Curious to find out where I stand but not too stressed about it

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    Hi everyone,

    It’s been a while since I have been here, but I wanted to get some insight into a situation with a woman that I met. The last time I was here I spoke about being on a dating site where a few different women have become interested in me. One was my age (43) with two younger children, and it seems like we chat, but meeting doesn’t seem like it will happen anytime soon. It is starting to seem like she just needs a man to talk to sometimes.

    The other woman is 35 and has 2 year old daughter. She was interested in meeting and we did just the other day. We had a pretty established rapport since we have been messaging since the end of July. She lives about 12 miles away in another town close by, so we meet in a town in between ours.

    It was a really nice date. We had a great conversation. She has a good sense of humour, and she was really down to earth. I found out that she grew up where I live, and we knew a lot of the same people. At the end of the date, I asked if she would like to go out again and she said yes. Then she wanted to give me a hug and it seemed like she was looking to kiss. It didn’t happen because this was pretty much the first date I had in 22 years and I was a little awkward. But man, I was on cloud nine. It was a great first meeting and I like her.

    This is where I need some insight. First of all, I made the topic title the way I did because I don’t want people to think I am obsessing or overthinking this.

    I texted her the next day, and told her that I enjoyed meeting her and complimented her. In her photos, she looks greats, but she looks even better in person. She messaged back that she had fun too and thanked me for the compliment. Maybe it was because she was still on my mind, but I complimented her again later. No response this time but no big deal. She has a life so I don’t expect it.

    I did send her one more text. Basically, I said that I know she is a busy fulltime mom with a career and that I know it’s difficult to get time to go out sometimes. Then I said that I am just trying to say that I like her and I would like to see her again, and I was going to leave it at that. Again, no response.

    I am not sure what to think of it. It feels like there is something there and she wanted to get close to me. I’m not sure if I am coming on too strong and maybe I shouldn’t message her for a couple of days. What would probably be best for me is to not think about it too much. I know on these dating sites, women get bombarded with guys messaging them, so maybe it was fun to meet me, but she is still looking at what’s around.

    Maybe I made her feel pressured.

    I might have to have a different approach with dating now. I use to wear my heart on my sleeve. If I liked someone, they knew about it, and I found it easy to compliment a woman.
    I’ll be honest, I am thinking about it but not obsessing.

    What do you guys think?


    Hi Steve,

    Your thoughts are very much valid…I share the same attribute..’I wear my heart on my sleeve’…Although I’m a woman, I prefer to say what’s in my heart rather than beat around the bush and play with mind (I’m bad at it :-))

    2 days ago I told one of my friends that I like him more than a friend, although partly I knew that he won’t be able to proceed and even if he has something for me, it won’t come out. And I don’t wanna burn myself this time by investing in a relation which doesn’t have a future. I prefer the other person be open and candid too. Anyways, it was just to share.

    When it comes to dating, the needs might differ, yeah? Some might be wanting just attention and sometimes women need someone to compliment them. If that’s all they were looking for, it won’t proceed further and believe me it’s better to not think much about why she didn’t reply you back (i am going through the same these days with the guy I like, so I can understand :-), it happens)….

    Keep a tab on your self-esteem and don’t let it go down in any case. You’re a wonderful human being and deserve a loving person. Whenever any thoughts come and eat your head…remind yourself to ‘Move on’…

    And as for the lady you met, if she is interested, she will message you back, have patience until then. Some people have a slow pace and we need to understand that. After all, it has to be mutual, yeah?

    Lots of positivity to you Trevor… Stay blessed!



    Yeah, you sound like you were a little blerty… but hey, your first date in 22 years went well and you were excited! You don’t really know what’s happening on her side, and its probably good to let it go for now. Give her some space. Maybe next weekend, ask her out again? Awkwardness is fuel for laughter, just own yourself, accept it, and she will too. Or won’t, but that’s a dealbreaker for me… we’re waaaay to fumbly and awkward to get hung up.

    Just a question, were both compliments about physical beauty? Consider the thought “hmmm, what does he think of me?” being answered by your compliments. Said differently, there’s wearing your heart on your sleeve, and then there is using your courageous heart. Rather than just blerting, like a startled “whoa baby, amazing”, we can temper that passion, and offer appreciation with a little more depth. Sure, her body is sparkly, alluring, but that’s only a part of her beauty, and not even the most amazing part.

    With warmth,


    Hey Matt,

    No, both times I complimented her wasn’t about her appearance. Personally, I would find it to be difficult to be attracted to someone who has nothing to offer but a pretty face. It was about her personality the second time when I complimented her.

    I can’t let this bother me because you can’t know what people are thinking. It possible that she thought about things differently when she left, I don’t know. I do know that it’s different than when I dated before. The other person and myself will have more responsibilities and less time. I guess there are lots of women out there. She just really struck a chord with me. It felt right. Maybe it still will with her. I’ll try to be patient.

    I went on the dating site again to check if anyone who messaged me today and it shows if people are online. The woman I met was online. I know that we have nothing right now, but she doesn’t respond to me, and she is online. It kind of just gives you mixed signals.
    If I felt that I could maybe work at something with her. I would be off of there immediately. I like to focus on one person, not a bunch of them. It’s confusing.


    HI Matt
    “Then she wanted to give me a hug and it seemed like she was looking to kiss. It didn’t happen because this was pretty much the first date I had in 22 years and I was a little awkward. But man, I was on cloud nine. It was a great first meeting and I like her”.

    Your actions didn’t follow your truth. Perhaps saying what you felt, “I feel awkward this is my first date I don’t want to mess this up, but I’m on cloud nine” would have connected her to you and to the moment. Clouding your feeling by pulling back and covering up your truth weaves that old web of confusion. Your pulling back wasn’t about what you feeling in the moment it had to do with what you brought to the table, you baggage, we all do it. Guess what? She brought her suitcases also and you have no idea what those bags contained. Perhaps in her past relationships her actions were “dismissed” or “scorned” and here it was happening again. She took a risk and it was rebuffed. This is all speculation of course. But what isn’t speculative is: you aren’t seeing clearly because there is nothing to clearly see.
    If you truly feel a connection…don’t give up, share your fears and reach out. Stay truthful and eventually the fog will lift.
    Good Luck!


    Hi Pamela and Matt, and anyone who wants to give me their input into what I am thinking of doing.

    I want to send her a text and this is what I am planning to say in it, and it is based on some of the things we talked about on our date. By the way, we shared the same circumstances of our previous relationships breaking up. We were both cheated on.

    This is what I want to send her.
    ” Hi, I just wanted to say one more thing. You said you get tired of people when you’re just texting them, and the novelty wears off for you. Your life is busy and you can’t sit on the phone asking, ” How’s your day?” I know it lose its impact after a while through texting.

    I don’t know how interested you are, but yeah, I’m interested I you, and I would like to get to know you better.
    I have never been a person who tries to get together with multiple people. If I meet someone who has something special about them, they get my attention.
    I don’t know if this is off putting or not for you. It’s kind of a damned if you do, and damned if you don’t situation for me. Basically, I just wanted to straight forward and honest with you. Enjoy the rest of your weekend.”

    that’s what I am thinking of sending. What are your thoughts?

    Big blue

    Hi Steve,

    A few thoughts:

    That would be a long text to send. A character counter puts it at half the length of the Gettysburg Address.

    “I just…” may not sound interested, authentic, or confident. I know what you mean about being honest, but you might be taking the fun out of dating by describing rather than being.

    How about something different! You said something about a sense of humor. Perfect. Use it. Invite her to something fun.

    Be easy on yourself. Be yourself. No matter what, take it slow. It will be easy for you to move too quickly in any dating for a while. What else are you doing besides looking online for dating?

    Big blue

    • This reply was modified 8 years, 9 months ago by Big blue.

    Well, Big Blue.
    Maybe I blew it then because I sent that message, and didn’t alter it at all. I’m trying to be patient but I think I sometimes want things to move quicker. I’ve definitely been overthinking now. She did send nice messages today but she kept it lighter than the one I sent at the end of the day. This whole online dating thing is somewhat annoying. I know there is not much between me and any woman I have talked with, even if we went out on a date, but you aren’t sure where you might stand if they are still online regularly.

    Big Blue, I took a leap of faith and told her how I felt about things. I am a sincere person and I wasn’t thinking about if ” I just” was good or bad to use. I don’t think anything I said was too terrible ,but I don’t know how other people think, especially women. If I received that message, I would probably think that the person listened to what I said, tries to understand what I have going on in my life, and that they are looking for one special person, and not playing any mind games with them.

    There was an ease about our date and I felt a connectedness that I haven’t felt with anyone in a long time.

    Now after sending that, I don’t know what to do. Don’t message her for a bit. Send her messages like this one didn’t happen. Ask her out again. Go on other dates too. A couple of other women keep messaging me, but I have this old fashioned belief that I am supposed to not do that, if I am trying to see what happens with this one.
    It probably doesn’t matter, she didn’t respond to the message I sent. I’m going to guess that I scared her off.

    I haven’t done anything as far as trying to date elsewhere. I don’t belong to any organizations and I am too focused on getting good produce to hit on women at the super market.

    If my chances are done, it’s a shame. She has a great personality, attractive, a caring parent, and she is a hard worker. I would still love an opportunity to get to know her better. It kind of feels like bearing a bit of your soul , and sharing something in a sincere and honest way isn’t a good thing to do anymore.



    Its not that being heartfelt is a bad thing, but perhaps honing those flirting skills a little, letting your inner flirt mature, grow up. Rather than “hey, we seem compatible, I am interested, I know you” which is pretty heavy, consider next time something aimed at helping her laugh, perhaps inviting her to something magical, something light. Less “construction mode”, more “sparkle mode”. 🙂

    Or, perhaps try to accept that if you don’t want that, that being so concrete and direct is just who you are, that’s fine. But you’ll have to wait for someone that is looking for a big meal, ready for that, rather than someone looking for an appetizer.

    Good luck!

    With warmth,

    Warrior of Light


    Be patient. Just breathe.

    In my experiences when people blast their raw, vulnerable, passionate, and sometimes insecure energy at me too soon into a date/relationship I tend to feel overloaded, shocked, and defensive… as in too much too soon. I believe Pamela made a valid point about unpacking your (past) baggage too soon. For me it’s off-putting to say the least.

    However, as the relationship develops, trust is formed, and you get to know one another I believe then it’s more appropriate to start showing the contents of your baggage to her; but again not too much too soon.


    Hey everyone,
    She messaged me back in the morning and thanked me for the message. She said she is a very slow mover so she couldn’t really say if she was as serious as me. She wanted to get together some more and see how things went. Then asked what the boys and I were doing?

    I told her that I don’t want to pressure her, and that it’s good that she doesn’t want to rush, because I don’t want to rush either. Also, I mentioned that we both have children, and that it’s best if we are careful about who we bring into their lives.

    WZ mentioned the about baggage. I don’t know how comfortable this means she is with me, but she told me a lot about how her engagement ( She told me she was together five years and was supposed to be married) broke up. It was too the point where I figured out a way to change the subject. She came off kind of aloof about it but I think she was hurt by how she was treated. I didn’t say much about mine. I was with my ex 19 years, and it was a painful raw experience that I didn’t want to relive for her.

    Also, maybe I show that I am really interested in a woman. That is something I will tone down, because I have a tendency to put my whole heart into a relationship. The other person knows that I am theirs, and they know that there is no one but them that I want.

    I know all these experiences are new again, and I definitely need to slow down and breath. Sometimes, it’s a little difficult when it feels so right for you. This woman is nothing like my ex-wife. She is like the person I should have meet many years ago.

    I am just going to relax about the situation right now, don’t overthink it, and see how it plays out. She is attracted to me and we had a good time together. If I’m uptight, nothing will grow from it.


    Hi Steve,

    If I may suggest, try contacting other women on the dating site, or even offline. I think, in addition to being relaxed with the situation, you also need to keep your options open. And probably focus more on other stuff (self-improvement, hobbies, etc) than waiting for what may happen with this woman. Just my opinion/suggestion.

    I wish you well 🙂


    Sounds as if you have a plan! Wonderful outcome. Try not to regret what has happened you weren’t the same person then, you carried a totally different set of inter personal skills in your tool box.
    Good luck!


    Hey Pooch ( If that even is your real name),

    There are two other women that really want to meet me. It is just annoying to get mixed signals from one that you built up a nice rapport with, and that seems like someone that you should have know, for a long time. Maybe it’s only me that feels this much.

    I texted her one more time that day. She never got back to me. Still hasn’t today so I’m not sure what is what. Plus, I went online a couple of times yesterday to check messages, and she is on there. It kind of messes with your head.
    I have talked to some family about it and they suggested that I let her get back to me. I’m thinking, “what if she doesn’t?” then do I get back to her again?
    Honestly, I’m too old for this high school crap so I don’t know what I will do. This is stuff I haven’t had to deal with for a long time, and I didn’t miss it. I guess I’ll be patient for now.

    Also, I’m actually thinking of going out with one of the women who want to meet me, but I’m a little tore about it. Wait and see if a woman you really like and have a rapport with will open up to you, or go out with other women, and maybe not feel on edge about the situation. It’s a struggle because I don’t want to hurt or use anyone.


    I’m going to be completely honest with myself. This is stressing me but I know, in my mind, that I am stressing over almost nothing. It’s over someone I hardly know, but I wish I had known, my whole life. Someone who wanted to meet me. Someone who spent a lot of time messaging me before that, and someone who wanted to be closer when we did meet. Now, she is someone who suddenly turned everything off, and is always online if I check messages there.

    Then I had a revelation. I fought for my marriage so much of time. I loved my ex-wife and I gave my heart and soul to what we were supposed to have. I gave 100% of myself to her and our marriage, right up to, and beyond the point where everything came crashing down around me. I was broken hearted and it took years to recover. I loved her deeply but I will never really know how much my ex loved me.
    It made me think,” Do I really want to go down that road again ?” not knowing how some feels about me, and stressing myself out about it.

    I know the reason that I am feeling strong feelings for this woman. She is the type of woman that I should have been with all along. She is as attractive on the inside as she is on the outside. She has a great sense of humour, and when I hear her talk about her daughter, I know she is a caring nurturing person. The problem is that I am getting hung up on her, when there are similar women out there.

    I don’t why she pulled away a bit. Maybe I was too eager sounding. Maybe it’s because she is a year removed from a breakup that saw her being cheated on by her partner, and the thought of actually giving yourself to someone else is scary. I wasn’t in any place to even think about dating then. Maybe she’s just not that into me.

    All I know is that, I am not going to try to force something that isn’t good for me again.

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