
I am on my freshman’s year in college and I met this awesome guy with whom I could have endless conversations and we were alike in so many ways I couldn’t help but sort of falling in love with him. For some reason he decided to quit college and go do something else, after only two months of us having first met. We still chat online very often and have long, deep conversations and right then I feel like I could tell him everything, about how I feel yet I’m afraid. I’m afraid because I have absolutely no idea how he feels about me.
I can say for sure that he lacks a good deal of self-esteem. He’s one of those guys in whom most girls see nothing of attractive (obviously because they fail to look inside). He’s confessed that he suffered real bad heartbreaks in the past and that has never had a girlfriend, to start with.
Now, me, not to sound full of myself (I’m actually not at all) but well, I am a photographic model and know from feedback that my looks are above average. And believe it or not, this is one of the reasons why I think he feels like there will never be a chance for the two of us. Because he thinks he’s worse than me, because he thinks I’m too good for him, that I’d never really notice a guy like him… and ironically, he’s indeed the one that I like! But you can tell his insecurity around girls. He sits at least five feet away from them, he doesn’t compliment them, he doesn’t even shake hands or kiss to say goodbye.
How could I let him know he is special without being too obvious or sounding desperate? Is it okay for a girl to make the first move and show him she’s interested?
Jessica
Dear Jessica,
I’ll cut right to the chase: guys who are painfully shy at first usually step up to the plate once they realize that you are interested! The myth how a woman shouldn’t make the first move is outdated and too passive for a modern woman to accept. Plus, guys that appear dorky or insecure on the surface often end up real sweethearts with a lot to offer! So if your love interest is too shy around girls, the ball is in your court, literally – so grow a pair and ask him out already!!! :-D
As for being physically more attractive than your partner. You may have noticed that supermodels rarely date supermodels. Being in the superficial industry, they know what it’s like to be the target of one-dimensional appreciation and know to look beyond mere appearance. It sounds like you are intuitively doing it already.
Think of your guy as a diamond in the rough. Once the debris of insecurity have been brushed away and his self-esteem polished by your TLC, you’ll have a sparkling young man on your arm!
Deerlings: have you ever made the first move? How did it work out?













go after him! he sounds like a real sweetheart
Renee H Reply:
October 24, 2009 at 10:02 pm
agreed! DO IT! In person is always best if you can!
My most fabulous relationship EVER started off with ME spending the cash and sending the first email on a dating website. The rest, is history.
For me, the person I want to have as a mate is someone who is above all things physical, also my best friend. I think you may have found that, so go after it!
If you like him thats all that matters. Even if he doesn’t return your feelings, what matters is that you tried. Its better to know than to wonder.
Go for it. You won’t regret it!
I agree, go for it! Guys like this are often some of the sweetest and most attentive partners you’ll ever find. They just need a little ego-boosting. :)
great advice there :)
Go for it, I say! I never believed in the waiting game, myself and have been the one to ask the guy out for many years. Even if they turn you down, it’s much better than never knowing!
i find it weird that this girl rather confides in you (a stranger) than in a friend. anyways, i think in general people miss out on lots of opportunity because they overthink things and find excuses not to confess their feelings. if its worth having then surely its worth fighting for and that also means taking a risk of getting hurt.
Yes I did, I made the first move :) Albeit through MSN! We’ve been dating for 2 years now. I wish I still had the balls I had in the beginning though! Now I’ve become a bit ‘softer’ – does anyone have that problem? Or am I just crazy?
I made the first move! ^^ I was really surprised at myself… I usually wait maybe six months before intentionally letting on anything, but I asked out my first/current/beloved boyfriend only a week after we met! Go with your gut – if he seems like a kind, sweet, loving person, go for it. :D
Kathrina Reply:
October 22, 2009 at 3:04 pm
My current bf [and future husband] did the 1st move yet he was terribly shy so i understand how Jessica feels since she’s “better looking” than his crush but Doe is right when they know ure interested somehow they move their shyness away and ask u out but if u dont wanna wait GO FOR IT it seems like there’s a connection there :D
good luck.
I agree take a leap of faith and see what happens. Ive been in this situation before a few times and more often than not it works out.
I made the first move and now I’m planning to marry the guy!
I’d got sick of waiting forever and being too scared to do anything, I’d missed the window with others. So I decided to bite the bullet and kissed him after a perfect evening together.
He is conventionally less attractive than me, but to me he’s beautiful, we’re perfectly matched <3
I made the first move with my guy (while I already had a boyfriend, shame on me…) by walking up and talking to him. I ended up leaving my boyfriend for him! We’ve been happily together for two years now :) I know he’s the one and we plan to get married in a few years!
Go for it! I did it, and ended up with my wonderful boyfriend who supports me in everything I do! The thing is, he was so afraid of me he wouldn’t even invite me to his birthday, and when he did, he kept trying to have one person between us, because he felt he wasn’t good enough for me. So I plopped myself down next to him hugged him and gave him a Happy Birthday Kiss on the cheek and he never looked back.
The thing is, let him know how you feel!
it’s totally okay to make the first move! i made the first move on my bf/i even kissed him first (not the other way around) and we’ve been together for almost 2yrs!
I made all the moves with one guy, and ended up with him on & off for 10 years. It didn’t end that great, but I learn’t a lot about myself, and guys (compromise, but don’t let them walk over you), and I have a policy of no regrets because life is short. Just scope things out, and if he doesn’t seem keen after your first enquiry, then leave well alone, if it’s mean’t to be, he’ll come back to you. Sometimes they need a bit of time to think about it. And unfortunately it’s true, there are many more fish in the sea.
In my experience, a guy is usually pretty impressed when the girl makes the first move! Also, you really don’t want to let the opportunity to catch a ‘diamond in the rough’ pass you by. You’ll probably find that if you bring him out of his shell, he’ll be very thankful for it and that will make your relationship stronger. Go for it! :]
Good advice. Life is short, let ‘em know you care.
What a timely article. Just today I texted my friend to drivel on about how the very same thing (except, shame on me, I’ve now known him for over a year!).
Now then, time to grow some balls…
Kiri Reply:
October 21, 2009 at 3:17 pm
I wish you the best of luck, and I really do hope it turns out well for you.
I’m trying to find the guts to tell a guy I know just how I feel, but of course, it being me, the whole situation has to be more complicated.
Megan J. Reply:
October 22, 2009 at 3:35 am
Rather than balls, I like to say “Ovarian Fortitude”. :D
Seriously, balls are such a sensitive and vulnerable set of things…*chuckles*
Good luck!:)
Libby Reply:
October 22, 2009 at 12:00 pm
Aww, thank you both! I’ll see him in a lecture next Tuesday, so hopefully I’ll have worked up the courage by then! :D
And good luck to you too, Kiri! :)
Definitely go for him! :) No use waiting around if you know you like someone!
I made the first move with my boyfriend of a year. I asked him to hang out a few times after seeing that we had so much in common and then I just went for it and kissed him! he got the hint and asked if i wanted to date him. :P
I am so happy that I did make the first move because our relationship is just so fulfilling!
I had been in a similar situation; I met such a great guy, but he seemed a bit shy in front of my “culture” (I’m a real nerd) and the fact I’m an artistic nude model… So lately, yes, I decided to grow some balls and kissed him. He wasn’t so shy after that ;) We’re now happy in love; let’s hope it lasts!
i was in this exact situation (it was even my freshman year at college!)
i took the first move and we’ve been dating now for three years!
you will never be as sorry as you are when you realize you missed an opportunity. go for it.
I say go for it. When I was in highschool I fell in love with my best friends ex (I should probably mention it they ended it on good terms). He was quite and insecure and didn’t want anything to do with girls but be their friend. I had mentioned to him many times that he should ask someone out but he never would. It came to the point where I was giving up and my best friend (the one that had dated him before) told him he needed to go out with me and he finally accepted my offer of a date. Needless to say we have dated for 5 years now, we are engaged and after all the insecurity has been wiped away he is the most amazing man i have ever met. Take Doe’s advice, it worked for me.
judging from your letter you really like him, so I’d say go for it (like everyon else here ;) I’m pretty shy when it comes to the guys I like, so I’m usually too chicken to say anything, but I wish I could.
most people regret the things they didn’t do, not the things they did.
good luck! ^^
Good answer Doe. If some girl doesn’t make the 1st move witha guy like that he’ll never get a girlfriend.
No I’ve never made the 1st move. My pale skin (a pinker 1 shade lighter than your’s Doe) made me basically a leper in school. only two boys liked me that I liked back all through highschool. They were both white with blue eyes which isn’t even my type but it was “slim pickins”. The 1st turned out to be a loser so I’m glad I was too nervous. The second was on a sort of “break” with his girlfriend and he was too upset then they got back together on and off until he graduated. I just don’t think it would have been appropriate. I also liked this hot Russian guy in my summer art class at 1st he seemed interested but as he got to know my friends DD’s better my C’s started to look more like just friends. He should have taken me since my friend wasn’t interested and neither Sergei or I got dates that summer. =/
I’ve given up now. I’m turning 20 soon, I’ve been obese for the past 2.5 yrs and I feel like I’m too old for 1st dates. I’ll never have a guy want to hold my hand before I F*** him.
Kat A Reply:
October 21, 2009 at 4:41 pm
Don’t give up!! I’ve totally been there. I know it hurts to feel like no one’s into you, and sometimes it seems like guys are only interested in sex. You are NEVER too old for a first date!! I’m your age, and this semester I decided to take matters into my own hands as far as boys go. I’ve already had two first dates (they were both dorks, but now I know, right?) and I’ve already set my sights on another cutie! It IS possible to find nice guys who aren’t shallow, no matter who you are or how much you weigh. Many guys love chicks with curves, and judging by your facebook pic, you are by no means unattractive. I’ve just figured out after 19 years that snagging nice guys takes a lot of patience and determination, as well as confidence and friendliness. The best way to meet people is to be outgoing and cheerful. Just don’t give up!!
Mar Reply:
October 21, 2009 at 5:07 pm
Hey, don’t say never. I agree with Kat that you are definitely attractive. Finding the right guy for you is always a bit of an undertaking, but never give up hope. I’m 19 too and I’m certainly not too old for first dates! I know lots of people older than us who still go out on those. :) You don’t need to have your future husband, your dream house, and your career all planned out right this second. Give it time! Meet guys. I bet you there are a few out there who are in love with you right now but are too chicken to show it. (Trust me. There always are.)
It sucks to be single but there are always people out there for you — you just have to find them. Say hi to people you meet. Put on your fave outfit and go to a friend’s party. Let yourself feel sexy, & then act like it. Trust me, there is a guy out there just as sad and lonely as you, waiting for you to walk into his life and fill that gap. So don’t ever give up!
Suzanne C. Reply:
October 21, 2009 at 6:03 pm
That pic is 3 years old thats why I was pretty; I was 16. I’m not sad and lonely, maybe a little bitter but mostly apathetic. When I said I’d given up I wasn’t whining I meant it.
I guess I shouldn’t have shared i just wanted to explain why i’d never made the 1st move. Thanks for the photo compliments anyway.
Mar Reply:
October 21, 2009 at 8:04 pm
I’m sorry if I came across as condescending. Your love life is your choice, of course. You just sounded so discouraged about it that I wanted to offer support. Sorry for the misunderstanding. The best of luck to you in all your dreams & endeavors, my friend. :)
Agnes Reply:
October 21, 2009 at 8:50 pm
Read my example below!! I am just like you are, and I always was like you are, but dont give up! I always thought the same things you are thinking about yourself right now. And it was wort waiting!!! Now I have the man of my dreams, my first real boyfriend, but the only one who ever was appropriate for me. and I’m now 22, so dont worry! Your time will come!!
Suzanne C. Reply:
October 21, 2009 at 11:42 pm
Thanks being so supportive everyone. I’m not giving up for eternity necesarilly but well thats not the point. I was just trying to answer the question. I’ve needed to figure out how to be more clear for a long time! Sorry for any confusion.
Good advice, she needs to go for it! Nothing ventured, nothing gained!
:3 I made the first move once. I approached my high school crush out on the front lawn of our school. 6 years later, we’re moving in together, and we’re getting our very own little puppy! Hurray!
Hmm… technically my boyfriend asked me out first, but I had to break up with someone before accepting, so I said no.
2 weeks later I asked him out over the counter in his place of work.
4 days later I kissed him first.
3 years on, I’m sitting on my hands trying not to propose first, but I gotta let him have SOMETHIN’ on me! (^_^)
Great advice.
I would say that I made the first move. I asked him if I could stay the night! lol Technically, it was for convenience’s sake because a group of us were going out of town early the next morning (at least, that was my excuse). But me staying over at his place changed everything. I also brought up the “us” talk. Monday was our three year anniversary. :D
We asked each other out. I proposed to him, though. :)
Hmm…I have mixed feelings. I’m kinda concerned about his lack of self-esteem. Maybe I’m reading too much into it, but I just don’t want Jessica thinking she has to fix him and be that cure that makes him feel good about himself…anytime you think you can try to fix a guy, it doesn’t work. My fiance is kinda dorky, and not that he’s unattractive, but he’s not what most girls would seek after. I have a hard time believing it, but since I’m anonymous, I’ll just say it…people tell me all the time that I’m beautiful and have all my life, so I’ll go out on a limb and say I am not the kind of girl people would expect to be with a guy like him. But I think he’s so cute, and he lights up my world…I can’t imagine anyone being a better fit for me and me for him…we really complement each other, and what we have in common are the important things that truly matter. When he first wanted to ask me out, he got so nervous (he has admitted it was largely due to my looks) that he backed out…but then he just gritted his teeth and did it after I SLIGHTLY hinted around that I was interested. I gave him just enough to get the idea that he should try, without actually letting him know. I wasn’t trying to play games; I just wanted him to be the one to do it. Maybe it’s just me, but I wanted a guy who at least had enough confidence to ask me out. I’m not saying she shouldn’t ask him out…every situation is different, and I think it’s perfectly fine for girls to make the first move…but I do wonder about his self-esteem issue, and I wonder if maybe she should just give him a little hint and then let him follow through? I just think when a guy is REALLY interested in a girl, he’ll find a way to work up the nerve to pursue it no matter what. He would NOT be spending all that time on her if he weren’t interested. Maybe she can just say something a little flirty and see how he responds…he will get the message that the path is clear and then make his move! Making the first move and being accepted…now THAT should help his confidence level. :)
I made the first move when I realised that a guy was too shy and too thick to realise that I was flirting. I literally just said something along the lines of “so when are you going to ask me out?” It made him feel like he was in control and wasn’t worried about hurting my feelings because he easily could have said “I’d rather just be friends”
Turns out he was into me. 4 years later we’re married and have a baby!!!
I say go for it, make the first move, and if he really does have self esteem issues you might have to be pretty obvious about it, like I was.
Catherine Reply:
October 22, 2009 at 7:13 am
Mine was the same! Way too shy to ask me out though we were already close friends; After one successful “first date”, nearly five years later we’re planning to spend the rest of our lives together in wedded bliss…
He was a bit dorky-looking and nervous, now he’s blossomed into a gorgeous guy, much more relaxed about everything.
I say go for it! Especially in a way which makes him feel empowered.
Even if he doesn’t return your feelings, if you really love him it would be best to tell him, primarily because that ought to be a ginormous self-esteem boost for him and a dramatic change for his own future, with or without you (sorry if that sounds really pessimistic, that’s not how i’m trying to sound). Definitely tell him– there’s a 50% chance at least that it will merit improvement in your life and a 100% chance that it will improve his outlook on life.
Jessica,
This sounds just like my ex, and I can promise you, my biggest regret is that I ever mistreated him. He’s the sweetest guy you could ever meet.
After I broke up with him, I found his blog and, being too nosy for my own good, I went back and read the entries from when we got together. He wrote about how he’d never imagined he’d have a chance with me because, in his eyes, I was too attractive for him and whenever we went out together (as friends) I was always receiving attention from other people, etc. but the fact was that I wanted to be with him (at the time), not those other people, and I think I boosted his confidence just because of that.
…unfortunately, I had to go and undo it all, which had the opposite effect on his self-esteem. Actually, I just don’t want a relationship, but obviously I still hurt my ex when I broke up with him. So, if I was going to give any warning, it would be this: if you get together with this guy and he turns out to be as lovely as he sounds, take care of him and always remember that what’s inside is much more important in the long run. And if it happens that he doesn’t return your feelings, he will probably still be grateful and flattered.
And the bottom line is, as other people have said, never never never hold back through fear of rejection! You’ll never know if you don’t try!
Good luck :)
x
u’ve made the first move :D i always do, theres no shame in it. most of the guys ahve turned out to be dicks, but oh well, you live and learn ;)
I would ask him out, I am in the same boat as the reader in most cases, only the guy I have my heart set on is in a relationship and therefor I can’t do much about it. I think she should go for him while she can, she will regret it if she holds back.
I made the first move once and it worked out splendidly! Of course I felt like I was going to puke while I was doing it, but I imagine that’s how anyone feels before they ask someone else out, guy or girl. My gent said yes, and later admitted that he was nervous about asking me, so he was really glad I did! Go for it if you like him!
Funny this entry should pop up! I’m pretty much in the same boat, but I feel the same way in that no one would go out with ME either(I’m kinda weird and scared around boys). I’m a chicken in EVERYTHING, though! I can’t do something new without REALLY regretting it later, thinking of how stupid I looked. AND my mother wouldn’t like me dating too much, she’s pretty sure he’s gay!XD I’m thinking of a good way to do it, sneaky if i have to, a few days before fall formal…
Actually I did the first step when I got to know my boyfriend.
I’ve always been a girl that wasn’t too popular to boys, I always had too much weight and was always a bit different. That’s why I never had the courage to speak to a boy that I thought was cute. And I never had a boyfriend before I was 21. I simply never met anyone that fell in love with me and that I could fall in love with (or the opposite of course).
But then I met him. It was like heaven after a long time that I almost finished the topic love for me. He was everything I ever dreamed of, but unfortunately I knew he was married to another woman. I almost died knowing that he never would be with me.
That’s why we decided, better not to see us again. And some time went by and I didn’t hear from him. But then I realised that I couldn’t let him go, he was just too precious for me and my life.
So I found out his mobile number by asking out the secretary in the company he works in. She was really pleased to help me (she said actually she must not give away the private numbers, but for this cute case she will help me).
I called him and we immediately started talking as if nothing would have happened.
Well the problem of him bein married was still there and I refused to kiss him or something like that when he was still with her. It felt just so wrong.
And then the most incredible thing happened and I still believe, that this was something like a divine stroke of fate or so, because just at that time it happened that his wife told him, she’s about to leave him because she had another boyfriend since quite some time. It was so ridiculously fitting my problem, because this was the only way that this problem could have been solved and I mean what chances were there for this case to happen?
So and that’s our story, we are together now for about 9 months and I still love him like on the first day we met. He’s the best thing that ever happened to me and I am really glad that I acted against all rules and called him at this one evening. It was my way to happiness.
I basically bullied my boyfriend to date me. So glad I did it!
i made the first move twice, and i was rejected, and i took it ok, months or even a couple years later they were asking ME out and i was the one saying no xD
i made the first move by asking this boy out to the movies, and kissing him that same day. now, two years later, we are happily dating and living together! i couldn’t be happier! :)
Good luck Jessica!
I myself have made the first move, and it ended up….. well, disastrously! I liked him very much, but the feeling wasn’t mutual. I’m no great looker but I refuse to let that sort of rejection get me down. For now I choose to be happy with my own company until the time comes to meet someone who does want to be with me.
I’m sorry, but it sounds like this guy is playing on your sensitivity. If he is not much to look at and he’s whining to a beautiful girl about it, he’s sounds a lot more confident than he’s made himself out to be. I’m all for girls making the first move on a guy she’s interested in, but it sounds like there’s something else going on with him. I would dig for a little dirt before you try to get too close, for instance, why did he have to drop out of school after 2 months (did he get his girlfriend pregnant and have to get a full time job)? Why do you only chat on line? Maybe he is physically distant because he is unavailable? You are young and beautiful, you have a lot to look forward to in life and love, take your time in getting to know someone and in giving away your heart. Good luck girl <3
Me Reply:
October 22, 2009 at 5:33 pm
I hadn’t thought along those lines…good point. Maybe he is just fine…but these are some good questions she should raise!
Well, I’m all for making the first move, since everytime I’ve done it it’s turned out pretty well. My current boyfriend was the guy I confided in about my past 3 relationships, and who has always been there for me. I finally asked him how he felt when I was single, we went to my senior prom together, and we’ve been together for over 2 years. Life is good.
If you feel like it’s the right thing to do, I definitely recommend talking to him about it. Good luck!
Jessica, go for it!! Sounds like you’ve got a good guy there and I’m sure you know how hard those are to find these days. :)
In regards to Doe’s question…
I’ve actually made the first move four times in my present relationship.
The first was when we had been going out for a little while and I finally made some comment to the effect of, “So, are we girlfriend/boyfriend or what?”, 2nd: I initiated our first kiss, 3rd: I said “I Love you.” first, and the fourth….well, that’s private.;D
-In each instance, had I been a little more patient he would have gotten around to each of these things on his own, first. But, I’m impatient…wish I’d waited though.;)
This guy was my 3rd boyfriend, the first two lasting only 6mos. between the two, and already we’ve been going strong for just over 9yrs. now with marriage and children on the horizon.
-we call eachother “domestic partners” since we’ve been living together for over 7yrs. but aren’t yet married.*chuckles*
And Jessica, my guy was/is quiet, too and can be shy around women. I honestly think that these guys are the best, they are incredibly thoughtful and sensitive to your wants/needs…most of the time.
-If he’s a Geek, all the better!:D
Best of luck!:)
I think it’s fine to make the first move, I did and it’s working out ok so far ;) I went for the same approach as Daisy above and said something along the lines of ‘so how much more obvious do I have to be before you ask me out?!’
But I agree with some previous commenters, you can’t fix his issues and if once he realises you’re interested he comes out of his shell that’s great, but if he’s perpetually looking to you to boost his self esteem that’s not a good situation to be in, and worse you may find yourself later unable to get out of it without making his problems worse.
When I was 15, I asked somebody out for the first time. Even though he turned me down, I still don’t regret it. Since then, almost all of my best relationships have been because I had the guts to ask a guy out, even if I didn’t think he was interested. Even my current (wonderful, stupendous, amazingtastic) boyfriend is one that I asked out rather than the other way around. Go for it. No matter what his answer, asking him will be an empowering experience if you’ve never done it before.
I absolutely made the first move and now I have the most wonderful man in my life. I am truly blessed. I can talk to him better than any other person. His hugs are the most comforting. He makes me laugh and doesnt mind my dorky interior because it makes him laugh.
I ALMOST always make the first move :D
It usually ends up with me getting what I want, but because I’m pretty bad at ‘taking things slow’ and ‘getting to know eachother’, I often end up realizing he wasn’t the person I thought he was at all!
So, now that I’m older, and know these things, I’ll just say: Be sure it’s HIM you want, and not just some part of his personality that you wish you yourself had.
Good luck Jessica
In response to Doe’s question:
After an entire lifetime of -knowing- that I was a lesbian, I fell for a boy the second semester of my first year of college. I didn’t know what to do, but I knew that I never wanted to have to live with regrets or wondering “what if”.
So, even though I had come out to him and all of my friends as soon as I met them, I told him that I liked him. Guess what? It was mutual.
We’ve been together for half a year now with no intention or sign of slowing down. I’m so glad that I made the first move; I never believed in true love or soulmates until I met this boy. :)
I can say I was in the exact same situation, only me and my man are both painfully shy and he ended up making the first move, at the same moment I wanted to. Lawl. Before I could open my mouth to say “I like you and I think we should date.” He grabbed me, kissed me, then said the exact same thing. I was kinda dumbfounded but it all worked out in the end. ^_^
Normally I like to be pursued (what girl doesn’t?) but every once in a while it is totally worth it to make the first move!
When I got tired of planning parties and inviting the boy I like, along with mutual friends so he wouldn’t be uncomfortable, and waiting for him to make the first move (he is very shy, so…no), I lured him to my side with a hard-to-get ticket to a J-rock show.
It’s been almost 2 years and we both think it’s one of the luckiest moves I have ever made.