JC90 Posted June 30, 2011 Posted June 30, 2011 This is very long, but I'd appreciate any input I can get... Met an older woman, went out with her with the mindset of just having fun. The date turns out awesome, we connect both emotionally and physically. She was a great kisser, sexy, sexual, fun, funny, outgoing, all that and all in all the first date was an amazing time. Second time we met up was Saturday. I went out with her and her best girlfriend. We drank, danced, drank, danced, ect.. I kissed and got sexual with both of them on the dance floor and it was, once again, awesome. We go back to her girls place, my clothes start coming off and eventually we all head to the bedroom. Stuff starts getting hot between all three of us, and my original girl initiated it (told me to turn and kiss her friend then come back to her). Unfortunately I had too much to drink and started feeling sick to my stomach so I was unable to "perform." As she drove me back to my car I decided I could either be completely silent and say nothing or take the sensitive, possibly deeper connection building route. I ask her if there's anything she wants to say to me. "To be honest, I'm mortified by the whole situation.." "And by the way, that's not who I am. I'm never the girl to do something crazy like that." We drive back to my car and I tell her I want to talk for a minute. I say, "what happened back there has.. Never happened before and I'm gonna be honest, I don't usually say this to a girl, but I actually kinda like you. I'd like to see you again, but it's up to you." She says "What do you mean it's up to me?" "If I wasn't interested in seeing you again I'd just tell you." I tell her that if she's interested to hit ME up. A little more talk, we make out a few different times in between and one last time before I step out. Couple lovey-dovey texts from her on the way home.. "I like you too, *name* :)" "Hope to see you soon too, looking forward to it :)" Though it all seemed genuine, the straight up "I don't play games, I'd tell you if I weren't interested in seeing you again," the multiple short, passionate make outs before I left that she initiated, the lovey-dovey texts, I'm not totally sure that she wasn't just doing all of it because she understood that my pride was crushed and that I was extremely embarrassed so she just wanted to make me feel better. Also got a text from her a day later asking "did anything about last night bother you? (besides feeling ill of course) Just curious :)" I responded, "I had a lot of fun with you all. Nothing really bothered me (except being sick obviously), but to be honest I rather it have been just you and me in the other room at the end of the night." To which she responded saying something like "Aww, I'm flattered, you're a very sweet person *name* :)" Then I went on to tell her how we obviously have an emotional and physical connection so I don't feel the need to play any games. She says she's glad I don't, because neither does she. She's leaving Thursday to go out of town for a week (work), but I texted her Monday night anyways. "We should go out before you leave for your trip." *2 hours later* "Sorry for the delay, at work blah blah. I don't know how to make that happen, this week before I leave is nuts..." "Tomorrow night, just you and me, wear something flirty, downtown annapolis, a little breaking benjamin in the car and we see where the night takes us." "That sounds shockingly like a come on :D" "Maybe just a little bit ;)" "You don't need me to get laid cutie ;)" "That's flattering, but I'm not taking you out just to get laid." "I'm skeptical :D" "Still huh? If all I wanted from you was sex I probably wouldn't still be pursuing you. So are you down for tomorrow night or scared you might actually have fun three times in a row with the same guy? :D" "Lemme see what I can do, but I can't make any promises because I have a ton of work to finish before I go :)" "Gotcha. Hit me up tomorrow." Was a little weirded out by the whole her acting like she thinks I'm JUST trying to have sex with her, didn't expect or understand that.. Then got this text from her at 3:30 AM: "Gah.. Awake. Urg" When I woke up I sent her "Hey, Miss Insomniac, just got your text.. Manage to get any sleep?" No response from her all Tuesday. At first I figured she was just sleeping, but then it was seemed like I was being ignored. Not very hard to send a text saying yes or no, even if you're super busy. I feel like I'm getting crazy mixed signals from her.. From her asking me if anything about our night out bothered me to her ignoring me. Going to wait and text her next Thursday or Friday when she should be back from her trip and see what happens. Input? Opinions?
spiderowl Posted June 30, 2011 Posted June 30, 2011 Don't know. It's a bit confusing because she initiated the thing with the other woman, if you are telling the story right, and yet she's saying that's not her? She seems wary of seeing you again. Maybe she wasn't actually happy with your behaviour but I can't see why she would complain if it was her idea. It is strange. Final thought is that older women (myself included) get quite a few approaches from younger guys who are basically doing just what you did and looking for a bit of fun. Although we enjoy fun too, we are not just looking for sex on a few occasions until he meets a younger woman - in other words, we are not there to be his sex doll until he meets the real thing. I don't think younger guys realise this as they assume an older woman wants the same as they do, just a bit of fun. Then, they get attached to us and start to want a relationship. Talk about confusing! She probably doesn't trust you to know what you want and doesn't want to be used. You need to think carefully about your own motives. Are you really looking for a possible long-term relationship with this woman or just peeved that she isn't immediately jumping on you gratefully because you're young and attractive? For a mature woman, young and attractive isn't enough.
Imajerk17 Posted June 30, 2011 Posted June 30, 2011 (edited) (1) How old are you both, and how did you meet this woman? (2) In relation to (1), I am actually pretty familiar with the town you mentioned. Interesting culture. My short answer would be to actually give her a call. EDIT: I'm not sure you needed to mention explicitly the "breaking benjamin" . You might have gotten her "anti-slut defenses" up with that. Think about it: She had sex with you twice and as she doesn't know you that well, on some level she is wondering whether it really was a good idea. Now it sounds that you are expecting sex every time you meet. Subtlety would have been your friend here. Edited June 30, 2011 by Imajerk17
Author JC90 Posted June 30, 2011 Author Posted June 30, 2011 (1) How old are you both, and how did you meet this woman? (2) In relation to (1), I am actually pretty familiar with the town you mentioned. My short answer would be to actually give her a call. I'm 21 and she's 40. We met on a dating site then had a drink for our first date. I've gotten some previous advice saying all she wanted from me all along was sex and me getting emotional is a turn-off for her. But at the same time she didn't want to have sex on the first date (we got sexual, but no sex) and as I remember she brought up the subject of why I was going out with an older woman multiple times. She kept saying things like "do you think an older woman is just going to be easier to get in bed/an easy lay? Because that's not going to happen/not me." To which I reassured her over and over that I wasn't just looking for a quick and easy lay, and that I was out with her because age is just a number to me and I go out with women that I'm attracted to.
spiderowl Posted June 30, 2011 Posted June 30, 2011 (edited) ^^^ Completely agree with Imajerk. Breaking Benjamin is just puerile slang and implies you think of her as a slut. Also, calling her 'cutie' is a bit damning and again puts her into the cateogry of casual booty call. I think you shot yourself in the foot here and she saw that, despite what you said, your interest is superficial and focused on sex. Believe me, that "age is just a number" line is so well worn. She was trying to find out what motivated you and wasn't convinced you weren't yet another shallow booty call hunter. Edited June 30, 2011 by spiderowl
Imajerk17 Posted June 30, 2011 Posted June 30, 2011 (edited) I'm 21 and she's 40. We met on a dating site then had a drink for our first date. I've gotten some previous advice saying all she wanted from me all along was sex and me getting emotional is a turn-off for her. But at the same time she didn't want to have sex on the first date (we got sexual, but no sex) and as I remember she brought up the subject of why I was going out with an older woman multiple times. She kept saying things like "do you think an older woman is just going to be easier to get in bed/an easy lay? Because that's not going to happen/not me." To which I reassured her over and over that I wasn't just looking for a quick and easy lay, and that I was out with her because age is just a number to me and I go out with women that I'm attracted to. Read my edit, even in light of what you said here, I still think it stands. Every guy says a version of what you said dude. C'mon. Not classy. And if all she wants is sex and doesn't want to get emotional with you, meeting up a third time isn't a good idea. She knows that and is stonewalling on the date. Also, she just might not view you as relationship material anyway. You have to realize that 21 is young. She has a lot of life experience that you presumably do not have yet. You've been an adult for a few years, she has been an adult practically your whole life. Now before you cut in with "but I'm much wiser than my years": You're showing your age/place in life/maturity level by how you handled this situation. Not to knock you or anything because now is the time in your life to be getting experience and learning. A seasoned man in his 30's would have known better than to make the "mistakes" you made though. What did you and she actually talk about on the date? Edited June 30, 2011 by Imajerk17
Author JC90 Posted June 30, 2011 Author Posted June 30, 2011 ^^^ Completely agree with Imajerk. Breaking Benjamin is just puerile slang and implies you think of her as a slut. Also, calling her 'cutie' is a bit damning and again puts her into the cateogry of casual booty call. I think you shot yourself in the foot here and she saw that, despite what you said, your interest is superficial and focused on sex. Believe me, that "age is just a number" line is so well worn. She was trying to find out what motivated you and wasn't convinced you weren't yet another shallow booty call hunter. Whoa, whoa, whoa.. You all must have not read everything correctly here. The Breaking Benjamin comment I didn't think needed explaining (and that's an odd assumption to make about the band). I said that in my text because we had talked about how we both like that band on Saturday night. I would never usually admit this, but I was trying to cater to her taste in music.. Next, I didn't call her cutie, that's what she called me in the text.. You must have read it wrong.. ME: "We should go out before you leave for your trip." *2 hours later* HER: "Sorry for the delay, at work blah blah. I don't know how to make that happen, this week before I leave is nuts..." ME: "Tomorrow night, just you and me, wear something flirty, downtown annapolis, a little breaking benjamin in the car and we see where the night takes us." HER: "That sounds shockingly like a come on :D" ME: "Maybe just a little bit ;)" HER: "You don't need me to get laid, cutie ;)" ME: "That's flattering, but I'm not taking you out just to get laid." HER: "I'm skeptical :D" ME: "Still huh? If all I wanted from you was sex I probably wouldn't still be pursuing you. So are you down for tomorrow night or scared you might actually have fun three times in a row with the same guy? :D" HER: "Lemme see what I can do, but I can't make any promises because I have a ton of work to finish before I go :)" ME: "Gotcha. Hit me up tomorrow." Then got this text from HER at 3:30 AM: "Gah.. Awake. Urg" When I woke up I sent her "Hey, Miss Insomniac, just got your text.. Manage to get any sleep?" Lastly, we haven't had sex. We've GONE OUT twice. The first time there was no sex, just mutual kissing and touching. The second time was what I mentioned in my OP, I was drunk and got sick, so it (sex) didn't happen. And on the date we talked about all different stuff..
Imajerk17 Posted June 30, 2011 Posted June 30, 2011 OK, cool about the breaking benjamin part! Still, 21 and 40 might be too much of an age difference in her mind. And as she might not be looking for a relationship, seeing you 3 times might not be in her mind, a good idea.
Author JC90 Posted June 30, 2011 Author Posted June 30, 2011 OK, cool about the breaking benjamin part! Still, 21 and 40 might be too much of an age difference in her mind. And as she might not be looking for a relationship, seeing you 3 times might not be in her mind, a good idea. Unfortunately you might be right ..I have other options but it's such a shame that the girls I have actually liked and connected with have all ended up rejecting me... I guess I'm just a fool for believing she was unlike the other girls and would tell me she wasn't interested (like she said) instead of leading me on. I guess the only way to find out for sure is to wait till she gets back next week and shoot her one more text and see what happens. My gut feeling isn't so good..
Cee Posted June 30, 2011 Posted June 30, 2011 I'm 41 woman and in a LTR with a 24 year old so older women/younger men can work. I think you have an uphill battle because of the two of you getting sexual too fast. And the threesome thing would derail almost any dating situation. So she might be so embarrassed, she wants to drop the whole thing. Also, I think you are coming on too strong. If you want a relationship, ask her on proper dates using the telephone (and not text). There's no rush to see her. Simply schedule a time and an interesting itinerary. Try to keep alcohol at a minimum and leave plenty of time for discussion. See if you are truly compatible with her and let things progress. Another thing to consider is are you really mature enough to date an older woman? You might be, but I'm asking. Also is she immature enough to date a younger man? My boyfriend can deal with stuff like taking me to get a biopsy for cancer. And I can deal with him doing a beer bong at a party and gaming on PS3 for hours at a time. The both of you must mix maturity, common sense, and fun. Sometimes that balance is hard to achieve. P.S. I missed the entire Breaking Benjamin reference so she may have as well. I had one of their albums so when I read your text, I naively thought you were talking music. Now I feel old.
Author JC90 Posted June 30, 2011 Author Posted June 30, 2011 I'm 41 woman and in a LTR with a 24 year old so older women/younger men can work. I think you have an uphill battle because of the two of you getting sexual too fast. And the threesome thing would derail almost any dating situation. So she might be so embarrassed, she wants to drop the whole thing. Also, I think you are coming on too strong. If you want a relationship, ask her on proper dates using the telephone (and not text). There's no rush to see her. Simply schedule a time and an interesting itinerary. Try to keep alcohol at a minimum and leave plenty of time for discussion. See if you are truly compatible with her and let things progress. Another thing to consider is are you really mature enough to date an older woman? You might be, but I'm asking. Also is she immature enough to date a younger man? My boyfriend can deal with stuff like taking me to get a biopsy for cancer. And I can deal with him doing a beer bong at a party and gaming on PS3 for hours at a time. The both of you must mix maturity, common sense, and fun. Sometimes that balance is hard to achieve. P.S. I missed the entire Breaking Benjamin reference so she may have as well. I had one of their albums so when I read your text, I naively thought you were talking music. Now I feel old. Man.. Everyone's opinion is different... Some think she just wanted sex with a boy toy the whole time and me being unable to perform that night then bringing up feelings killed all her interest, some think she's interested but just needs some time, some think she's interested but super busy, some think she's interested in more than just sex but thinks all I want is sex so she's distant, you say she might just be embarrassed and possibly wants to drop our "relationship" altogether. I should've known I'd get all these different opinions, but holy crap.. I'm just more confused then ever now!
Cee Posted June 30, 2011 Posted June 30, 2011 Hahaha, we are just individual people with our opinions. I have no idea what she wants. Your best bet is to read her signals of interest/disinterest when she returns from her trip. From what you've written, I think she is keeping you at arms length. I think she needs a little time to decide what to make of you. And remember, it's not like you had a normal second date. It sounded more like a drunken hookup to me. This sounds more like a set up for a FWB than an LTR. But who knows?
spiderowl Posted July 1, 2011 Posted July 1, 2011 OK, sorry, I misunderstood and an apology is in order. What you said sounds a lot better now you interpreted it. Maybe she just isn't feeling that emotional connection that she needs? I'm older than her but I did go out with a guy 20 years younger than me because he seemed so keen and he sounded like a nice guy. When we met, however, he really seemed too young. His language was young and hip and he was too informal, talking to me as if I was a young best mate or something. I felt as if I should see him home safely! Yet, this was an intelligent guy, nice looking and with good manners. If he had been 15 years older, I would have been seriously interested, but I knew that he was a different generation brought up with different language and customs. I knew he had a lot of learning to do before he had my life experience. I also thought that despite him seeming genuine, he was probably not looking further ahead than bed at the time and after he'd satisfied his curiosity about older women would move on to a woman of his own age and settle down to have a family. So, I had to leave him at the date really. It's very sad but one has to be realistic.
Author JC90 Posted July 2, 2011 Author Posted July 2, 2011 This is pretty embarrassing, but I told one of my best friends the whole story, showed him the girl, and he ended up making a profile on the dating site I met her on and sending her a message (I WAS NOT told about this "plan" until after I saw what he had done). He put a pic of a random good looking guy as his pic, put the age to 27, filled out a couple things in the profile, then sent her a message. Oddly enough, she responded, they bantered back and forth some, then when he got her to the point where she wanted to meet up he sent her this: "Before we meet I'm kinda curious of something though.. I've dated some more "mature" women, and whenever I think of a younger man/older woman relationship now, what comes into my mind is that the woman is looking for a boy toy, a party boy, and/or a younger guy to fulfill some kind of sexual fantasy. If I'm totally wrong please tell me! I just want to know *exactly* what you're looking for so I have an idea of what to expect (or what not to expect)." Then she sent him this: "Heh. I don't need or want a 'boy toy'. Frankly age isn't something I spend a lot of time thinking about lol, you're gonna have a hard time keeping up with me *name* I don't Fu** around. Never have. So you don't need to worry about my motivation. I just like to be with chill people, I work with douchebags on Capital Hill. I'm looking to hang out *name*. I don't need someone to 'complete me' . There is something I want. Require. Honesty. I'm not interested in your life story, you are a stranger to me, and honestly I approve of your scantly filled-in profile. I do, however, want to know your real age." Sounds to me like she's trying to hide the fact/saying without trying to look like a slut that she wants no strings attached sex with younger guys. Or am I wrong?
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