Phlegm Alley Posted March 9, 2012 Share Posted March 9, 2012 I went on a date with an older woman last night who is much, much older than me. She actually turned out to be older than I initially thought, but I can't remember the last time I've been as physically attracted to a woman, as I am to her. A little background: I met her last Thursday at a Redstone outside of Philly. I was out with co-workers having some post work drinks, when I decided to stick my head into a cougar den. There were a group of 6 older women, still looking very good and seemingly, having a good time. I bought them all a drink. A few of them came over to talk to me and my co-workers and I struck up a conversation with a very attractive woman who, to me, looked like Marisa Tomei. She had a ring on her finger, so I assumed that she was married. While discussing it, she said that she was in fact a widow and she lost her husband five years ago. She asked me what my sign was. I told her I was an Aries to which she responded that her late husband was an Aries as well and that his birthday was April 6th...which happens to be my birthday. This, in addition to the fact that she was very attractive, merited additional conversation. She walked me out to my car that night and we shared an embrace and a kiss and we agreed to go out again the following week. Fast forward to last night. I have been on dates with some very attractive, successful women, but I had never been as nervous as I had been preparing for last night's date. I am 32 years old, and I assumed she was between the ages of 39-43. No big deal. I set up a classy dinner date where we had flights of wine and cheese plates in a wine cellar with a romantic ambiance. Dinner was upstairs an hour and a half later. During dinner, she reveals that she has an 18 year old son heading off to school. She said that she was 29 when she had him, which would make her 47 years old....15 years older than me! Another thing to add is that she is very successful in her own right (she owns her own interior design company), but her late husband was a dental surgeon who lost his life unexpectedly. She has a lot of money, showing up to dinner in a brand new 2012 Mercedes Benz CLS 350, not that it is something that factors in to my attraction to her. Does anyone have any experience or advice? Thanks in advance TSW. Link to comment Share on other sites More sharing options...
ajzepp Posted March 9, 2012 Share Posted March 9, 2012 I'm usually an open book among my TBD brothers and sisters, but in this case I won't go into detail. What I WILL say, however, is that I can wholeheartedly encourage you to pursue this interest, but maintain a "ceiling" on the relationship, so to speak. In other words, date her...even date her exclusively...be honest and up front and enjoy your time together. I just would advise you to not "buy the cow" (sorry, JBoyst). I don't mean that to be disrespectful at all, I think what you've found is fantastic. But the age difference will come into play at some point, so I would enjoy the relationship fully right up to the point where it involves making a long term commitment. But trust me, you're in for a fun ride Link to comment Share on other sites More sharing options...
SWVABillsFan Posted March 9, 2012 Share Posted March 9, 2012 An embrace and a kiss on a 1st night? 15 years older? So when your 50 she is 65, see yourself there? Sounds like you are a boytoy fling. As far as money is concerned, you better look past materila things. If you want the short term older woman experience with a hot cougar, hey, what the heck. You just better look further down the road, what might it be 5 years from now. Link to comment Share on other sites More sharing options...
mead107 Posted March 9, 2012 Share Posted March 9, 2012 47 is the new 30. Go for it. If it is ment to be that you get together then it is ment to be. I find nothing wrong with dating an older women at your age. Just have fun and post pics. Link to comment Share on other sites More sharing options...
Bufcomments Posted March 9, 2012 Share Posted March 9, 2012 To me it sounds like you have some good vibe with her. Good thing about older woman they know what they want and if she is feeling you I say go for it, have some fun and later on down the line if you are still dating find out if it could be a long term thing or just dating. She looks like Tomei and has money too? You lucky dog Link to comment Share on other sites More sharing options...
ajzepp Posted March 9, 2012 Share Posted March 9, 2012 Just have fun and post pics. Link to comment Share on other sites More sharing options...
Mark Vader Posted March 9, 2012 Share Posted March 9, 2012 So she's older than you, so what? Ok, she was a sophomore in high school when you were born, but that's no big deal. If you like her and she likes you and if she's interested in having a real relationship with you, then you treat it as any normal relationship you've had before. Don't let the age difference scare you. Age is just a number. You're both adults so enjoy your time together. Link to comment Share on other sites More sharing options...
Phlegm Alley Posted March 9, 2012 Author Share Posted March 9, 2012 I'm usually an open book among my TBD brothers and sisters, but in this case I won't go into detail. What I WILL say, however, is that I can wholeheartedly encourage you to pursue this interest, but maintain a "ceiling" on the relationship, so to speak. In other words, date her...even date her exclusively...be honest and up front and enjoy your time together. I just would advise you to not "buy the cow" (sorry, JBoyst). I don't mean that to be disrespectful at all, I think what you've found is fantastic. But the age difference will come into play at some point, so I would enjoy the relationship fully right up to the point where it involves making a long term commitment. But trust me, you're in for a fun ride So, you have had some experience with the older women AJ? After a classy date like last night, where we had a great time, what would be an ideal follow up date? Some of the mystique is that I represent something young, exciting, and adventurous from the men that are her age, but should I play that role, or should I assume a more intellectual wine and dine type of posture? Thanks for the response. Link to comment Share on other sites More sharing options...
Doc Posted March 9, 2012 Share Posted March 9, 2012 (edited) Do you want to get married? Do you want kids? Can you see yourself growing old (while she grows older, sorry to be blunt)? As for what she wants, if she's not coming onto you full force and practically begging you to jump her bones, she's probably looking for a relationship. Which gets back to the questions above. Edited March 9, 2012 by Doc Link to comment Share on other sites More sharing options...
mead107 Posted March 9, 2012 Share Posted March 9, 2012 1331322197[/url]' post='2399883']So, you have had some experience with the older women AJ? After a classy date like last night, where we had a great time, what would be an ideal follow up date? Some of the mystique is that I represent something young, exciting, and adventurous from the men that are her age, but should I play that role, or should I assume a more intellectual wine and dine type of posture? Thanks for the response. Take her to a game. Hockey , basketball or a good movie. Link to comment Share on other sites More sharing options...
ajzepp Posted March 9, 2012 Share Posted March 9, 2012 So, you have had some experience with the older women AJ? After a classy date like last night, where we had a great time, what would be an ideal follow up date? Some of the mystique is that I represent something young, exciting, and adventurous from the men that are her age, but should I play that role, or should I assume a more intellectual wine and dine type of posture? Thanks for the response. I do. I got divorced in 2004 and really just have embraced the bachelor lifestyle since that time. I've spent some time with older women and really enjoyed it. I would just be yourself and do things that are consistent with that. IMO, you're at the perfect age for this sort of relationship. You're mature enough that you have a solid feel for who you are, and you're young enough to still be considered "young". I don't know what your long term relationship goals are (not with her, I mean in general), but I'd be careful to always keep your options open just in case that long term potential relationship does happen to come into your life while you're dating this lady. I agree with others, though...if she's looking like Marisa Tomei, you're a lucky dog! And I'm a sucker for Philly girls, so I'm jealous! haha Link to comment Share on other sites More sharing options...
Phlegm Alley Posted March 9, 2012 Author Share Posted March 9, 2012 Do you want to get married? Do you want kids? Can you see yourself growing old (while she grows older, sorry to be blunt)? As for what she wants, if she's not coming onto you full force and practically begging you to jump her bones, she's probably looking for a relationship. Which gets back to the questions above. I just got out of a four and a half year relationship with a woman because we both agreed; we didn't want to get married and we didn't want to have kids. It was amicable, but I believe that life is too short to think about anyone but yourself. I walked her to her car last night and I allowed her to initiate the contact, which she did. We made out like high school kids for 5 minutes, then we said goodbye. One of thefirst questions she asked me when we sat down for dinner was "Have you ever dated an older woman?" I have, but not as old as her. I'm fine with not having kids, getting married, etc. Link to comment Share on other sites More sharing options...
ajzepp Posted March 9, 2012 Share Posted March 9, 2012 I believe that life is too short to think about anyone but yourself. You're the perfect candidate for this type of relationship based on this comment. (seriously) Link to comment Share on other sites More sharing options...
mead107 Posted March 9, 2012 Share Posted March 9, 2012 This could turn into the the best topic this year. Need more details. And pics. Link to comment Share on other sites More sharing options...
Bufcomments Posted March 9, 2012 Share Posted March 9, 2012 not to be cheesy but let us know when u get to second base lol But seriously have your fun and dont let age stop ya. When I was 30 I dated an 40yr old ex-model that lived across the border(Canada) She had money and so did I at the time( was working for GM before they went down the tubes) and we had some nice times with no strings attached. Believe me I had no problems with being her boy toy so to speak. Link to comment Share on other sites More sharing options...
SageAgainstTheMachine Posted March 9, 2012 Share Posted March 9, 2012 So, you have had some experience with the older women AJ? After a classy date like last night, where we had a great time, what would be an ideal follow up date? Some of the mystique is that I represent something young, exciting, and adventurous from the men that are her age, but should I play that role, or should I assume a more intellectual wine and dine type of posture? Thanks for the response. I'm not going to pull a cliche and say "be yourself", because we all wear different masks for different occasions. But at the same time, it's usually best not to intentionally decide upon a persona. I've tried it before, and people can usually tell that you're fabricating something. Link to comment Share on other sites More sharing options...
Guffalo Posted March 9, 2012 Share Posted March 9, 2012 Relax, have fun and just let the relationship run it's natural course. Obsessing about age and differences is counterproductive. If she is attractive and you are getting nervous, feeling butterflies in your stomach before you meet up with her, thats great, those are all good things! Just enjoy your time together, see where it goes. If she was hot and 23 but poor, you probably would not ask for advice, so she is hot, well off and older....big deal, embrace the differences and enjoy! Link to comment Share on other sites More sharing options...
Chef Jim Posted March 9, 2012 Share Posted March 9, 2012 My advice is boink her brains out. I met this great woman in college when I was 19 and she was 26. We dated, fell in love and have been living together for 30 years. Do the math, I'm now 50 she's 57 and that's the perfect age difference in my mind. Had she been the same age difference that you and your date are I'd still be 50 but she'd be 65. Not a thought I want to have. So have fun but don't go the long term route with that age difference. Link to comment Share on other sites More sharing options...
DC Tom Posted March 9, 2012 Share Posted March 9, 2012 I went on a date with an older woman last night who is much, much older than me. She actually turned out to be older than I initially thought, but I can't remember the last time I've been as physically attracted to a woman, as I am to her. A little background: I met her last Thursday at a Redstone outside of Philly. I was out with co-workers having some post work drinks, when I decided to stick my head into a cougar den. There were a group of 6 older women, still looking very good and seemingly, having a good time. I bought them all a drink. A few of them came over to talk to me and my co-workers and I struck up a conversation with a very attractive woman who, to me, looked like Marisa Tomei. She had a ring on her finger, so I assumed that she was married. While discussing it, she said that she was in fact a widow and she lost her husband five years ago. She asked me what my sign was. I told her I was an Aries to which she responded that her late husband was an Aries as well and that his birthday was April 6th...which happens to be my birthday. This, in addition to the fact that she was very attractive, merited additional conversation. She walked me out to my car that night and we shared an embrace and a kiss and we agreed to go out again the following week. Fast forward to last night. I have been on dates with some very attractive, successful women, but I had never been as nervous as I had been preparing for last night's date. I am 32 years old, and I assumed she was between the ages of 39-43. No big deal. I set up a classy dinner date where we had flights of wine and cheese plates in a wine cellar with a romantic ambiance. Dinner was upstairs an hour and a half later. During dinner, she reveals that she has an 18 year old son heading off to school. She said that she was 29 when she had him, which would make her 47 years old....15 years older than me! Another thing to add is that she is very successful in her own right (she owns her own interior design company), but her late husband was a dental surgeon who lost his life unexpectedly. She has a lot of money, showing up to dinner in a brand new 2012 Mercedes Benz CLS 350, not that it is something that factors in to my attraction to her. Does anyone have any experience or advice? Thanks in advance TSW. You're getting ahead of yourself. Go out, have fun, worry about all the baggage later. Older women can be loads of fun. Link to comment Share on other sites More sharing options...
thebug Posted March 9, 2012 Share Posted March 9, 2012 What kind of details would you like Mead? I operate on a policy of full disclosure. As far as pics, her company has a website, with a picture of her posted. Its a bad picture, but a picture none the less. I would start by not posting her name and pic on football website. what happens when "one of the guys" sends her a link to this thread? Link to comment Share on other sites More sharing options...
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