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I messed it up with her on the big date, we are friends now, should I try again?

Tagged as: Dating<< Previous question   Next question >>
Question - (7 January 2008) 5 Answers - (Newest, 30 January 2008)
A male United States age 41-50, anonymous writes:

Hi all,

First, my apologies for this being so long!!!

I met a girl online via one of the dating websites last March, she was just finishing law school and studying for the bar exam at the time, so we only had 3-4 emails between us until we finally met in August. We went out on a couple of coffee dates and I thought they went ok. Right at this time, she was right in the process of moving, so I helped her move when her movers didn't show up. We happened to have our first dinner date (third date overall) on the second night of helping her move. She wore an amazing dress showing off her body in a tasteful way, and I got nervous and didn't know what to say to her after dinner ... I couldn't even make small talk. It sucked and she ended up avoiding me for a week, and then told me she didn't feel the chemistry between us, her friend told her he liked her, and she had too much going on (new apt and new job) going on. We decided that we could stay friend and keep in touch.

Fast forward to mid November, just out of curiosity, I sent her an email to see how she did on the bar exam. She texted me back and let me know she would get the results in a week. The day she found out she passed it, she texted me. A couple nights later she texted me and said she passed out, so I called to see if she was ok, and she was. The next night, she went out to celebrate and texted me at 1am to see if I could drive her home. I texted her back and said I could if she couldn't catch a cab. Well, two days later, we chatted online and it turns out she was drunk that night. She also texted me and told me thanks for caring about her and she appreciates it.

We've chatted/texted each other a few times a week since. One night she was really pissed off at her roommate, so she let me know how she felt about her roomie and how she needed to move out.

We were supposed to meet up for dinner to catch up, but over a three week period, she got sick for a few days, then I got sick for a week and a half, and then she got sick for a week! (Sidenote - A lot of people had the same exact symptoms.) So we never got to meet up.

I got bored one day and wanted to see a movie. None of my friends wanted to go, so I just texted her to see if she saw the movie. (I don't really know why I did that.) Anyways, she offered to go see it with me and then she wanted to go that evening. So, we went to see the movie together. I found out her computer was broken, so I offered to try to fix it for her that night. I got it fixed and while doing that, we got a lot of small talking in. (Keep in mind how I didn't do that previously!)

She went home to her mom's for 10 days (for the holidays) so we didn't chat much during that time.

Last Saturday night, we chatted for 3 hours. She asked if I wanted to go see a movie and then somehow she asked if I wanted to have kids one day. I told her yes, but I didn't think I'd ever find someone who liked me, and she told me not to think that, and specifically mentioned that we met online and we're still friends. I ended up asking her why did she have to bother with online dating. I told her she's hot and should have a line of men waiting to ask her out on a date. She told me that most guys thought she was snotty or were afraid of talking to her. She also told me how she's old fashioned when it comes to talking to guys (she doesn't usually talk to them first) and doesn't believe in asking men out.

Anyways, she told me told me she's thinking about trying online dating again, but doesn't have the money/budget for it, so she's just going to trust God on this one ... so in effect, she told me she's single and wants to date.

Ok, so after all that, do you guys and gals think she might be interested in dating me again? My gut instinct is yes and I think I should ask her if she wants to try dating again, but I'm afraid that if I'm wrong, I'll just end up scaring her away. Any advice would be appreciated and thank you for reading!!!

View related questions: drunk, met online, money, period, roommate, text

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A male reader, anonymous, writes (30 January 2008):

I forgot one last thing - for her, this was another episode of having a friend telling her that he likes her! So, it turns out that she has a pattern of misleading men.

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A male reader, anonymous, writes (30 January 2008):

Hello everyone,

Well, I asked her if she wanted to try dating again, or if she just wanted to stay friends. She said she just doesn't feel like being in a dating relationship with me ... at least she doesn't feel that way right now.

Yeah right, basically she said in a nice way that she will never consider dating me again unless I'm the last man alive, then she'll give it some thought. I had a bad feeling that would be the case since she keeps talking about guys she finds hot lately. Oh well, it's better to find out now than to continue wasting money, time, more money, and energy on a dead end relation!

- OP

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A male reader, anonymous, writes (8 January 2008):

Hey Collaroy,

Well, according to the online site, we were matched up because we were compatible. We did talk about the date, and that's when she told me about the friend who told her he liked her too, how my silence that date was weird, how she didn't feel the chemistry, and that she was going thru a very busy phase in her life.

Anyways, I asked her if she'd like to go see the movie we talked about and have dinner, and she said yes! My plan now is to kiss her at the end of the night and see how she reacts.

- OP

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A reader, anonymous, writes (8 January 2008):

This one has so many variables that it would be hard to point out the answers.

You mind as well put it out on the table. If she wants to see you, she'll tell you. If she doesnt, she'll most likely want to still be "friends" I always hated that. I am dealing rightnow with a horrible situation from an online chance meeting. The apple of my eye is quite a bit younger, but just the same, I laid it all out. she finally responded affirmatively but got cold feet and broke off contact THE DAY that we were setting up our meeting. You have the luck that you have gotten to meet your lady. So all I can say is just give it a shot. If you scare her away, she wasnt worth your time

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A male reader, Collaroy Australia +, writes (8 January 2008):

Collaroy agony auntMate,

you got to ask her out. Otherwise it will simply eat you up inside. You are looking for a relationship and so is she, if you are not compatible there is only one way to find out, start dating.

If you carry on as you do, she will invariably meet someone else and then where will you be.

My suggestion is talk to her about that first date. Say to her you got tongue tied as you found her extremely desirable and couldnt focus. Beleive me she will find this very flattering.

Ask her out, if she doesnt reciprocate then you should move on. Having a female friend is perfectly fine, but you are both looking for a long term partner why so beat around the bush? The friendship will only go so far and will lead to jealously the moment one of you finds a partner.

The way i see it, you have nothing to lose - tell her how you feel - and just dont hold back.

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