_westendgirl_ is offline _westendgirl_ Post #1  December 22,2011, 11:04am
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I wanted to get some thoughts on something.

I was matched with a guy on eH in late November. I initiated 1st Questions. We moved through GC and into OC within a couple of days and then exchanged personal emails and set up a phone call. We spoke on the phone and during the conversation I found him to be nice but also shy.

We come from similar backgrounds (both farming families, both working now in the city) and I am used to shy men from this background. Not that all farmers are shy - but often they have a lot going on in their heads but not a whole lot to say. My dad and two of my brothers as well as my grandfathers were like this. That being said, while I am comfortable with shy men in my life - I have never actually dated or tried to date someone who was shy! Anyways - at the end of the conversation he said casually "we should meet for a coffee sometime". Perhaps at this point I could have said "yes, what about x day?" but I did not....I think I just didn't think about it at the time. This was on a Monday night (a week after matching).

We emailed a couple of times during that week. Just short emails - how are you doing? how's your day etc with either him or I initiating the emails. I had hoped he would ask me for a coffee. When he did not by that Thursday night I emailed him to ask if he would like to meet for a drink on Saturday evening. He immediately said that he would love to.

We met for a drink. He gave me a nice hug when we met and a big smile, we sat for about 2 hours talking. He told me himself that he was shy but less so than when he was younger (he is 52 and I am 45). When the bill came I pulled out my wallet to pay (since I had asked him to meet) but he declined and paid for the date. We parted at the parking lot, he asked if I would like to see him again and I said yes. He gave me a very nice hug again (full contact) and although there was no kiss I was happy with how it ended.

The following day I emailed to say thanks and that it was very nice spending time with him etc. I also said in this email that I was looking forward to seeing him again and to let me know when he wanted to get together. he emailed back to ask what my schedule was like (are week nights okay or weekends better - since I am a single Mom). I responded to that and then after that the emails didn't refer at all to seeing each other. No follow up on that for the next week. He went away on business and to be honest I was thinking that he had lost interest. his emails still came each day - short and to the point but still asking how my day was going and sharing a little bit about his day/week.

About two weeks after our first date (on a Monday) he emailed me to say that "he had hoped that we could have seen each other that past weekend". It was funny but it made me think that he was too shy to come right out and ask me out - that maybe after such a long time between meeting he wanted to gauge my interest level. So after getting that email I said 'well why not this Saturday evening?" His response was that he had a holiday party to go to that night but what about Saturday or Sunday afternoon. I agreed and we met for lunch this past Saturday.

When I saw him he again gave me a big bright smile and a big hug. We had a really nice lunch and he was much more at ease and comfortable. There was a wee bit of flirting on my part which he seemed to like. I decided that I would pay for this date and he was pleasantly surprised I think by this.

At the end of the date we again walked to the parking lot - my car was parked further away than his. He kind of stopped midway and gave me a big hug and kissed me on the cheek. I think he was going in for a real kiss but I overshot my hug and we ended up doing the cheek kiss. Then he looked kind of sheepishly at me and said that we should do this again. I said yes I would like that. We both walked towards our cars about five steps and I turned around to look at him and saw that he had turned around and had taken a step back towards me. But then swung right back around kind of nervously and went to his truck. I wish I had walked back to him but I didn't. Instead a called his name. When he responded I said "I had a really great time today" and he said with a big smile in his voice that he did as well.

So now we are on Thursday of this week. On Monday he emailed to say that he had enjoyed seeing me and that he found me very easy to talk with. On Tuesday I emailed to see how his day was going. On Wednesday I felt that I wanted to see him pursuing me a little bit - I didn't email and he didn't email either. So far nothing from him yet today.

I guess I am wondering if he is shy and really needs someone to ask him out or to at least bring up the subject/give him an opening? I believe that I have given him enough from me to know that I will NOT be shooting him down. That I would welcome an invitation. Am I hoping for something from a shy person that perhaps he is not able to do quite yet? Will I be looking desperate/needy/clingy etc if I ask him out again and then see how things are?

Any thoughts would be welcome!
 
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Wiseman2 is online now Wiseman2 Post #2  December 22,2011, 11:33am
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Sounds like the dates went well and your assessment that he is shy is correct. Don't worry about looking "desperate". Just keep being encouraging if things are going well.

Men welcome invitations, particularly from women they like....Good Luck..
_westendgirl_ wrote :
he is shy and really needs someone to ask him out or to at least bring up the subject/give him an opening?

I believe that I have given him enough from me to know that I will NOT be shooting him down. That I would welcome an invitation. Am I hoping for something from a shy person that perhaps he is not able to do quite yet? Will I be looking desperate/needy/clingy etc if I ask him out again and then see how things are?
 
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Ingytravel is online now Ingytravel Post #3  December 22,2011, 11:41am
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That was a lot to take in...lol...but thanks for the details...

I actually see this as a bit of an issue on your end rather than his. From the very start...he made the move and asked if you'd like to go for coffee and you didn't answer him at all...I'm surprised he kept trying!..

So that started his apprehension...As well as you are obviously the one with the busier schedule around your kid/kids...

And then after the first date of meeting for drinks...He, what seems like, attempted to go in for the kiss but as you say, you are the one that overshot the hug...And so once again...you have shown your level of interest to be low. You should have just grabbed his arm at that point to lead him back and kiss him!..

Now it's 3rd date time...and time for YOU to step up and plan and pay for a date. This way, he will know that you are interested...And make sure at the end of the night...if you want to...kiss the man!..

The other part about whether he is enough of an extrovert for you to enjoy his company once actually on the dates...that's going to be up to you.

But from everything you have written...he has tried to show his interest, as well as let you lead on the day because of your schedule, but is unsure about how you are feeling...So go ahead and make that 3rd date and hopefully you will be able to come back and say how great your first kiss was
 
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moonette is offline moonette Post #4  December 22,2011, 1:42pm
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Ingytravel wrote :
That was a lot to take in...lol...but thanks for the details...

I actually see this as a bit of an issue on your end rather than his. From the very start...he made the move and asked if you'd like to go for coffee and you didn't answer him at all...I'm surprised he kept trying!..

So that started his apprehension...As well as you are obviously the one with the busier schedule around your kid/kids...

And then after the first date of meeting for drinks...He, what seems like, attempted to go in for the kiss but as you say, you are the one that overshot the hug...And so once again...you have shown your level of interest to be low. You should have just grabbed his arm at that point to lead him back and kiss him!..

Now it's 3rd date time...and time for YOU to step up and plan and pay for a date. This way, he will know that you are interested...And make sure at the end of the night...if you want to...kiss the man!..

The other part about whether he is enough of an extrovert for you to enjoy his company once actually on the dates...that's going to be up to you.

But from everything you have written...he has tried to show his interest, as well as let you lead on the day because of your schedule, but is unsure about how you are feeling...So go ahead and make that 3rd date and hopefully you will be able to come back and say how great your first kiss was
^^^^ this. The guy could well be unsure that you're interested. You're acting really introverted with him. Tell him you're interested and would like to see him and suggest a date and kiss him.

m
 
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_westendgirl_ is offline _westendgirl_ Post #5  December 22,2011, 3:05pm
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Thanks for the input.

Ingy - I like that he is shy. I think it is a good mix for me because I am someone who sits on the introverted/extroverted fence. I can get on stage and speak to 500 people easily, I enjoy meeting new people one on one but can get shy/flustered at a cocktail party or doing a presentation to a team of my co-workers. I also really enjoy my quiet time and don't need every moment to be filled with chatter. Dating or trying to date someone that is shy is just new to me.

I see what you are saying about him possibly not knowing my interest level. I got into my car and could have kicked myself for not moving my head back so that we could kiss. I was flustered!! So picture two flustered and sheepish grown ups in a parking lot! Beyond silly but kinda of quirky and cute too!

By the way - I DID pay for the second date and basically planned it. He chose the restaurant but it was more about which one in the complex we were closest to.

And you are also right about my schedule. This is something that I wonder about. I don't like getting into my schedule too early on with people. I just let them know the basics. It is not a regular schedule (every other weekend etc). I have a great babysitter and I always make time for a relationship - I just need notice etc when I first start dating someone.

-------------------------------------------------------------------
As an update - He emailed this afternoon after I posted this. He said that it looks like he has Friday afternoon off as his office is closing at noon. I told him that mine was too and would he like to have lunch together before he heads out to finish his Christmas shopping. He said yes but then an hour later said that he would be unable to as his Dad has fallen at the clinic and he would need to work from home tomorrow. He said he would let me know tomorrow how things were going.
Last edited by _westendgirl_; December 22,2011 at 3:51pm. Reason: because i'm wordier than all get-out!
 
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LDJ is offline LDJ Post #6  December 22,2011, 3:49pm
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Plan the next date yourself and make it a day long event if possible, tell him you'd like to plan a day long event and ask him for an available date in January that works for him.

Do you have phone conversations in-between dates, that might work better than the emailing for developing a sustainable connection.
 
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moonette is offline moonette Post #7  December 22,2011, 3:57pm
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Plan something other than a meal. Do something that's a shared interest, and the have a meal or snack/dessert after. I wouldn't wait til January. And since you're interested in the guy, do let him know your schedule.
 
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_westendgirl_ is offline _westendgirl_ Post #8  December 22,2011, 3:59pm
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LDJ wrote :
Plan the next date yourself and make it a day long event if possible, tell him you'd like to plan a day long event and ask him for an available date in January that works for him.

Do you have phone conversations in-between dates, that might work better than the emailing for developing a sustainable connection.
We've only spoken on the phone that one time. It was maybe 30 minutes long. I would like to speak with him on the phone but get a feeling that talking on the phone is comparable to going to the dentist for him. lol.

And NOW it feels weird for me to just pick up the phone and call him. Like I'm changing the game without giving him notice. I think maybe I'll give him a call on Christmas Eve afternoon to wish him a Merry Christmas. And at that time ask him out on a "real" date.
 
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_westendgirl_ is offline _westendgirl_ Post #9  December 22,2011, 4:03pm
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moonette wrote :
Plan something other than a meal. Do something that's a shared interest, and the have a meal or snack/dessert after. I wouldn't wait til January. And since you're interested in the guy, do let him know your schedule.
*nod* We both have some down time between Christmas and New Year's. I was thinking it would be nice to go for a hike. There is a great trail closer to his town that has fire pits etc. I thought I could take a thermos of hot chocolate and a little picnic. Too bad we won't have snow for it - but the weather is still great for a good hike.
 
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moonette is offline moonette Post #10  December 22,2011, 4:06pm
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The hike/picnic sounds nice. I wouldn't wait til Saturday to set it up. I'd email with the plan, but then you have a better idea of what he'd appreciate.
 
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