Should I date someone out of my league?

[mr_dave]

This is going to sound weird but here goes....

 

I've dabbled in OLD for a couple of weeks now, messaging girls on OK Cupid, and finally one has bitten, and has replied to my messages with interest, asking me as many questions as I have her.

 

So I asked her if she wanted to meet up this saturday for a drink, she said yes and seems really keen. She added me on facebook and she is really as beautiful as her OLD profile pictures, with a much better, more lucrative job than I have, plus she has a car, her own place.... The latter things don't really faze me too much because I'm working towards them achieving myself.

 

So I looked at a few of her photos (as you do) and I saw a few pictures of her with her ex. He was a well known guy in the years above me at school, he has model looks, and (don't laugh) I know him to be really well endowed - all the girls were after him at school, he was on the football team, and word gets around about those kind of things. He was particularly gifted in that department. And I'm not - being just about average size.

 

Now I know people say size doesn't matter etc., but as I only have sex in relationships.. well if it gets that far I imagine she'd likely be disappointed.

Having been cheated on previously, I really don't want to be in a situation where I'm not quite up to the mark sexually - at worst being cheated on again, at best her being with me in spite of it, but wishing I were better equipped. Which is a position I'd hate to be in.

There are endless threads about this kind of cuckoldry stuff all over the internet, and what some women in this position do, which really makes me wary.

 

I know the stupidest question you can ask is how well endowed a girl's ex was, but if you know the information beforehand....

 

Any thoughts?

 

TL;DR

Set up date with stunning girl out of my league.

Since found out for certain that her ex was better looking, better endowed.

Should I still go on the date?

[Sivok]

BREAKING NEWS - Looks aren't everything. There's a reason he's her ex. She's enjoying your company and is attracted enough to you to warrant a date. Don't blow it before you even meet up with her man.

[Targetlock]

there is no such thing as a 'league' (how would you work out what your league is anyway?) and i really don't like the talk about it, its just negativity and gets people down, all that matters is whether you like them and whether they like you, if you like her message her! you never know what might happen

[pickflicker]

They aren't out of your league if they want to date you. Just go out.

[Ruby Slippers]

My last boyfriend had model looks, made a lot of money, and was well-endowed. He was also vain, arrogant, more controlling and mean as time went on, and overall a selfish lover. He wanted to get married, but I couldn't do it without real love and the mutual desire to please and adore. I left him.

 

I want someone who's attractive to me, but not so good-looking and swarmed with female attention that he doesn't appreciate me and treat me well. Most women would agree with me.

 

Don't disqualify yourself. You may be exactly what she's looking for. Good luck!

[mr_dave]

Thanks for your advice guys.

[BeholdtheMan]

TL;DR

Set up date with stunning girl out of my league.

Since found out for certain that her ex was better looking, better endowed.

Should I still go on the date?

 

Let go of your insecurities. Women don't like insecure men. I don't like insecure men...and I'm a man.

 

Where's your confidence man? Look at you going on about how big her ex-boyfriend's willy is. Who cares?! She's interested in you. Have pride and dignity in who you are. If she ends up not liking who you are, well...there are plenty of fish in the sea aren't there?

[carhill]

If you are dating someone, they're not out of your league

 

Yes, go on the date. People are people. Either there's mutual interest or there is not. Let go of expectations and analysis. Just live.

[Ruby Slippers]

This poster is right. If you bring your insecurities to dating this woman, you aren't going to be yourself and will sabotage yourself. Insecurity makes people jealous, controlling and mean. You need to work on that about yourself...where did all this self loathing come from, dude?

Whatever happened to pushing yourself out of your comfort zone and trying something new and challenging? It's just a date.

 

I almost didn't date my last boyfriend because I thought he was too good-looking and widely attractive to women for me. Yes, he turned out to be vain, arrogant, and unappreciative, as I feared from the start that he might be. But in other ways he was loving, encouraging, and helped me grow as a person. I became much more confident and fearless while we were together, and that didn't change when I left him. The mystique of the super-hot guy was unraveled, and I realized he's just another man, with flaws and weaknesses like us all.

 

Now I'm not afraid to date anybody, don't think any man is too good for me.

 

This will be a great learning experience, even if it doesn't get past the first date.

[Ruby Slippers]

Lord knows I've had my share of dating guys who thought *I* was out of their league. Never again.

I've been in that situation, getting comments like, "You're too good for me", "you could get someone hotter", and so on. But those experiences were valuable and educational, too. It showed me how silly and self-defeating we can be with our insecurities.

[Andy_K]

Send her a picture of your penis. That way, you won't even have to worry about going on a first date.

 

And if by some miracle she still wants to see you, she'll know what she is letting herself in for!

[LEEVIT2F8]

There are a few options for you.

 

1. Just go out with this girl and see where it leads. Have a couple of drinks and have some fun.

 

2. Put off the date. Get your own place, car, and a better job. Then grow a bigger penis and learn how to use it. Then ask her out again.

 

Personally, I'd go with option one.

[Ninjainpajamas]

"Should I date someone out of my league?"

 

Yes you should, so you can realize that this is just another human being...not some perfect droid from another planet.

 

Comparing yourself to her ex's is an insecure thing to do, you as a man have to be a bit more confident in yourself, even if you're a bit in doubt...it's "normal" for women to feel this way but for men you've got to retain your self-esteem or it just makes you look jealous or weak, which is generally acceptable for women to feel and express, but not for men.

 

You also need to be aware that a lot of these guys, because of their options...tend to be very arrogant and entitled, they care a lot less about things that the average guy would worry or care about because for them these are things they'd never have to think about...women stick around just because they look up to them, they basically put them on a pedestal like "nice guys" do with women and then they put with all kinds of crap because they know other women want him and he's got options to move on, and the competitive spirit of women would not allow that, especially after naturally developing feelings, and if he you're good in bed on top of it and word gets around...you might actually feel a bit like a god in your own little bubble.

 

But at any rate, this should all be irrelevant to you...she's single and available, whether she's just a bit over the "hot guy" and just looking for a "good guy" might be your string of luck, this might give you an opportunity to be who you are and bring qualities to a dating/relationship that this other more desirable man doesn't have to really bother himself with...you'll try harder, you'll be more keen on being accepted and validated and she'll enjoy the attention and effort.

 

What happens out of this at times however is either a guy feels too insecure and self-conscious because of his own self-esteem and self-doubt and causes rifts in the situation that causes him to sabotage the situation itself, or he tries to play it too cool and confident and ends up shooting himself in the foot...so just be yourself, and hopefully if things do work out you don't become a jerk yourself and overly confident because you once dated the "hot chick" so now you think everyone in your league is somebody you're too good for now.

[mr_dave]

Thanks again everyone

 

I know, it's down to my lack of confidence I guess.

Being dumped by someone I was a "perfect boyfriend" to (according to her mum, sister, friends) led me to question everything about myself.

My self esteem took a nosedive.

 

I will go on the date, I have made my mind up, and try to enjoy it.

I'm incredibly nervous already!

 

I'm not the kind of guy to bring someone else down, on the contrary, I would always tell my ex-girlfriend how much I loved her, made her feel good about herself and wanted her to make the best of herself, encouraging her to continue studying, go away to university etc.

 

Thanks for all your input.

[Ruby Slippers]

I've done my time trying to reassure guys who say that to me.

Me, too. And now I recognize that if a guy says something self-defeating like that, he's pretty much already defeated himself in his mind, and it's not going to work.

 

But I maintain that those experiences were valuable, for me and for them. Listening to someone else express self-doubt about things that I hadn't even considered made me realize the folly of projecting your insecurities onto others.

 

For example, when I've gotten the "you could get a hotter guy" comments, my first thought was that the guy who's saying that is plenty attractive to me, and I was never looking for someone hotter. I don't date anybody just to fill time. If I wasn't interested and attracted, I wouldn't bother.

 

I think what mr_dave can learn from this is not to disqualify himself before he's even started the race. Don't stop running to tell the other competitors or the referee that you might not be fast enough, strong enough, have enough endurance, that the guy who ran the race last year had longer legs, a better record. Just run the race, give it all you've got, and enjoy the experience. You might surprise yourself.

 

Whatever happens with this woman, he's going to learn something valuable from the experience.

Edited February 27, 2014 by Ruby Slippers

[mr_dave]

Update.....

 

So we actually met up tonight, she forgot she had a friend's birthday this weekend.

 

Wow, she is without any exaggeration the most gorgeous girl I have ever laid my eyes upon, right down to her nose.

 

She was a little flustered though as she had had a long, stressful day at work, seemed a little tired, and couldn't drink more than half a beer because she was driving.

We talked for a couple of hours and it flowed nicely, but as we weren't quite sat facing each other it was a little hard to connect and look into her eyes etc. So when she left (she said she had a lesson to plan for the morning, she's a teacher) it wouldn't have felt right to give her a kiss, touch her arm etc. And she didn't really wait around and give me chance.

She did say during the conversation that she would teach me how to drink properly, go with me to this nice restaurant I hadn't been to yet etc.

 

I'm going to send her a message to say I enjoyed it, ask for another date etc.

Is the day after too soon?

Edited February 27, 2014 by mr_dave

[carhill]

Tip: When hearing such things, friendly banter dictates making a solid plan if possible at that moment. Just flow right into it. With that water now under the bridge, call her when you feel like it. Don't worry about rules. Do what you want. If it works out, it does.

[mr_dave]

Thanks carhill.

 

I'll give it a day and then send her a message, if she doesn't want to then its easier for her to be honest, rather than me calling her and her agreeing out of politeness.

 

I'm glad I went now. I was a really nervous and did jumble up my words a touch.

I'm really shy and I've never even been able to smile at beautiful girls without looking away, but I guess now if I can talk to her I can talk to anyone.

 

But wow!

[Targetlock]

well done, glad to see you went for it as the conversation seemed to naturally flow in to mentioning what to do for the next date, go ahead call her! ask her how that lesson she had planned went.

[Imajerk17]

The day after is fine. It wouldn't hurt to call her either. I'm seeing that in dating, showing interest and keeping the momentum going is what you want to be doing. In fact it's the new playing-it-cool.

Edited February 28, 2014 by Imajerk17

[mr_dave]

Yeah I'll contact her tomorrow night I think. If she would like to meet again, then it doesn't really matter when I ask her I guess..

[Ruby Slippers]

I'll give it a day and then send her a message, if she doesn't want to then its easier for her to be honest, rather than me calling her and her agreeing out of politeness.

 

I'm glad I went now. I was a really nervous and did jumble up my words a touch.

I'm really shy and I've never even been able to smile at beautiful girls without looking away, but I guess now if I can talk to her I can talk to anyone.

 

But wow!

I think this is the perfect opportunity for you to develop your confidence. If you want to call her, CALL HER. A guy who calls me makes a much better impression than one who texts. I'm in my 30s, and I know the 20-somethings conduct most social interactions via text now. But I'm dating again, and the guys who text me to ask me out completely kill my desire. The ones who call excite me. It doesn't mean he's THE GUY because he calls, but he's DEFINITELY not the guy if he texts to ask me out. Total girl boner killer.

 

If you want her, GO GET HER

[Leigh 87]

I've done my time trying to reassure guys who say that to me. What I find soon enough is that they go way out of their way to find something negative they can hang their hat on... most of the time about stuff that isn't even true. It's just some junk they made up in their mind to feel better about themselves.

 

 

I recently dated a guy who wasn't the best looking guy I've ever dated... wasn't the most accomplished I've ever dated... but that's not what I'm looking for. I'm looking for a guy I can trust and who I have things in common with, who wants to build a relationship. He would not give up this idea that I am SOO accomplished, and why would I want to be with him?? I'm SOOO athletic, and why would I want to be with him??

 

 

I thought, ok, if that's how you feel, then join me at the gym. If that's how you feel, then sign up for some classes, join a volunteer group....SOMETHING... don't make ME feel like a freak just because he hasn't done what I've done or whatever.

 

 

Sure enough... I was at a party the other day with him. In a conversation with a guy we were just getting to know, he says "we are just friends. She just keeps me around until she finds some doctor or lawyer"...

 

 

Which couldn't be further from the truth. My fiancée who died never went to college... and he knows that.

 

 

So now, I don't feel like going to events like that with him. If he's going to use his insecurities to trash me to people. It's BS.

 

 

 

 

I am really sorry about your Fiance:(

 

That was pretty un called for, the remarks your date made in front of people; how embarrassing:o

 

My boyfriend hasn't been to college but he is perfectly intelligent. I am finishing a college degree plus a diploma or two along the way.

 

He is slim and fit where as I am "curvy" and admittedly a little soft and could stand to lose 10 lbs.

 

I don't stress about it; I just started going to the gym instead.

 

Why feel bad about things when you can easily do easy things to better your own situation?

[mr_dave]

I think this is the perfect opportunity for you to develop your confidence. If you want to call her, CALL HER. A guy who calls me makes a much better impression than one who texts. I'm in my 30s, and I know the 20-somethings conduct most social interactions via text now. But I'm dating again, and the guys who text me to ask me out completely kill my desire. The ones who call excite me. It doesn't mean he's THE GUY because he calls, but he's DEFINITELY not the guy if he texts to ask me out. Total girl boner killer.

 

If you want her, GO GET HER

 

Thanks for your advice Ruby Slippers!

Unfortunately I possess a rather dour voice, so I think I'll send a message this time. Kind of like Kimi Raikkonen meets Andy Murray.. (I think only an sports fan would get that, but hey..)

Don't want to put her off!

[mr_dave]

Update...

 

I messaged her the day after date one saying I had really enjoyed myself and suggested taking her out to get some tapas. (her favourite food)

She said that sounded great, so I suggested this coming saturday, to which she agreed. So it seems I have a second date.

 

I figured our next date should be at the weekend so she isn't tired/flustered after work, or constrained in how long she can stay out.

 

Its six days away though.. I have a couple more questions..

 

Should I message her much before then? On the Wednesday she told me she is playing a netball match, I could perhaps ask her how it went?

 

Also, if it's going well, how can I escalate it just a bit to let her know I'm very interested, and traverse the no touch barrier? Should I kiss her cheek upon greeting her, put my hand on her arms, etc?