Should I ask him out this time for a 3rd date after almost having sex too soon??

January 29, 2013

So, I've been on two dates with a guy I met online. He's pretty quiet, an introvert maybe, but not shy either. We have a lot of physical chemistry, which I feel is very important, but I want to make sure that's not all we have either. I'd like to go out one more time to see if he breaks out of his shell more. We could also just be incompatible (he's a country boy and I'm a city girl), but for some reason I still want to see where this could go.

Anyway, normally I wouldn't have a problem asking him out this time (he asked me out the last two dates), but on date two we almost had sex. He drove 100 miles both times too see me so this time I told him he could stay with me since it was late and he had a few beers (he wasn't drunk, but still not safe), but joked that a pillow would go between us. He was good and didn't try a thing when we got in bed. He just held me all night and slept. In the morning is when things heated up. He didn't have a condom and I thought it was too soon, but I let him go down on me till I had an orgasm. We were both compeltely naked and I fondled his parts too, but I did not go down on him. He did rub the tip on the outside of me as well, but no penetration. (I probably would have allowed it if he had a condom.) Sorry if this is TMI, but I wanted to point out the details so I could say that I feel like doing all of this is just as bad as sex too soon! Is it?

Now that I'm worried we did too much too soon, I am afraid to be the one to ask him out for a third date. His birthday is on Sunday and I was going to ask him if I could take him out to celebrate on Saturday.

Thoughts?

January 29, 2013

He's probably pissed that he got you off and you didn't reciprocate!

Yes what you did is basically the same as having sex on the 2nd date.

January 29, 2013

Just ask him out . If you guys spent all night together it doesn't sound too soon to me.

January 29, 2013

He asked you out twice and drove 100 miles each time. All you did was lay there and tease him. It's time for you to either move on or arrange a third date.

January 29, 2013

I'd ask him out and be prepared this time

January 29, 2013

AHH!! the "just the tip" game. nice.

January 29, 2013

I'd ask him out and be prepared this time

Yeah, goddammit, it takes two to tango. I think your caution was well-placed.

And I'm sure he would be very reluctant to risk a reckless phukk and the possibility of making you pregnant - when you don't know each other more deeply.....Venture a new date with him - and suggest that, come what may, you both be more ready than last time....

January 29, 2013

Ugh, stomach is in knots right now...I took the plunge and just texted him: "speaking of old age (in a previous text he said he must be getting old because he fell asleep at 9 last night), do you have plans for your bday weekend? If not, I'd love to take you out on Saturday to celebrate. Here or there. Dinner, movie, drinks...whatever floats your boat. :-)"

So upset with myself about Saturday! In my mind, it's complicated everything and now I'm anxious and overanalyzing. I didn't "just lay there and tease him"; he took the initiative and went down on me. It all happened so quickly and it was totally unexpected! If I did have a condom, he would have thought I must have a lot of sex. If I let him have sex without a condom, that would look bad on me (and not to mention risky). If I went down on him, I think I would have looked even sluttier. Besides, as men get older (he's 37; I'm 34), I thought they enjoyed pleasing a woman to orgasm and being unselfish?? If he's upset that he didn't get off, then I don't want a guy like that anyway.

So many grey areas here. Guess I won't know if I messed up until he replies to the text I just sent.

January 29, 2013

Ugh, stomach is in knots right now...I took the plunge and just texted him: "speaking of old age (in a previous text he said he must be getting old because he fell asleep at 9 last night), do you have plans for your bday weekend? If not, I'd love to take you out on Saturday to celebrate. Here or there. Dinner, movie, drinks...whatever floats your boat. :-)"

So upset with myself about Saturday! In my mind, it's complicated everything and now I'm anxious and overanalyzing. I didn't "just lay there and tease him"; he took the initiative and went down on me. It all happened so quickly and it was totally unexpected! If I did have a condom, he would have thought I must have a lot of sex. If I let him have sex without a condom, that would look bad on me (and not to mention risky). If I went down on him, I think I would have looked even sluttier. Besides, as men get older (he's 37; I'm 34), I thought they enjoyed pleasing a woman to orgasm and being unselfish?? If he's upset that he didn't get off, then I don't want a guy like that anyway.

So many grey areas here. Guess I won't know if I messed up until he replies to the text I just sent.

He hasn't replied. It's only been 4 hours, but he always replies almost instantly, even when he's at work. At least he used to...until I nearly put out.

(Grrr...I really hate these double standards! I should be the one judging him for going down on me so soon! Does he do that with every woman on the 2nd date?? Lol)

January 29, 2013

He hasn't replied. It's only been 4 hours, but he always replies almost instantly, even when he's at work. At least he used to...until I nearly put out.

(Grrr...I really hate these double standards! I should be the one judging him for going down on me so soon! Does he do that with every woman on the 2nd date?? Lol)

I'm in a similar predicament and it's causing a lot of stress and confusion for us both.

Ideally sex should wait. It complicates and moves things too quickly, however once it's done or nearly done...those things are done. Then you're left to figure it out later and define the relationship.

January 29, 2013

I'm in a similar predicament and it's causing a lot of stress and confusion for us both.

Ideally sex should wait. It complicates and moves things too quickly, however once it's done or nearly done...those things are done. Then you're left to figure it out later and define the relationship.

I don't even know why I'm stressing over this guy so much! I don't even know if I really even like him...like I said, he's quiet and I wanted to give it one more shot to see if he comes out of his shell. If you recall in a past post of mine, you will see that last week I was irritated about the "somewhere cheap" comment he made in regards to our date. I think it's more of the challenge now in trying to get my dignity back after Saturday and that's why I'm so paranoid! lol

I have never analyzed sex so much until recently, as I came out of an unhealthy relationship as an "OW" and realized I needed to do some work on myself, which included setting some sexual boundaries. I don't think there's a time limit you can really put on it other than when it feels right. My ex-fiance who I was with for 5 years started as a one-night stand. Then after that was over, I had sex with a very good friend one night and we ended up together for a year. Next boyfriend after that was first date sex and that lasted 4 months (not the longest relationship, but sex had nothing to do with us ending it. We were just two different people.) The one I actually decided to wait to have sex with till we were in a committed relationship with, turned out to be the worst of them all because I later discovered he was married! Unfortunately, there's just no simple formula out there regarding when to have sex.

I think now I am the one making sex complicate things by putting too much energy into not making past mistakes, analyzing everything, and contradicting myself, instead of just relaxing and going with the flow.

Maybe I'm just not ready to date.

January 29, 2013

I don't even know why I'm stressing over this guy so much! I don't even know if I really even like him...like I said, he's quiet and I wanted to give it one more shot to see if he comes out of his shell. If you recall in a past post of mine, you will see that last week I was irritated about the "somewhere cheap" comment he made in regards to our date. I think it's more of the challenge now in trying to get my dignity back after Saturday and that's why I'm so paranoid! lol

I have never analyzed sex so much until recently, as I came out of an unhealthy relationship as an "OW" and realized I needed to do some work on myself, which included setting some sexual boundaries. I don't think there's a time limit you can really put on it other than when it feels right. My ex-fiance who I was with for 5 years started as a one-night stand. Then after that was over, I had sex with a very good friend one night and we ended up together for a year. Next boyfriend after that was first date sex and that lasted 4 months (not the longest relationship, but sex had nothing to do with us ending it. We were just two different people.) The one I actually decided to wait to have sex with till we were in a committed relationship with, turned out to be the worst of them all because I later discovered he was married! Unfortunately, there's just no simple formula out there regarding when to have sex.

I think now I am the one making sex complicate things by putting too much energy into not making past mistakes, analyzing everything, and contradicting myself, instead of just relaxing and going with the flow.

Maybe I'm just not ready to date.

I can understand that, sometimes we over think and make ourselves crazy over things that other people haven't even considered. More of a reflection of how we feel about ourselves rather than what they think.

I'm with ya on the not ready to date thing.

January 29, 2013

I was thinking maybe the same thing....

Why not just look at it as a sexy experience?

You were horny.

He was horny.

You met an equal need.

It might progress.

It might not.

Don't stop here.

Keep walking and just enjoy life.

Simply because you have sex with someone doesn't mean they have to turn into a great long loving relationship.

it just means you had a blast.....

Quit over-thinking.

If he replies, great. If not - yeah....... and?

Phukkit.

Move on, and notch it up to experience.

Don't even mark it as a diary entry.

January 29, 2013

I was thinking maybe the same thing....
Why not just look at it as a sexy experience?

You were horny.
He was horny.
You met an equal need.
It might progress.
It might not.

Don't stop here.
Keep walking and just enjoy life.
Simply because you have sex with someone doesn't mean they have to turn into a great long loving relationship.
it just means you had a blast.....

Quit over-thinking.
If he replies, great. If not - yeah....... and?
Phukkit.
Move on, and notch it up to experience.
Don't even mark it as a diary entry.

I like how you think Tara! Even though technically since there was no actual sex, only my orgasm from him heading south, I'm not sure about "equal" needs being met. haha Oh well! I tried to make up for it this weekend, but I guess he just isn't feeling it. Moving on...

January 30, 2013

Oops! So he texted a little over an hour ago and said "Sorry. Still working. But ya. Saturday sounds good to me. :)"

January 30, 2013

After a little pondering the guy probably realized how much of a loser he was and how not worth it the woman was.

I mean for every date he had to drive 200 miles round trip (only a very desperate guy would do something like this!). Also judging from her comment about cheap date, Im pretty sure she still expected him to cover all the expenses during the dates despite the horribly long trip he had to make and the gas expenses he had to spend just to see her. After all these ordeals, the guy probably hoped that at least he could get sex in return. But too bad for him, instead of finally getting something, he ended up only giving again while receiving nothing.

If the guy is smart, he will think this way. But then again, a very desperate man will do anything for a lack of other options.

January 30, 2013

After a little pondering the guy probably realized how much of a loser he was and how not worth it the woman was.

I mean for every date he had to drive 200 miles round trip (only a very desperate guy would do something like this!). Also judging from her comment about cheap date, Im pretty sure she still expected him to cover all the expenses during the dates despite the horribly long trip he had to make and the gas expenses he had to spend just to see her. After all these ordeals, the guy probably hoped that at least he could get sex in return. But too bad for him, instead of finally getting something, he ended up only giving again while receiving nothing.

If the guy is smart, he will think this way. But then again, a very desperate man will do anything for a lack of other options.

He's definitely not desperate, nor am I. We are both very attractive and he got plenty of looks from other women on Saturday when we were out, as did I (from other men). We both have plenty of other options as well. He drove 100 miles each way because he lives on a military base in the middle of no where and I live in the closest city.

And no, I did not expect him to pay for everything. We took turns buying each other drinks. When he got to my house, I offered to drive us around in my car and I did. As I said before, if he "expected" sex then I wouldn't want that type of guy anyway. Should I have had sex without a condom?? No. If he expected something, then why didn't he bring one?

January 30, 2013

So what are you going to do?

January 30, 2013

I am going to take him out and try my best to just be myself and stop analyzing everything!

In the meantime, I've decided not to put all my eggs in one basket this time, and have accepted two dates between now and then! Lol. They are just quick intros with a couple of men I met on match.com. I am meeting one after work tomorrow for a bite to eat and then lunch with another on Thursday.

January 30, 2013

I am going to take him out and try my best to just be myself and stop analyzing everything!

In the meantime, I've decided not to put all my eggs in one basket this time, and have accepted two dates between now and then! Lol. They are just quick intros with a couple of men I met on match.com. I am meeting one after work tomorrow for a bite to eat and then lunch with another on Thursday.

There ya go! Good luck

January 30, 2013

Well glad to hear that he replied and that you're going to have another get together. But be ready to do IT because if you don't that's the end of it based on what you did the other weekend.

January 30, 2013

Well glad to hear that he replied and that you're going to have another get together. But be ready to do IT because if you don't that's the end of it based on what you did the other weekend.

I was planning on it! Good birthday present, right? Lol

January 30, 2013

This thread left me feeling a little queasy. More neurosis than Freud himself could have dealt with.

January 30, 2013

This thread left me feeling a little queasy. More neurosis than Freud himself could have dealt with.

A little harsh, but I can see why you'd feel this way. I've admitted to clearly having issues; perhaps a little psychoanalysis would help.

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Should I ask him out this time for a 3rd date after almost having sex too soon??

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