yourself as failing. Consider a change in how you see and value your desire for this sort of relationship. Consider what your expectations are in a relationship and let the other person know gently with as little pressure as you can muster. A no is just a yes to something else. (that was very new age-y of me, apologies).

FWIW, you sound like a totally crushable, loveable person.
posted by scuza at 4:12 AM on December 19, 2012 [3 favorites]

I have a good friend who was in a similar situation to you. She had tried online dating but kept meeting unsuitable guys. She had asked friends to set her up with dates. Nothing worked. One day she asked me to take a look at her profile. And she clearly had no idea who she was.

My awesome friend is a scatterbrained girly girl. She reads romance/fantasy novels, listens to mainstream pop, loves to cook in her cluttered kitchen, adores her two cats and works in a semi-creative job. And she was looking for a well-educated, high-flying CEO type to take her to the opera and on weekend trips to Paris/New York. This may work out in romance novels, but in real life my friend kept going on very short dates with guys who blew her off once they realised she was completely different to what her profile said she was.

Long story short, here's my advice: if you are trying out online dating make sure that you have a good friend to look over your profile. Make sure you are completely honest with yourself about what you are looking for. What's important to you? I am not talking about a guy's salary level or his hair colour - but intrinsic values. And what are you bringing to the table? Who are you (apart from being shy and looking okay)?

And I second dancestoblue's words that it's entirely possible that you may be afraid to get hurt that you are rejecting suitable partners without even realising it.

Sit down and have a really good, long look at yourself. And then put yourself out there. You sound lovely!
posted by kariebookish at 4:17 AM on December 19, 2012 [2 favorites]

Just to add to my last thing - I think the investment in certain crushes that lead nowhere (eventually) means the hurt is felt more acutely and thus the feeling of being unlucky follows. It just hasn't happened for you yet, that's okay. It's not because you are somehow wrong.

Also re: being scared to tell guys you like them, I think it's cool and brave to make yourself vulnerable, and know that if it doesn't work out the way you want that you are a strong person who can get past it. People can sense that sort of confidence. It is okay if things don't work out. It doesn't mean you're a failure.
posted by scuza at 4:22 AM on December 19, 2012 [1 favorite]

Crushes are your enemy. If you find yourself liking someone, you should tell them so. So what if you get rejected? That's part of life, roll with it. It doesn't mean that you're a terrible person, it just means that your crush isn't into you. Isn't it better to get these things over with quickly? Before you invest time and emotions inappropriately?

Start thinking of yourself as a "happy-go-lucky" sort of a person. You love your friends, you love kittens and puppies and you like men. Let people feel the affection you have for the human race. That vibe is infectious, and people can't help but respond to it.

Crushes and relationships with inappropriate dudes indicate an ambivalence about relationships. You want to feel the love and affection, but you don't want to open yourself up to being hurt.

It sucks, but you're going to be hurt. That's the nature of the beast. But the good news is, you'll survive. Soon, on this journey, you'll meet a fellow traveller, and because you've learned to be open, and affectionate and to identify appropriate mates, you'll be in a healthy relationship that brings you and the world joy.

Everyone here knows, but I'll lay it down for you. I was picky and I waited and I was married 4 months before my 40th birthday.
posted by Ruthless Bunny at 5:43 AM on December 19, 2012

Your shyness is NOT why men aren't approaching you. Shy girls get approached.

Men are highly visual, just like many women. We are also reluctant to get "shot down" especially in front of others. We make a decision to approach based on how you look plus the chances of getting that positive response from you.

- When you go out, do not stick to your group the entire time
- daunting as it is, find a way to go out to social settings alone; you increase your chances of being approached
- smile naturally in these social venues
- stop asking any more of your guy friends out. Not only are you limiting your pool, this is a "tough hill to climb" once the friendship has set in.
- finally, this may be sensitive area, but it's the reality. What do you really look like? Is your "style" in line with the type of guy you are pursuing? You need to get outside opinions on this, close friends or through strangers. Appearance matters. Not all men think or work this way - but, many do.

All one man's opinion. Good luck.
posted by Kruger5 at 5:49 AM on December 19, 2012 [3 favorites]

Wow, you sound a lot like me!

I found that dating in one's thirties is reallllly hit or miss when it comes to meeting people whom you'd actually want a LTR with. I dated a lot of very unstable people, it's amazing who is out there.

With that said, what helped me relax and just be myself was to join a social sports/special interest group in my local area. It was really fun to get out and meet new people outside of my friends group. The fun part about this also was that the focus was on the activity, and not on anything related to dating.

...And that's where I met my boyfriend, who I now live with over a year later, plus one unruly cat.

You sound like a good person and the world needs more of those. I say focus on your interests and activities and things will fall into place.
posted by floweredfish at 6:34 AM on December 19, 2012

And a lot of timesI am not interested at first because it takes me time to get to know someone

This isn't uncommon, but I find it also something that the risk averse and the people who don't actually want a relationship tell themselves. It makes things easy-- you don't have to stick your neck out to flirt and go out on a date with someone you just met, and by the time you get to know them better, you can be assured that "the moment has passed" and won't lead to a romantic entanglement.

You pretty much have two options: one is to socialize and meet new people and be willing to flirt and go out on dates with people you only just met on the mere basis of "chemistry" and a couple of conversations. The other option is to be pretty aggressive about online dating, screening for your preferred features and meeting people in a context where the explicit point is to get to know someone better to see if dating is what you want.
posted by deanc at 6:45 AM on December 19, 2012 [1 favorite]

Getting into a relationship can be tricky. This thing you are talking about, the "I only like guys who are not right for me" thing is painfully common. A better way to frame this is that you are so far only attracted to men who: are independent, are well rounded enough to be pursued by other ladies, and who you feel comfortable with and know well. So that's fine.

I would avoid the direct tell when it comes to admitting crushes, and especially avoid it completely if it is just some kind of post mortem I liked you but now you're not available reveal. The trick is to start building yourself up in your own mind to be as cool as these dudes that you like. You do not need to tell anyone that you are crushing explicitly, there are tried and true rules for engagement that will help you calibrate the amount of interest that you are showing at any one time so that you leave enough space for the chase to happen.

The rules:
-Match investment. When you have a crush, try to make sure you are behaving in a way that is consistent with your crush in terms of how much effort they are expending.
-Open doors. Tell people you are interested in very small things about how you are spending your time to see if they ever express interest in tagging along. An invite or two from you would be good, but often it is very helpful to just give people an opportunity to express their own interest in something you are doing.
-Play it cool. Earnestness and sincerity are super great awesome things, but there is a time and a place for everything and people should not be given the key to your entire kingdom of vulnerability. Think about how you would like to be perceived: do you admire people that are extremely up front about their feelings? reserved? cool? open? Identify the behaviors that you think are attractive and make sure you are displaying them yourself.

Online dating is a thing you can do to practice, but if you don't like it don't sweat it.
posted by skrozidile at 7:09 AM on December 19, 2012 [2 favorites]

You need to get out of your head on this one really and stop beating yourself up. Unsuitable guys? yeah the gay one was properly unsuitable but the other two? Unless girls marry their first ever boyfrined, then they'll have an experience of break-up and that will be because of 'unsuitability'. For a lot of people that unsuitability might have come through trustworthiness (its not like its been long since i heard or read on here a tale about cheating) or not being on the same page (same thing again - he doesnt want to get married, he doesnt want to have kids, he wants to move to x, he doesnt want to work for a living, he wants to drink and smoke weed ebvery night, they are ALL over this place)

Focus on the future and the future means new. Some good advice here already - new experiences instead of crushing on friends, if you want to tell someone you like them do it before you get all invested in your crush so you dont get so sad (and dont waste time/energy on spending all your time with crush or trying to make crush happen even in subtle ways). Also dating - if you want to have a relationship this is a good way to maybe make that happen.

And yeah, maybe try some older guys (and also making some older female friends might help with this). Im not saying its definitely happening but if youre hanging out with younger guys they might not be interested in you because you are 34 and (dont all shout at me about how not all women want to get married, buy property and have babies) they could likely think you want to be all getting married, buying property and having babies.

I say this as someone who is your age, looks young, and has a younger boyfriend i met through younger friends. All my friends my age or very close to my age have/are planning to/talking about/just really want to get married, buy property and have babies and i'm with them on 1 or 2 out of 3 of those myself.

You sound pretty brave in being able to tell your guy friends you like them - would you be brave enough to ask them for a full-on critique or advice? They'll give you more of the opinion you need than a female friend. Afterall it was them you were interested in...
posted by moreteaplease at 9:07 AM on December 19, 2012

You *sound* like a swell catch and if you lived in my city I'd introduce you to some of my male friends in the same position.

I'm another one who's not a fan of online dating. Honestly, what worked for me was just finding a big group of people who shared an interest or two of mine and meeting with them regularly. Of course, this is easier said than done but side jobs, church, meet up groups are all possibilities. And even if you don't meet anybody at first there will always be new people coming in.
posted by Jess the Mess at 10:59 AM on December 19, 2012

we are all unlucky. It is rare to connect. However, in order to induce us to try and mate, we are installed with a bias towards seeing people succeed in romance so we will envy them and reproduce.

Keep trying. How? Smile, eye contact, compliment, light touching. Work on getting those down.
posted by Ironmouth at 11:14 AM on December 19, 2012

Developing feelings for friends is gross. It's unappealing that it took you more than a week or two to realize that I'm amazing, we might be compatible, and we should see where it goes. It feels like there's a degree of settling, just using the relationships available to you to fill a job opening. And the inability to bring up basic things like "I find you attractive" until there's a high level of trust and intimacy just screams of a difficulty to have open and honest conversations about the bigger stuff.

None of that is to say that you're a bad person. But I hope it explains why your current dating strategy is setting you up to fail. A closeted gay man is going to be your prime demographic. He won't feel initial sparks for you, he'll want to take it slow, he has a difficult time expressing his uncomfortable feelings, even though they're at the core of his being.

People want to be wanted. And that means that as shy as you are, and as scary as it is, you need to be express that openly. Online dating works so well because it allows us to avoid saying the obvious: "I want a relationship. I might want a relationship with you. I reserve the right to not want a relationship with you at any given moment". Otherwise, you're likely to meet a guy, and not think about romance until you know you *want* a relationship with him. At which point it's unlikely to be reciprocated, because if it was, he probably would have mentioned it by now.
posted by politikitty at 11:20 AM on December 19, 2012

Beyond a certain level of being attractive and having your shit together, I think it's mostly just luck and being open to possibilities. I'm 27 now and am marrying the third boyfriend I've ever had next year. I've confessed crushes to several people, had flings with half a dozen, but with the three I ended up spending years with, it all went very smoothly. I'm far from super-attractive -- I'm not hideous, but most guys I meet tend to not be interested in me. With these three, I could tell from the beginning that they were into me and I was into them -- it was just a matter of running into them. And that was luck -- one was in my high school class, one in my grad school program and the last one (my favorite one) I met at a special sort of trivia club. Sometimes I think about how my life would have panned out if I hadn't made the effort to go out on that rainy day to try out this new kind of trivia. Possibly, as Tim Minchin says, I'd have somebody else or maybe I would have gone another day and met him anyway? Or maybe I would be single right now and wondering why.
posted by peacheater at 1:12 PM on December 19, 2012 [1 favorite]

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