Should I ask her out?

[Metatron]

I have been out of the dating came for over 11 years. I want to ask someone out but am very unsure about taking the risk. Here's a (not-so) brief history that got me to this point.

I was always a little shy around girls growing up. I looked several years younger than my classmates and could never connect with any of the girls my age. I definitely learned a lot of confidence in college and was able to date a little bit. I would meet girls through friends or at bars, but could never get a serious relationship going with anyone.

After school I moved to a new city and found a girl I really liked. After a long chase, I got my first real girlfriend and we dated for 10 years. The first five years of our relationship were great and my confidence was through the roof. The last five years consisted of her rejecting my marriage proposals and pointing out my seemingly inconsequential shortcomings daily. She broke up with me a year and a half ago. Probably for the best.

For the last year and a half since the breakup, I have done everything I could to build my confidence back up to where it was in the early stages of my relationship when I was happy every day. I said yes to ever social oppurtunity and have met dozens of new friends. I have accepted myself as a good and decent person. I have tried to ignore the physical faults I can't change, and work very hard at the ones I can. It has been a long road, but my self esteem is slowly coming back.

The one area I haven't moved forward in is dating. I am now thirty five years old and have no idea how to get back into a relationship. I have been told the best way to get used to dating is to just constantly date. I feel like my self esteem has been built back up, but is too fragile to handle rejection. I'm so afraid to go back to the person I was over the past few years.

There have been 3 or 4 women I've met over the last year 1/2 that I would be very excited to date and would risk asking out. One had a boyfriend and 2 had absolutely no interest in me.

There is one girl at work I have recently met that has attracted my attention. She sends my confidence level as high as it ever was (almost cocky sometimes). She seems fun, smart, pretty and though I'm usually horrible at picking up on it--I think she has been flirting with me. I have been flirting back and would like to ask her out before she stops working her temporary position at my office next week. One problem is that she is 23 and I am 35. I usually have no interest in girls that much younger but she seems really fun and mature.

I asked her to a happy hour yesterday that she seemed excited about, but at the last minute she went home instead. I started to doubt her interest in me and mentioned it to another co-worker. He told me that he didn't blame her because I was too old for her.

Anyway, that is my dilemma. Should I take a chance before she leaves next week and ask her out? Or is that age difference creepy? I have no idea anyomore. I have been convincing myself that I am misreading the signs and there is no way she would have any interest in me, but then I think that's the old "safe" me talking. I just feel like I am so terrified to take a chance on anyone these days, that maybe I should follow through with the ones that inspire me to. Aaarghhh.

Any specific or general advice would be much appreciated.

[butterflyeffect]

Hey metatron,

I think you should seize the day and ask her out again, just for coffee or something casual and chat to her. That way you will know for sure whether she is interested or not.

The situation as I see it.

Positives:
- You like her
- She is single, your single
- Your confident, always good.
- You have chemistry
- She is just at ur office for a little while, no awkward office politics problems


Potentials:
- A fun date
- Chance to get to know someone new
- Learn to better understand modern dating
- Increase confidence
- Gain further understanding on the signals people send out and reading them.

Concerns:

- You may get turned down.

- The age difference may be a problem depending on both your views and personalities.

** Anyway, Im 21 and I often get asked out by older guys. I'm not sure if its because im soo mature or they just like me. Sometimes I like them other times not. The difference is with the people I like I will stay friendly and chatty, but if I don't want the attention, my voice will become high pitch, I'll fiddle with things, play with my jewellery, edge towards the door, clench my hands and keep a fake smile plastered on my face, while making reasons I need to exit. I will keep as much space between me and them as possible, like stepping back, keep glancing at the nearest exit and eyes not calm and focused on them. So if people behave as above, usually its safe to say thats a no.

[lookcloser]

I think you have to work on your fear of rejection. Why do you feel that your value somehow goes down when you face rejection? Its impossible in reality because we are all whole and here for a reason.
Also you can think of what life lessons these situations are teaching you? Do you see a pattern in what's going on? Recognize the pattern and do things differently this time. You are an explorer in this dimension and your physical identity is only an avatar used to experience the various life lessons in this reality, its not the real You.

Maybe you have faced rejection before because you had to learn to love yourself unconditionally and be completely comfortable in your own skin. I can totally understand what you are going through because even I used to hold back a lot in the dating world because I was afraid of everything that could go wrong, and I didn't have the courage or confidence to be able to collect the pieces if something did go wrong. But this only made me lifeless and dull. So I decided to go out there and get HURT! Although I had this mentality things seem to be turning out okay.

So if you like this girl ASK HER OUT! Its not like there is just ONE woman out there. Heck, they say every person has SEVERAL soulmates. Go forward with anticipation and enthusiasm and the universe will be your wing man

[TonyToneTone]

Yes.

[Andrew Brunelle]

What is the worst-case scenario about asking her out? If you can live with what you can imagine as the worst-case scenario, then ask her out. If not, don't. Weigh the pros and cons and make a decision. The choice is up to you, but you have to live with that choice.

[180]

About the flaking out.

Lots of reason why women flake out.... One of them, is to test the persons interest in her. She wants to know how far you will go for her and to see how you will react in the situation.

Or she genuinely just didn't feel like going. Don't let that be a reflection of how much she likes you or not. I know women who flake out all the time. Some of them were ex's and some of them are still my friends.

It depends on how they feel (So yeah I'm a little bit cynical at times when I talk about women and how they feel. lol) A woman can be interested for a little bit. But then suddenly if she's just not in the mood. She won't go. Don't worry about it too much.

GTG I'll come back

[Maru]

Ask her out, and if she turns you down, then immediately go talk to 30 other women.

[Metatron]

Thanks for all the advice. You guys are great. I have subconsciously come up with a hundred reasons why I should play it safe and not talk to her, but in the end I would be really mad at myself for not trying. If the worst that can happen is that she thinks I'm weird or too old, I can live with that.

I have already confirmed with a mutual friend today that she definitely doesn't have a boyfriend, so the only thing holding me back is me.

Er, but now that I've decided to go ahead with this, I realize I haven't had to ask someone out in ten years. I usually don't need this much advice, but I'm not sure the best general approach. I probably won't physically see her for more than 2 minutes this week before she leaves, and she won't be alone. We are all working at some crazy convention.

I would hate to ask her out through facebook or e-mail, but I don't know if I'll see her long enough in person before she leaves the company. Should I be direct and ask her if she wants to go out on a date (making sure to use the word 'date")? Or do I keep it vague and say something like "we should go for coffee sometime".

So what do you think? Definitely in person, or is an e-mail acceptable in a pinch. Direct or casual?

Thanks for all the help

[butterflyeffect]

In my opinion, I would ask her in person if she wants to go for coffee at a specific time, e.g. "Hey, do you want to come grab a coffee with me this afternoon?" Or "Can I take you to lunch on Friday?"

That way you are being direct, will allow her to respond and she may say yes, no or ok but a different time would be better.

If you say 'sometime' it can be vague and just not end up happening, like "Oh yeah we should get a coffee sometime..." those particular coffee tend to remain elusive in my experience.

EDIT. Email would be fine in a pinch but I think you will get a better response if you ask her in person. Don't say date, just keep it casual, like coffee or lunch, drinks after work.

[Metatron]

My plan is of course to ask her out before she leaves our company this week. I found out she is leaving thursday instead of friday so I needed to expediate my gameplan.

I perseverated about messaging her for the first time through facebook (I seem to go from super confident to painfully shy in a heartbeat). I did, and we wound up chatting for two hours. Maybe I'm blazing a trail into the "friend-zone", but it sure didn't feel like that. She found out she was going to be in the same location as me tomorrow and we'd get to see each other.

I thought I should quit when I was ahead and say goodnight first, but I was having too much fun and stayed on a little longer. In the last two minutes I randomly mentioned some guy at work in a story (the guy is around her age), and she mentioned how cute he was. It crushed me right at the height of my glory! Blechhh

Must....stay....positive

[Maru]

we wound up chatting for two hours. Maybe I'm blazing a trail into the "friend-zone"

You probably should ask her out ASAP. And then, go talk to 30 other girls in the same day as soon as you can, whether she accepts or not.

[180]

Just I'm curious... you aren't calling yourself megatron out on dates are you?

I heard a story about this teacher who legally changed his name to Optimus Prime.

At a dinner with all these teachers, there was one girl that he really liked. He kept talking slurred because he was drunk (in a robot voice too I heard). And kept making the moves on her.

Finally, he tried to put his hand on her leg. She screamed up and called him a pervert.

He exploded and was like "DO YOU KNOW WHO I AM? I'M OPTIMUS PRIME!"

True story.

[Metatron]

Maru:
I see a pattern to your advice and I can't find any fault with it. Unfortunately, talking to girls has never been my problem. It's getting anywhere romantic that is. I can talk to anyone when i really don't care what the outcome is.

180:
It's Metatron actually. Didn't really put too much thought into it. He's supposed to be some sort of celestial scribe/ angel. He's also a bad-ass in the His Dark Materials novel series.

Can't believe the Optimus Prime pickup line didn't work though. It sounds like gold!

[180]

Originally Posted by Metatron

Maru:
I see a pattern to your advice and I can't find any fault with it. Unfortunately, talking to girls has never been my problem. It's getting anywhere romantic that is. I can talk to anyone when i really don't care what the outcome is.

180:
It's Metatron actually. Didn't really put too much thought into it. He's supposed to be some sort of celestial scribe/ angel. He's also a bad-ass in the His Dark Materials novel series.

Can't believe the Optimus Prime pickup line didn't work though. It sounds like gold!

Oh my bad I thought Your name said meGatron. like from transformers...

lol

[butterflyeffect]

So tomorrows D-day, her last day at the company!!

Why not ask her to join you for a drink after work? A personalised leaving party.

[TonyToneTone]

Originally Posted by Metatron

Maru:
I see a pattern to your advice and I can't find any fault with it. Unfortunately, talking to girls has never been my problem. It's getting anywhere romantic that is. I can talk to anyone when i really don't care what the outcome is.

Talk to her like you would if you weren't attracted to her.

[SheldonCooper]

Worst case scenario: she says no. And you'll live as always.

[Metatron]

So for better or worse I did it. Not all that well, but she said yes.

We worked a convention together today and we texted a few times. We had some alone time at the end of the day and she said that today might be her last day so I had to act quickly. Then a co-worker sat down with us and started talking about god knows what. When she got up for a minute, I made it politely clear to him that it was time for him to go. He left. I asked her if she was going to be around this weekend and she replied "Yes, I live here now". Guess she thought I was confused about that or something. Then I asked her if she wanted to get together saturday. She looked a bit surprised and said yes.

Then some of her coworkers came and she had to do something. I went on ahead to our catered dinner and started talking with my friends. She came with her own friends a few minutes later and started talking with them. She wound up having to cut back in front of me in the dinner line to get napkins. I made a joke about her taking half the napkins (which she did) that normally she would have laughed at. She nervously mumbled something about her table needing them and walked away. No eye contact.

I'm terrible at reading women. The shy part of me says she is not interested and was surprised into saying yes. The confident part says that she herself might be shy because I just asked her on a date.

I also should have been more specific to when and where. The "date" seems kind of vague. I messed that part up. i just kind of said what came to mind, and apparently specifics were not a part of that.

Anyway, my goal is to try to make a specific plan for saturday night. I haven't decided dinner or drinks (or both), but I think I should figure that out fast and either text message her or tell her in person if she actually is in the office tomorrow.

I think if she makes an excuse to back out, that is a sure sign I should keep away from her.

I don't know what's going to happen with this, but in the very least and for the time being, I got past a barrier that scared the hell out of me. I wanted to ask her out and I did. Poorly perhaps, but rome wasn't built in a day and as several of you are telling me, there are other fish in the sea.

It is so rare that i meet anyone that i am really excited. That's why I'm putting too much pressure on this.

I want to thank all of you for helping me. I will happily take any more advice you may have to offer. Sadly, my gut tells me she will cancel out of this, but i will let you guys know.

[180]

She could be faking you out.

My ex-girlfriend used to do this kind of thing.

when we were dating I used to ask her out casually and she was so.... "Ohhh ... ummm ok". And be all weird and uncomfortable. Seemed like going out with me was like touching a leper or something.

She later asked to go to my home and jumped in the sack 2 hours later.

"There more than meets the eye"

Yes I know you're meTatron.... but I'm staying with the transformers gag as long as I can.

[butterflyeffect]

Quit fretting, you asked her, she said yes. Its all done.

Unless you are a mind reader then you can't know whats going through her mind and guessing is just going to make you feel bad and put a downer on your whole evening.

Forget dinner, waay to formal, you end up making polite small talk and trying to eat at the same. Stressful!! Ask her to meet you for cocktails/drinks at a low key bar with dancing near you both. Then have a couple of drinks, chat and dance and see what happens.

Plz relax, you have done soo well. CONFIDENCE!!! Go for it. We're all gunning for you.

[TonyToneTone]

You texted with her? Does that mean you've had her number this whole time?

[Afro Boy]

I've just stumbled on this forum and read your thread. Well done on asking her out!

I agree, something relaxed and easy going is probably your best bet to start with. Having an activity or other people around can also help diffuse some of the tension. Remember, you can always find a couple in the bar and play the game of making up what they're saying to each other!

At any rate, it seems like you both get along with each other quite well so I'm sure it will all be fantastic!

I wouldn't worry too much about her sudden shyness. Remember, all of a sudden she knows that you know that she likes you. And she knows that you like her. It makes people a little self-conscious so I would say it's perfectly natural. Just like you fuss over what to say, she is probably fussing over similar things in her own mind.

GO FOR IT and don't forget to keep us updated.

Cheers,
Af.

[Metatron]

Yeah Tony, I invited her to a happy hour last week and she wrote out her phone number for me and said to text her when I was going over. So yes, she gave me her number, but with texting it doesn't mean the same thing as it used to.

Today was her last day at my work.

I saw her briefly today and she seemed a little quiet and uncommunicative. I had been asking two friends of mine (male and female) what I should do for the first date. They gave me a bunch of "you MUST do this", you have to say things "exactly like this". It was driving me nuts!

In a moment of clarity, I threw everything they said out the window. I knew a comfortable place to take her where we'd have a good time and decided to forget all the other nonsense.

I called her knowing what I wanted to say. I figured that the ambivalence that I was reading off of her either meant she was interested and shy, or uncomfortable and uninterested.

I figured if she wanted to avoid me she would just let it go to voicemail. I called early enough where she wouldn't be asleep and her recent facebook update (which she seems to do every 20 minutes or so) said she was at home.

So....she didn't pick up. I left a confident brief, message saying hi and seeing if she was still interested in doing something this weekend. Gave her my phone number (which she had anyway) and told her to give me a call when she wanted.

I guess there's a slim chance I could here from her tomorrow, but reality tells me that this is the end of my little adventure.

At the very least, I'm glad I did this. It's very hard for me to think about dating or asking someone out after being in a relationship as long as i was, but I guess you can't get there without practice. I'm proud that I at least made the step and hopefully the anxiety will lessen every time I do this.

I'm definitely disappointed in the situation, but happy with myself. Too bad, she seemed really cool.

I want to thank all of you who helped me this week and offered words of advice. Thinking of some of the things you said really boosted me up and gave me the confidence I needed.

Thanks again

[Metatron]

Here's a little post script. It felt like this thread needed the rest of the story after all this.

She was in fact blowing me off. I'm not really attracted or excited about many people (I know--I need to fix this), so I found myself regretting the loss of her as a friend almost as much as I regretted the date rejection.

I really had enjoyed talking to her as much as I have lately and felt badly that we were just going to ignore each other from now on. Although I'm sure most people would say to leave the current situation alone, I decided to write her a short message telling her there were no hard feelings and wishing her the best of luck in her future.

She immediately contacted me. She apologized and said she was really sad about the situation and felt like she didn't handle it well. She just wanted to be friends. We talked for about an hour and things seem to have gone back to the way they were.

In the end I didn't get the girl, but I actually am glad to have her in my life. I definitely feel better now and will hopefully find someone else to ask out soon.

Thanks guys

[butterflyeffect]

Your attitude us really positive and Im glad you guys are still going to be friends. I think you have handled the situation well. There will be other girls and you haven't lost anything from trying.

Keep us updated when you ask out the next girl. We are all here for you. xx

[Gene]

Originally Posted by Metatron

In the end I didn't get the girl, but I actually am glad to have her in my life. I definitely feel better now and will hopefully find someone else to ask out soon.

Thanks guys

I really enjoyed reading of your adventures as you worked through your desire to ask your friend on a date. I would however say that you do have her in your life but as a friend rather than in a romantic way. Friends are awesome and the fact that you could take the risk of talking to her is real courage and led to the ability to keep her as a friend.

[Maru]

Well played.

Since you are still on good terms with her, next time you hang out let her know you're still looking for a date. If she's your type and she's a cool girl, there's a chance she could hook you up with one of her friends who's probably similar to her.