[Ty.webb]

Hi! I know I just registered, but I’m of the hope someone will be willing to read through my dilemma and share some advice. I apologize in advance if this goes long, but I’ll try to organize my thoughts.

I’ve been divorced for about a year & have been in/out of the dating scene. I have a young daughter that I share time with, but no real drama from the divorce/ex-wife. I head up a local company near where I live and I have a decent social life with some new and younger friends. I’m 40.

Anyway, recently our sister company hired this girl (about 25) who does not report to me in any way. About a month into her employment we really started to hit it off in a friendly kind of way. Emails, texts, etc. She had a boyfriend at the time so pretty much every chat we had was your typical safe conversation with maybe a very small amount of flirting. I always had a great rapport with her right off the bat & all of our conversations went really well as I can make her laugh pretty easily. We really became friends although I quietly started to like her more than that.

About a few months ago, she & her boyfriend started to have problems. Of course, I was there to talk with her and cheer her up. I was always able to bring a smile back on her face and she really relied on me to do so. Our conversations weren’t always limited to the work place. We have now started to chat on the weekends and text at all hours. It is here when the flirtatious messages have started to come into play. Naturally, they started with me but she has also done her share and included some very temping pics, but nothing too risky.

Flash forward to today. Her and I have bonded as we have a back/forth that most really would envy. We can not go even an hour without talking, emailing, texting, etc. We know lots about one another & i see we are compatible in what we want in a realtionship. All things couldnt be a better fit. She is broken up with her boyfriend & still a little hurt, so I am careful not to press too soon. However, I do throw the occasional ‘reminder’ that I am here & interested in more ways that just being a friend. I am very aware of the ‘rebound’ theory and don’t think I am at risk. I do though fear being trapped as the ‘friend’ and possibly overlooked when she emerges back into dating.

So, that leads me to my many questions. How long should I wait until the casual safe reminders need to be turned into blatant date requests? How do I assure myself that I am ‘next’ whenever she is ready? Is there an appropriate way to even ask that? Please know I have come to care for this girl very much and I am trying so hard not to press too soon, but I am cracking.

If only I knew she was just taking time to heal and that when she is ready she would look to me first. That information would set my mind so at ease & calm my fear of watching her move onto someone else. Part of me says that I have enough signs from her interactions with me, pic sharing, etc that I am not going to fall into the ‘friend’ category, but there is never a sure thing. I just like her so much that I want to make sure I am doing all the right things.

Can anyone help set me straight? How do I correctly help turn this into a chance to see if this can be the relationship I envision.

[April Masini, your AskApril]

[quote]How long should I wait until the casual safe reminders need to be turned into blatant date requests? [/quote]

You can ask her out now. It’s time.

[quote]How do I assure myself that I am ‘next’ whenever she is ready? Is there an appropriate way to even ask that?[/quote]

You can assure yourself that you’re next by asking her out on a date, and getting a yes in response!

I know you’re new to the dating world again, so let me give you a few pointers on how things have changed! 😉 First of all, dating is competitive — more than ever. Men and women have access to dates at work, at home and on the internet. Don’t assume you’re the only one she’s dating — especially before you have an established relationship with her. You’re going to have to win her over — and get out of the friend zone! But you can do this quickly and easily by starting to date her.

Because she’s someone you met at work, make sure to keep your relationship out of the office as much as possible so you’re not distracted at work, and if things don’t work out…. you’re not distracted at work! 🙂

I hope this helps. Please let me know how things go, and follow me @AskAprilcom on Twitter and on Facebook at this link: [url][/url].

[Ty.webb]

I appreciate your encouragement.

I guess I feel like I may have glossed over the fact she is still in a post-breakup depression. She still cries every so often since final closure was just recent. I think perhaps you may suggest a different approach now knowing that. Perhaps I’m wrong.

My personality is keeping from pushing too hard right now since she is in a fragile state as I don’t want to come off insensitive and only interested in my pursuit. Over the last few weeks, I have casually asked her to a few lunches, which she has accompanied me. However, the dinner/drinks and more ‘date’-like encounters I have asked her to have been met with a ‘not ready’.

Knowing that, do you still advise you press on?

[April Masini, your AskApril]

No. 😳 If she’s still crying, literally, over a recent break up, and she’s being very clear that she isn’t ready, don’t push where there isn’t a healthy relationship to be had. Find someone who IS ready to be in a relationship with you, instead. 😉

[Ty.webb]

I wanted to follow up on this to see if you can advise me how to back out of a jam and get myself back on track.

So taking your advice, I backed off as she was not ready to start a new relationship. I maintained my friendship and we communicate tons each day. I let her initiate the contact so I know it’s genuine and not just responses off of my texts/emails/etc. Anyway, it got to a point again where it just seemed natural to ask her out. I was again told that she is having a hard time getting over her ex. I knew I was upset and tried to get a hold of me later that night. Once I broke down and agreed to talk with her, she told me she feels guilty because she wants me in her life but until she can erase him from her mind that she doesn’t feel right leading me on. She did underscore ‘yet’ as if she feels the time will come. I felt better and continued being her friend.

Just last weekend, she told me she wanted to have a wine/movie night at my house. She stressed she wasn’t ready yet to be with me, but wanted to hang out with me. She also said that she wanted to make sure that I knew that in case we had too much wine, that she was afraid she may do something drunk that she wasn’t ready to do sober. I told her she could trust me and we would plan for a night soon.

Anyway, here is the jam I got myself into. I was online with my old Match.com login trying to get the emails to stop. When I did a search, I saw her profile and it was recently created. I was floored. Not because she is seeing what is out there, but because she has been telling me she isn’t ready while apparently being ready elsewhere. This got to me so much that I had her come over to my home after work where I basically opened up everything I have been feeling for her. I did not get mad about the online thing, rather I just wanted to know how much I felt for her and that it hurt to see that she was opening up elsewhere. She told me that some of my comments recently have scared her a bit and I’ve been pressuring her too much. She said if I keep it up that she may run from this situation.

I guess now I need to figure out the best way to relieve this pressure without being a jerk or totally cutting her off. She really has me confused right now because as I mentioned above, some of the signs to she wants to be together come from her. Telling me to have a wine/movie night where she’s afraid she will do something with me too soon tells me she is holding back feelings that are there. I could also give other examples and pictures she sends to me that aren’t exactly Facebook worthy. I am getting mixed signals, but then again have to see an active online dating profile!

I have fallen for this girl. Yes, I can go out with other girls and will. However, can you give me any advice to help start winning this girl over. I am aware there is no quick fix. I am aware I have to back off and bring her back out and reverse the chase. Yet, how can I do this effectively? I am willing to put in the time because I know the signs are there and this girl is amazing. I just need to get back on track. Can you help from that perspective?

[April Masini, your AskApril]

One mistake you made was agreeing to have her over for a “wine and movie date” where you were just “hanging out”. 🙄 You’re clear that she was sending you mixed messages….. but then you colluded in the mixed message behavior by agreeing to this type of situation. YOU have to stop sending her mixed messages.

I get a lot of readers on this site who write me about their getting mixed messages — and they don’t realize that they’re the ones who are sending the mixed messages back! You’re in good company! 😆

So take inventory: It’s pretty clear you want to date her. Be honest. And don’t agree to be friends or to hang out. If she’s not ready to date you, then back off. All the way. You can invite her to go out on a date, but don’t fall for the friend zone — especially knowing she’s testing the waters elsewhere (remember I told you this in my last post to you??) on internet dating sites.

She may or may not be interested and/or ready to date you — but YOU have to be clear on your stand towards her. 😉

I hope that helps. Please let me know how things go – and follow me @AskAprilcom on Twitter and on Facebook at this link: [url]]. 😀

[Ty.webb]

Thank you and I will give it a try.

In fact, I tried today but she was upset when I was not talking with her as much. She actually got pretty mad at me by noon. I realize there needs to be a tapered pull back, but it will be hard as she is usually on to me by hour 1. I’ve tried it before. 🙂

You are right though. I need to give her space as just today she was still down about her ex. I must pull back and give her a sense what it is like without me there either knowing there is only one way I will return and that is romantically.

I’ll let you know… Thanks!

[April Masini, your AskApril]

You got it! 😉

[Ty.webb]

I got it. It is just frustrating that everyone must play some version of a game, no matter how great the people involved.

One final question, would you take it that she is interested down deep given the signs? I just can’t believe someone would initiate conversation as much as she does (even after I tell her exactly what I want out of our friendship), send riske pics, talk about being worried about doing something sexually with me before she’s ready, etc etc. I only ask this question because the natural rule is to take the ‘I’m not ready’ response as a gentle ‘no’. However, with the other factors involved – it seems inconsistent.

What are your thoughts?

[April Masini, your AskApril]

[quote] It is just frustrating that everyone must play some version of a game, no matter how great the people involved.[/quote]

You’re not a victim. You don’t have to play any game at all. You get to make the choices in your life! 😀 You can do whatever you want.

[quote]One final question, would you take it that she is interested down deep given the signs?[/quote]

Not necessarily. And besides, what you think she’s interested in, may not be what she’s interested in. She’s looking for fleeting attention. You’re looking for a relationship.

[quote]What are your thoughts?[/quote]

Gosh…. I’ve certainly given you my thoughts here! I think you don’t like them, so you’re hoping for a different outcome. Sorry! 😕

[Ty.webb]

No, I’m with you. The ‘your thoughts’ part was actually just another reference to the question above & not a request to reexamine. I agree some of it is for fleeting attention, but I know she really wants it (my attention) and it’s very obvious she misses it a lot when it is not there. So, now is the best time to pull it from her to get her to want it back permanently and more so on my terms if she chooses it’s that important to her.

I’m going to hang in there & try to gradually phase out, so I can make a better comeback when she is ready.

Thanks again!

[Ty.webb]

Hi April

I asked for your advice a while back and would like to see if you could help here.

To quickly summarize, I had a friendship with a co-worker blossom into something more. While it never went into a full on relationship, we connected and have strong feelings for one another. Well, about 6 months ago I tried to push for that relationship to go to a committed level and it didn’t turn out. I got mad, walked away, and she went back with her old boyfriend.

About three months later, we started talking again. That ‘talking’ turned into some strong flirtation back and forth. It got pretty heavy up until she said that it wasn’t right and it needed to stop. I became upset about being teased and then backed-off, so I went into extreme no contact for a month and refused her many attempts to reach out. During this time, she was sent home a few times crying due to me refusing to even say ‘hello’. I could tell she really cared and missed me, but I didn’t crack. I made it clear when i last spoke to her then the only way we were going to be together is by relationship and NOT as friends and not to ever speak to me unless she was prepared to move forward,

Well, about 3 weeks ago – she wrote me a long message saying she loves me and thinks about me all the time. She realizes she made a mistake and hates the situation right now. Once again, she broke down in the office when I turned away from a chance to say hi. I felt so bad that I put some flowers on her desk before she got in the next morning with a simple note saying ‘sorry’. The next day, she sent me a text saying how much she misses me and I started to chat back. During this, she revealed once again she loves me and needs time to fix this situation because she hates being away from me. I agreed to give her time, but made it clear what I expect.

She now is in the process of breaking up with him. She doesn’t hate him, but it wasn’t right. Everyone tells me to give her some space to do this and not to expect a relationship to start up with me instantly as it will still be tough to leave the other guy. The process has started, but I am getting annoyed with how quiet things have become. I guess I was expecting a more dramatic turn of events where we would be closer now, but it seems opposite. Once again, I know it’s still difficult for her and I’m trying not to pressure – but I feel like I am being out on the back burner despite all these feelings she revealed to bring me back into her life.

So, am I doing the right thing by not pressing? Should I give her space during all of this? What can I do to keep myself from going nuts? I don’t want to ruin all of this, but I don’t want all those feelings to be forgotten during this time. She doesn’t want to talk about it when I ask and she says she is so stressed over it all. All she asked that I give her time and we will figure it all out once her current situation is resolved.

Any thoughts? I do LOVE this girl, so I’m trying to do this right and give us the best chance.

[April Masini, your AskApril]

[quote]So, am I doing the right thing by not pressing?[/quote]

It depends on you! Most men would try to ask her out on a date and woo her and win her over. That’s what I’d been advising you when you wrote here back in March. Your interest in this woman are almost a year old now, and it doesn’t sound like you’ve ever dated her. 😕 Giving her an ultimatum that she has to either be in a full scale relationship with you or not is a little risky. You’re trying to prevent yourself from being hurt by guaranteeing her commitment. It doesn’t work that way. Dating is competitive. 😉

The problem with ultimatums is that they’re very black and white, and since you told her it’s all or nothing, you got nothing. And now you’re second guessing your method. 😕

[quote] Should I give her space during all of this? [/quote]

My advice was to try and win her over by dating her. If she isn’t interested in dating you, then move on. Since you gave her an ultimatum, your choices are to stick to it, or cave and change your mind and start dating her.

[quote]What can I do to keep myself from going nuts?[/quote]

Look elsewhere for Ms. Right. Date other women. Don’t put all your eggs in this basket. You’ll be a lot more attractive if you’re desired elsewhere.

[quote] I don’t want to ruin all of this, but I don’t want all those feelings to be forgotten during this time. She doesn’t want to talk about it when I ask and she says she is so stressed over it all. All she asked that I give her time and we will figure it all out once her current situation is resolved.[/quote]

I’m not sure what it is you’re afraid of ruining. 😕 She’s dating someone else, and she’s young. She’s only 25, and she doesn’t have a lot of experience, and she’s been crying, according to your e-mails, off and on since last February! 😳 The problem is that you gave her an ultimatum, and then didn’t stick to it. I never advise ultimatums…. 🙁 If you really mean what you said, that it’s all or nothing, then you have to back off and move on with your own life without her. If and when she does break up with the guy she’s seeing, you’ll have a shot at dating her, but remember that dating is not marriage. And even marriage, as you, a divorced dad, knows, is not an insurance policy against heartache. 😉 Just because you date someone doesn’t mean that there is not competition. Dating is a process where you get to know someone and decide during that process, if you want to continue investing in the relationship. 😉

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[Ty.webb]

The only reason I broke this ultimatum was due to her crying and messages that she loved me and realizes she made the wrong decision. While I know that isn’t a ‘we are dating now’ statement, combine this with telling me she is going to leave the current guy for me gave me enough to start talking with her again. She knows I would have not returned talking with her if it wasn’t the case. Also, to answer, we did actually go out for a time – been intimate – and I was even introduced to her parents right before I pushed for the exclusive.

This is not the same as before where she was crying off a long term relationship. This time it was a short relationship that started late Spring with someone she used to out with. She says she now realizes she should have been with me all along and it was wrong to have started this up with the current guy – who was a close long-time friend. So, maybe I am almost glad she had a ‘rebound’ relationship to clear her head, stand back, and see who meant the most. By her words, it was me.

Now, I am trying to give her space to complete this break up that started recently as promised. There is a lot to it since they all have the same friends and she even stayed with him off and on during the week. Of course, I want to say forget all of that and let go out – tonight and begin what we both have been talking about for the last 3-4 weeks which is being together. However, I can tell she is stressed over all of this and I guess I don’t want to make a similar mistake as before by giving her a time ultimatum.

I’m scared to pressure. She has always been a person who runs from it. I want her happy and not forced to hurry up. Yet, some days it just kills me to stay quiet and not say ‘where do we stand today’.

[April Masini, your AskApril]

I didn’t realize before your last post here that you’d dated, been intimate and met her parents. 😮 Thank you for that information!

However, it doesn’t add up that when she says she loves you and wants to be with you — she doesn’t break up with her boyfriend. 😕 You and I both know, a break up can happen in one one meeting — and worst case, on the phone. But it doesn’t have to be drawn out, and she clearly has feelings about this other guy or she would have broken up with him already. 😕 You need to remember that when words and actions don’t match up, trust the actions.

My advice is to move on with your life, and if she breaks up with this guy, you can date her, but right now, she is sending mixed messages with her words and actions, but clear ones with her actions. 😳 She may say one thing, but she’s doing another.

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