First Time Dating Blues.

March 20, 2011 9:13 PM

How do I overcome insecurity in the first stages of a possible (first) relationship?

First-time dater, here. I recently hit it off with a co-worker/friend, whom I've been "seeing" for the past couple of weeks. He's a little older than me -- I'm 23, he's 29 -- but I feel that we click, solidly, both personality-wise and sexually.

The problem is that I'm terribly insecure, and trying not to show it and/or drive him away. I've never "dated" anyone longer than 5 weeks (and I barely liked that guy -- it was a bad match from the beginning, but I was bored and craving romantic attention), never had any crushes reciprocated, etc. -- basically, all of my sexual experience comes from one- or two-night hookups that I started experimenting with in my last year of college, many of which ended in (my) heartbreak. I mean, I had my first real kiss at the tender age of 22.

I'm pretty good at hiding all of that information, as I've subscribed to the "fake it til' you make it" notion and had some success with it in the last year -- as in, I've become more outgoing, learned how to dress/do my hair/wear makeup, and have gotten a lot more male attention because of it -- to the point where people seem somewhat surprised when I tell them that I've never been in a relationship.

I feel that all this is why my co-worker was attracted to me in the first place, and now I'm afraid that this image is going to fall apart and he'll be repulsed by the neediness/insecurity I've managed to hide somewhat up until now.

I know that he's had three long-term girlfriends and lots more sexual experience than I have had. (I'm still an intercourse virgin because I wanted to wait until I was in a relationship, but I've decided not to reveal that until/if it gets to that point.) I think he likes me -- we've gone out a few times, he holds my hand, we crack each other up, and, maybe stupidly (on my part), we've moved pretty quickly to bedroom activities. But I'm starting to freak out royally. Example: he was busy all last week and I took that as a sign that he was totally over it and wanted nothing to do with me...and then I saw him this weekend, and everything was fine. I even cancelled my normal activities so that I could be "free" in case he called, which I know is ridiculous, but I couldn't help it, because I really wanted to see him. And I'm jealous of his extremely beautiful ex-girlfriend, and his hoardes of pretty, female friends that all live around this area and hang out with him frequently.

I suppose I'm so used to men not reciprocating my feelings and fading away rather than simply telling me they don't like me that I'm expecting the same thing to happen here, but I want to believe this has potential. At the same time, I don't want to freak him out by pressuring him to make it "official," even though I very much would like to be in a relationship with him. I guess it's hard not be anxious about it since I've never been in one or had sex, and am craving both very much.

That was long and rambly, so thanks for reading. Um, how do I fix this? I don't want to be anxious, or wondering what he's doing, or upset at myself for thinking that his gestures mean any more than they do. I really don't want to scare this guy away. (And don't worry, I haven't done anything crazy yet -- no confrontations or scary text messages -- just worried and beat myself up. A lot.)

Thanks MeFi -- you've never steered me wrong.

posted by themaskedwonder to human relations (14 answers total)

Being nervous about this stuff early in a relationship is totally normal, no matter your level of experience. I can't imagine why he would be less attracted to you because of this!

I find I feel the same way a lot when I actually care about the other person. You'll work through it, just do your best.
posted by clango at 10:09 PM on March 20, 2011

So weird...you sound exactly like me two years ago. I was in the same situation...never-been-in-a-relationship and dating a co-worker who was older and more experienced than myself (three long term girlfriends as well!). I was anxious and insecure about things, but we clicked, and he was patient with me through it all. Let it flow as best you can, and let his experience help ease you into your first relationship if it's meant to be. Everything you're feeling is what I've felt, so I assume it is "normal." Just take deep breaths and enjoy the experience. Focus on getting to know each other better first...the details of your relationship can be clarified later. Don't try too hard to conceal things about yourself from him, but uncover those details when the time feels right.
posted by evalunatik at 10:21 PM on March 20, 2011

First of all, you seem to have a surprisingly good, rational head on your shoulders, especially for a noob! Therefore, don't beat yourself up. That's step one. For your sake (especially yours) and his, be nice to yourself and take it easy—other people can smell insecurity and the "beat ups."

Look at it this way: You like him, but you don't know what's going to happen. And that's fine. Just live your life the way you would without him. Hang out with friends, do your work, go to meetings, play with your hobbies or classes, and if you all meet up in the middle? Great! That's how you take things slow.

Seriously—coming from a gal who's been in many relationships, don't cancel plans. Do the opposite of cancel plans. Maybe even make *more* plans, if you're afraid of "waiting by the phone for him." Honestly, waiting around was the biggest mistake from my 20s, and one easily made. Keep calm and carry on.

Healthy people, in my view, are attracted to people who have their own thing going.

Nobody's perfect, and nobody's "good" at this. I'm sure someone on here will come along with more insight, but those are my two cents. Good luck, my friend. :)
posted by functionequalsform at 10:22 PM on March 20, 2011 [8 favorites]

Yeah, you sound fine. If this does progress, usually there's a phase where you do want to spend all of your time with him, and unless one/both of the people are super busy, it usually happens. And then it'll get too much, and someone will want to back off, and the other person will freak out, etc., and then everything goes on. One example of a lot of things to expect. My point is that a lot of things happen in a relationship, especially at the beginning, and the important thing is that you can roll with the changes, enjoy yourself, and keep a little perspective.

Also, don't worry about exes that he still hangs out with. It's actually a good sign they're friends now. They're exes for a reason, and he's moved on and is ready for something new.

And of course, seconding that you shouldn't wait around for his calls or be super anxious to see him. There's no rush, and everything is so much better if you don't feel like you're sacrificing something for the chance of being together (I've made this mistake, it puts the relationship on a really bad path).
posted by devilsbrigade at 10:44 PM on March 20, 2011 [1 favorite]

the "fake it til' you make it" notion and had some success with it in the last year -- as in, I've become more outgoing, learned how to dress/do my hair/wear makeup

It sounds like you've got two personas going on -- the internal person that you really believe you are, and the person you're "faking it until you make it" as. It sounds like faking it is really working for you. That's awesome. Could you switch the way you think about it, so that that's no longer the "fake" part of you? Could you imagine you've already "made it?" Continue behaving as if you're already the person you want to be, and view this scared insecure side of yourself with the compassion it deserves, and the compassion that the "made it" person would surely offer to someone insecure?

However, I don't believe he'll be repulsed by the more insecure side of you. Some people find it endearing. Even if not, everyone has a side of themselves that's not their best side. (Think of your close friends. Great, but when they're really tired and cranky...?) So keep working to be the best person you can be, but don't worry that the existence of a weaker side is some fatal flaw. Just do whatever works to help you maintain your calm and confidence, be it yoga, spending time with friends, reading compliments from your high school yearbook, whatever.
posted by salvia at 11:49 PM on March 20, 2011 [5 favorites]

I feel that all this is why my co-worker was attracted to me in the first place, and now I'm afraid that this image is going to fall apart and he'll be repulsed by the neediness/insecurity I've managed to hide somewhat up until now.

Stop driving yourself nuts.
posted by rhizome at 12:58 AM on March 21, 2011

One of the best things about gaining some experience is that you learn to stop being insecure about wanting what *you* want. And you gain the perspective that no guy is the only one you'll ever feel this way about. And you become much much more secure about just walking away if something isn't working for *you,* rather than being freaked out about driving away the guy.

My personal opinion: this -- "I don't want to freak him out by pressuring him to make it "official," even though I very much would like to be in a relationship with him. is what often leads directly to this -- "men not reciprocating my feelings and fading away". You shouldn't be pressuring anyone, but in my opinion if someone freaks out at the mention that you want to date them exclusively, that's a pretty good sign that they don't know that they want the same. And I think it's much better to date people who *want* the same thing as you do. Don't buy into the idea that all guys are scared of relationships and you have to tiptoe around the idea and be NSA and casual, and one day if you're cool enough they'll just realize they want a relationship with you.

I just think if you're not ashamed of what *you* want, you won't end up flipping out and acting crazy. I think people do that when they keep submerging what they want and can't take it anymore. I think you can just tell him, "Hey, I really like you, and I don't really want to date anyone else. What do you think about that?"

If you don't want a relationship where the guy you're dating suddenly drops out of contact and is too busy to see you for a week on end, that's perfectly all right, no matter how legitimate his reasons are for that. It's okay to recognize the fact that some things bother you about a guy, and that doesn't necessarily make him a bad person, nor you a bad insecure unreasonable person, but just makes you not right for each other.
posted by Ashley801 at 5:19 AM on March 21, 2011 [5 favorites]

The only thing I would say is that I think a really critical benchmark of a good relationship made up of good people is the ability to ask for what you want and get it. If you can say "I need to be reassured you fancy me even though your ex girlfriend is really beautiful" it goes a long way to being the person you want to be in your relationships. Transparency beats mind-reading every time.
posted by DarlingBri at 6:22 AM on March 21, 2011 [5 favorites]

Good advice. The other thing that might be happening is sort of an emotional roller coaster that love/horny feelings create. Depending on your personality, these can manifest as personal insecurity, external insecurity, or both. It is important to realize these feelings are hormonal in nature, and to sort of box them in. You might start feeling that "he hasn't called in a while, I wonder what's going on, does he have another girlfriend, did he realize I'm a fraud, did he have a car accident" and have a freakout. Pull back a little bit and just realize this is just your brain's way of telling you that you miss him. Then pull back again and figure out what's an appropriate way to alleviate that.

And all relationships are built on some kind of trust. If someone likes you, you have to trust that it is genuine. Even if you are feeling insecure about yourself, that is kind of irrelevant to what *they* might be feeling. Maybe I don't believe myself to be attractive, but this other person seems to think that, who am I to judge what he thinks is attractive? Why should I give him excuses to not like me when I want him to like me?

Most people have insecurities of some kind or another. How we deal with them is what is important.

At the same time, try not to overdo it and exceed the envelope of the relationship. The relationship is a thing of its own, that both people create by interacting with each other. At any moment, there are limits to what it can take. "Let's be exclusive" on the first date is exceeding the envelope. "Let's date other people" after 10 years of marriage is almost always exceeding the envelope on the other end of the spectrum.
posted by gjc at 7:59 AM on March 21, 2011 [1 favorite]

functionequalsform: Do the opposite of cancel plans. Maybe even make *more* plans

Agreed! The purposes of intentionally being busy are:

-You don't have bags of time to freak out, become needy or obsess about what he's doing, stalk him online... or whatever you might be tempted to do!

-You will have lots of fun stories/jokes/experiences to relate, which will make you more attractive to him and to others.

-You will lower the stakes of the whole situation. If your social life doesn't hinge on one person, you will be able to handle rejection better - if it happens, I'm not saying it will.
posted by cranberrymonger at 10:20 AM on March 21, 2011

Let me help reassure you on his having lots of female friends and a pretty ex-girlfriend, which is actually a good sign.

Generally in my experience, guys with lots of good female friends are a more sensitive, understanding, sympathetic type who enjoy talking about interpersonal matters, not because they have ulterior motives and are waiting to get into bed with them. You also say this guy's been in 3 long-term relationships. Guys who have been in a few long-term relationships are looking for companionship and love. He's been around these female friends for a long time, in all probability he's dated or considered dating them already and came to the conclusion it wouldn't be a good match - he's not thinking of those girls in that way, but he does have an interest in you.

His ex-girlfriend and all these other girls are pretty, that should be a bit of a confidence boost. He wouldn't continue seeing you if you weren't attractive to him. Don't second-guess that.

Trust that he's interested in you and finds you attractive, and let the jealousy towards those girls go. It's understandable, but don't let it be unreasonable. Your best bet is to also make friends with these girls and gain their support. Jealousy could lead to making enemies and sinking your relationship before it even sails.

Things are going slowly between you two, which is fine - some guys need to develop the friendship part of the relationship before they allow themselves to get emotionally invested. If he feels you've clicked, he'll keep going. Just ask him if you're unsure, be direct, most guys appreciate that.
posted by lizbunny at 11:41 AM on March 21, 2011 [2 favorites]

Nthing "perfectly normal feelings".

Remember to be honest, and also to enjoy yourself. If it ends up not working out, don't blame yourself - for that case, it wasn't going to happen anyway. But, let's hope it's all good things from here on out.
posted by Citrus at 12:16 PM on March 21, 2011

Don't pretend to be a different person or hide your true self for a guy. The more you try to pretend, the more you'll wall yourself off from getting to know him for real. Also, don't cancel plans. Go on with your regular life and don't make him the #1 priority right off the bat. Been there, done that on both counts and it didn't work out well.
posted by elpea at 1:21 PM on March 21, 2011

I agree that one of the best defenses is staying busy. People have given a lot of good reasons above, but I'll also say that maintaining a full life of your own while dating someone allows you to make clearer decisions about whether you want a relationship with that person. It's good to take things slow -- not to avoid scaring him away, but so that you have time to check in with yourself. I've often mistaken a desire for being in a meaningful relationship for a desire to be with a particular person. I agree with Ashley801 that asking for what you want is important, but it may be too early to know for sure. Give it a few more weeks and remember that you're not just waiting for him to decide; you're also trying to find what's right for you.
posted by spinto at 6:24 AM on March 22, 2011