In need of a lady's perspective: I am 25, she is 38

[jjbot]

I'm curious to get a woman's (preferably older) read on the situation that I'm in.

 

To give you some background:

- I am 25 and she is 38 (not married).

- We work at the same company on the same floor in somewhat close proximity of one another

- She is usually very reserved and passive

 

To be completely honest, I am certain I have feelings for this lady or else I wouldn't be on here writing this post now. However, with the large age difference and the fact that we work at the same company, I do have some apprehension towards taking things forward. However, I am rather curious to hear some thoughts as I try to gauge what she thinks of me.

 

At the beginning of the year, we were merely colleagues and our communication was strictly as such. But as we exchanged emails more frequently, we started to build a nice rapport and several months ago, I finally built the courage to ask her to lunch. Since then, we have been to lunch together several times and have gone out to get drinks after work a few times.

 

As I mentioned earlier, she is usually very passive to other people and her tone in the emails she writes me is completely different from what I have seen in her emails to others. For instance, she will write things like "hope you have a nice weekend!" or "take care!". She will also include smileys like :-) or :-P . While this would be completely normal for some people, it just seems so out of character for her.

 

While this all sounds nice and peachy, I sometimes get the feeling that I am pushing too hard and that I am actually annoying her / making her feel uncomfortable. Although signs point to at least some sort of interest at the surface, all communication has been initiated from my end. While she has never turned me down when I ask her to lunch or to grab dinner and drinks, it has always been me to start the conversation, etc.

 

The questions echoing in my mind are....

 

- Am I coming on too strong by ALWAYS initiating the conversation and asking her to lunch/drinks, etc?

- Does she find my persistence annoying?

- And is she just being nice when she goes to lunch/dinner/drinks with me and writing me friendly emails?

 

Perhaps I am just lacking confidence and just over-thinking the situation, but I'm really not sure what to think especially given that I have never dated an older woman and this lady is 14 years older than me.

 

Apologies for the long post, but if someone would like to share their thoughts, I would love to get some perspective.

 

P.S. we are going out to get drinks next Friday (with one another female colleague)

[Disenchantedly Yours]

25 and 38 is a big age gap. You might be in different places in your life but you don't need me to tell you that. You sound serious about her and not like your using her so I think that's good.

 

As for your questions:

 

- Am I coming on too strong by ALWAYS initiating the conversation and asking her to lunch/drinks, etc?

 

It doesn't sound like you are coming on too strong at all. After all, you did build up a repitore with her for a few months before that. I personally like a man that intiates and asks me out instead of being more passive. If you understand she is passive, then my guess is she likes it too that you ask her.

 

 

- Does she find my persistence annoying?

She doesn't appear to. Does she usually say "yes" when you ask her for lunch or drinks

 

- And is she just being nice when she goes to lunch/dinner/drinks with me and writing me friendly emails?

 

She wouldn't go if she didn't like you. Whether that interest is romantic is hard to tell. It's hard to tell where she stands from the information you gave. She could write friendly emails to other co-workers that you don't see.

 

Why don't you ask her to lunch or drinks one day with just the two of you, ask her if she is seeing anyone. Causual questions like that and go from there.

[Pierre]

At age 38 she is on the downside whereas you are on the up.

 

Are you 100% certain she is not in a relationship?

[jjbot]

25 and 38 is a big age gap. You might be in different places in your life but you don't need me to tell you that. You sound serious about her and not like your using her so I think that's good.

 

As for your questions:

 

- Am I coming on too strong by ALWAYS initiating the conversation and asking her to lunch/drinks, etc?

 

It doesn't sound like you are coming on too strong at all. After all, you did build up a repitore with her for a few months before that. I personally like a man that intiates and asks me out instead of being more passive. If you understand she is passive, then my guess is she likes it too that you ask her.

 

 

 

She doesn't appear to. Does she usually say "yes" when you ask her for lunch or drinks

 

 

 

She wouldn't go if she didn't like you. Whether that interest is romantic is hard to tell. It's hard to tell where she stands from the information you gave. She could write friendly emails to other co-workers that you don't see.

 

Why don't you ask her to lunch or drinks one day with just the two of you, ask her if she is seeing anyone. Causual questions like that and go from there.

 

While I completely understand (or pretend to) the significant age gap and that we are likely at different stages of the journey we call life, its just really hard to ignore my feelings. With that being said however, I honestly do not know where I want this to end up.

 

In the short term, my feelings desire a deeper relationship. But realistically, given that the prospect for a successful long term relationship with someone 14 years older than me is near impossible, I have some reservations on taking things forward.

 

But thank you for your suggestion. I think I will bring up the topic of dating when we go out next time. Since we are both pretty close to the other colleague we are going out with next Friday, I think it may provide a nice forum to have a casual discussion on dating to see where she stands.

 

Since I am a complete worrybug and I worry about things I have absolutely no reason to worry about, the point I wanted to confirm most was that she would not go to lunch/dinner/drinks with me if she found me to be annoying and of zero interest, correct? She has always been very open and receptive to my invitations...

[jjbot]

At age 38 she is on the downside whereas you are on the up.

 

Are you 100% certain she is not in a relationship?

 

I am not 100% certain she is not in a relationship. And I completely agree that the age difference is serious consideration. I don't really know where I want this end up. I just know where I don't want this to end up and that is her thinking I am some creepy, obsessive boy who always asks her to lunch and get drinks, etc. lol

[xxoo]

I am not 100% certain she is not in a relationship. And I completely agree that the age difference is serious consideration. I don't really know where I want this end up. I just know where I don't want this to end up and that is her thinking I am some creepy, obsessive boy who always asks her to lunch and get drinks, etc. lol

 

If she continues to say yes, it doesn't sound like she is annoyed or creeped out. "Yes" is positive reinforcement. She's old enough turn down an invitation she doesn't want (or should be).

 

At 25/38, you are both near your sexual peak. This could be a very fun short term relationship! I'm close to her age, and would not consider a serious relationship with a 25 year old. The work dynamic is another consideration altogether...

 

Another possibility is that she just enjoys your attention, and wants nothing more.

[leftfordead2]

does she have kids?

[FitChick]

I don't think the age gap is as much of a problem as the fact that you work together. That is a dealbreaker for me. I've done it and would never do it again. It's like dating a famous person -- everyone wants to know what you're up to.

 

I prefer dating younger men but the perceived "age gap" is larger when you are younger. A man in his 40s dating a woman in her 50s is "closer in age" than someone in their 20s/30s, in my opinion. Has to do with life experience.

[KathyM]

I'm curious to get a woman's (preferably older) read on the situation that I'm in.

 

To give you some background:

- I am 25 and she is 38 (not married).

- We work at the same company on the same floor in somewhat close proximity of one another

- She is usually very reserved and passive

 

To be completely honest, I am certain I have feelings for this lady or else I wouldn't be on here writing this post now. However, with the large age difference and the fact that we work at the same company, I do have some apprehension towards taking things forward. However, I am rather curious to hear some thoughts as I try to gauge what she thinks of me.

 

At the beginning of the year, we were merely colleagues and our communication was strictly as such. But as we exchanged emails more frequently, we started to build a nice rapport and several months ago, I finally built the courage to ask her to lunch. Since then, we have been to lunch together several times and have gone out to get drinks after work a few times.

 

As I mentioned earlier, she is usually very passive to other people and her tone in the emails she writes me is completely different from what I have seen in her emails to others. For instance, she will write things like "hope you have a nice weekend!" or "take care!". She will also include smileys like :-) or :-P . While this would be completely normal for some people, it just seems so out of character for her.

 

While this all sounds nice and peachy, I sometimes get the feeling that I am pushing too hard and that I am actually annoying her / making her feel uncomfortable. Although signs point to at least some sort of interest at the surface, all communication has been initiated from my end. While she has never turned me down when I ask her to lunch or to grab dinner and drinks, it has always been me to start the conversation, etc.

 

The questions echoing in my mind are....

 

- Am I coming on too strong by ALWAYS initiating the conversation and asking her to lunch/drinks, etc?

- Does she find my persistence annoying?

- And is she just being nice when she goes to lunch/dinner/drinks with me and writing me friendly emails?

 

Perhaps I am just lacking confidence and just over-thinking the situation, but I'm really not sure what to think especially given that I have never dated an older woman and this lady is 14 years older than me.

 

Apologies for the long post, but if someone would like to share their thoughts, I would love to get some perspective.

 

P.S. we are going out to get drinks next Friday (with one another female colleague)

As an "older woman", I'll give you what I think is her perspective. She enjoys your company. She enjoys the attention she is getting from you. She maybe thinks you're cute, attractive, interesting, or whatever. She may even consider having a fling with you, but as far as a long lasting relationship, she's probably not interested in you in that way. Most women would consider you too young to develop a lasting relationship with, and she'd probably dump you for someone closer to her own age as soon as that someone came along. I suggest you stick to women closer to your own age. I don't see this relationship progressing past a certain level.

[Ruby Slippers]

Just go for it. If it's too much, she'll make that clear.

 

I am 35 and have a 26-year-old lover. One of the things I like most about him is that he's assertive and very clear about what he wants. If he were to come on too strong, I would let him know. But so far, that hasn't been the case.

[Professor X]

Just go for it. If it's too much, she'll make that clear.

 

I am 35 and have a 26-year-old lover. One of the things I like most about him is that he's assertive and very clear about what he wants. If he were to come on too strong, I would let him know. But so far, that hasn't been the case.

 

Haha, no wonder your sex is so great.

You're both in your prime

[Cee]

Listen to your heart. If you like her, take a chance.

 

We tend to make up all sorts of reasons why someone might not like us (e.g., just got out of a relationship, different culture, etc.). It's a normal defense mechanism, but to truly live your life you must take a risk.

 

I have always flouted the conventions of courtship because they are based in fear and false appearances. To succeed in life (and romance), you must be independent and fearless.

 

Be fearless and see what happens next.

[sweetypielovely]

I am 40 and my BF is 29. We get along fine. I have no issues with the age difference.

 

I dont think she sees you as a pest. If she did im sure she would reject your invites right up front. I think she knows you like her and she seems to like you.

[bac]

The situation depends on personal preferences. Some older women love younger guys. I am a woman. I love younger guys so I would be happy to have sex with you. A woman of 38 who loves younger guy might try to have a R with you. Also, there are women who do not like younger guys at all so she will reject you if she is one of them. Also, there are women who are not sure about the issue. They feel sexual attaction to younger guys but they are very afraid of the outcomes and they do not want to take risks.

As for risks, she is going to fall for you very badly, but you are going to want younger girls after some period of time.

[April72]

No offense here.... but I am a 39 yr old female.... and though the attention of a 25 yr old male would be flattering.... I would consider you a baby and wouldn't want the hassle of dealing with the maturity level of a 25 yr old. Been there done that... it's exhausting. I'm sure your a great guy... it's nothing against you personally just your age range. Now I'm sure a ONS kinda deal might be fun... but I wouldn't take you serious for anymore then a friend. But that is just me.

 

There are lots of cougars these days that perfer men much younger. So I say go for it you have nothing to lose. And if she says she wants to stay friends... then you still have a good friend.

 

another thing I never fish out of the company pond. Learned that lesson the hard way as well.

[Ruby Slippers]

Haha, no wonder your sex is so great.

You're both in your prime

I know. He brings it, I bring it, and that brings an inferno of hotness.

[SierraRose]

My advice as a 41 year old woman? You are going to be a toy and a pump for her ego. Don't **** where you eat...

[jjbot]

Thanks all for the thoughtful remarks! It is very helpful to get the input of others. As reflected in many of your responses, the prospect of a relationship may be difficult given the age difference and the fact that we work together.

 

As one of you suggested, I am pretty sure she knows I like her given all of my advances. Perhaps she does like the attention of someone a lot younger than her. Or perhaps she just sees me as a cute little boy and enjoys a fresh companion from time to time.

 

For the time being, I absolutely enjoy her company and hopefully she enjoys mine (albeit on a different level perhaps). I definitely do not want a situation that makes things weird at the office so maybe it is to leave things as they are without making a definitive push.

 

I also think that going out with a much older woman can teach me a lot about the opposite gender (which is always beneficial lol).

 

Just to add some more background, I live in Japan so this is taking place across the pacific from most of you where the culture is somewhat different. I am Japanese American (speak both English and Japanese) while she is purely Japanese. I think that is another harbinger of interest on her end...

[Disenchantedly Yours]

But thank you for your suggestion. I think I will bring up the topic of dating when we go out next time. Since we are both pretty close to the other colleague we are going out with next Friday, I think it may provide a nice forum to have a casual discussion on dating to see where she stands.

 

Awesome idea. It's always fun to talk about dating or just general issues men and women face with each other in mixed company.

 

Since I am a complete worrybug and I worry about things I have absolutely no reason to worry about, the point I wanted to confirm most was that she would not go to lunch/dinner/drinks with me if she found me to be annoying and of zero interest, correct? She has always been very open and receptive to my invitations...

 

Yes. She would not go to lunch/drinks with you if she found you annoying and had no interest in you or your companionship. What kind of companionships she is looking for might be tougher to figure out.

 

The age gap is difficult but it doesn't make it impossible. Young women date men 14 years older then them plenty. You don't have to have it all figured out what you want out of your relationship with this woman but be mindful of always treating her with respect regardless. Lets us know what happens.

[jjbot]

Just to give you an update...

 

I've been staying close with her since the last time I posted about 6 months ago. Nothing has really developed too far beyond where I left it last time (nothing has really cooled off either...) Again, I over analyze everything way too much but had some thoughts I wanted to share.

 

- We went out for dinner and drinks with another single, unmarried colleague (with whom she is very close with) last Friday and at about 10:30pm this colleague says that she has to go home. Before going home she kept pushing us to stay and have another drink with just the two of us. The way she kept suggesting us numerous times to stay back and grab another drink after she leaves was quite strange and almost forced....just made me think whether she knew something and was trying to tee something up for us?

 

- Anyway we walked the colleague to the train station said goodbye to her and now we were just the two of us and we went to find another place to have a drink. We went to like 4-5 stores but they were all closing so we couldn't get in. We concluded that it wasn't meant to be that night and we called it a night. Since then I did invite her to get together for dinner/drinks with just the two of us next week. Unfortunately the week after next is a big holiday in Japan so things are very hectic until the holiday passes and so she responded "unfortunately I can't make it next week. so maybe after the holiday? lets arrange for after the holiday"

 

Just trying to get a read on the situation and whether she's interested or not

[RedRobin]

Just to give you an update...

 

I've been staying close with her since the last time I posted about 6 months ago. Nothing has really developed too far beyond where I left it last time (nothing has really cooled off either...) Again, I over analyze everything way too much but had some thoughts I wanted to share.

 

- We went out for dinner and drinks with another single, unmarried colleague (with whom she is very close with) last Friday and at about 10:30pm this colleague says that she has to go home. Before going home she kept pushing us to stay and have another drink with just the two of us. The way she kept suggesting us numerous times to stay back and grab another drink after she leaves was quite strange and almost forced....just made me think whether she knew something and was trying to tee something up for us?

 

- Anyway we walked the colleague to the train station said goodbye to her and now we were just the two of us and we went to find another place to have a drink. We went to like 4-5 stores but they were all closing so we couldn't get in. We concluded that it wasn't meant to be that night and we called it a night. Since then I did invite her to get together for dinner/drinks with just the two of us next week. Unfortunately the week after next is a big holiday in Japan so things are very hectic until the holiday passes and so she responded "unfortunately I can't make it next week. so maybe after the holiday? lets arrange for after the holiday"

 

Just trying to get a read on the situation and whether she's interested or not

 

As a woman who has been pursued many times by the young'ins... I'd say she is interested.

 

I'd also say she isn't interested in a fling.

 

I've turned away younger men for lots of reasons. It would take a very special fella for me to consider becoming involved with one. I'm not interested in helping a younger man get his 'learn on'... and I also am not up for a fling. Large age gap relationships are often unbalanced (but not always). She doesn't sound predatory at all... which is another 'red flag' to me. When the older chases the younger, it kind of looks and feels rather 'off' to me and not healthy. But that is just me.

 

Considering the fact that you work together, I'd say the go slow approach you are doing works just fine.

 

Make sure you do not enter anything sexual without good communication up front, is my suggestion.

[Radu]

I also think that going out with a much older woman can teach me a lot about the opposite gender (which is always beneficial lol).

 

Just to add some more background, I live in Japan so this is taking place across the pacific from most of you where the culture is somewhat different. I am Japanese American (speak both English and Japanese) while she is purely Japanese. I think that is another harbinger of interest on her end...

 

Ya think ???

Really, in Japan being Japanese American could be considered very interesting by women ... no way !

Yes, i'm being sarcastic ... they are very interested in that.

 

One piece of advice ... do not date coworkers. In Japan from what i know women generally are very quiet about who they date, but it can still become a problem.

[manup]

I'm curious to get a woman's (preferably older) read on the situation that I'm in.

 

To give you some background:

- I am 25 and she is 38 (not married).

- We work at the same company on the same floor in somewhat close proximity of one another

- She is usually very reserved and passive

 

To be completely honest, I am certain I have feelings for this lady or else I wouldn't be on here writing this post now. However, with the large age difference and the fact that we work at the same company, I do have some apprehension towards taking things forward. However, I am rather curious to hear some thoughts as I try to gauge what she thinks of me.

 

At the beginning of the year, we were merely colleagues and our communication was strictly as such. But as we exchanged emails more frequently, we started to build a nice rapport and several months ago, I finally built the courage to ask her to lunch. Since then, we have been to lunch together several times and have gone out to get drinks after work a few times.

 

As I mentioned earlier, she is usually very passive to other people and her tone in the emails she writes me is completely different from what I have seen in her emails to others. For instance, she will write things like "hope you have a nice weekend!" or "take care!". She will also include smileys like :-) or :-P . While this would be completely normal for some people, it just seems so out of character for her.

 

While this all sounds nice and peachy, I sometimes get the feeling that I am pushing too hard and that I am actually annoying her / making her feel uncomfortable. Although signs point to at least some sort of interest at the surface, all communication has been initiated from my end. While she has never turned me down when I ask her to lunch or to grab dinner and drinks, it has always been me to start the conversation, etc.

 

The questions echoing in my mind are....

 

- Am I coming on too strong by ALWAYS initiating the conversation and asking her to lunch/drinks, etc?

- Does she find my persistence annoying?

- And is she just being nice when she goes to lunch/dinner/drinks with me and writing me friendly emails?

 

Perhaps I am just lacking confidence and just over-thinking the situation, but I'm really not sure what to think especially given that I have never dated an older woman and this lady is 14 years older than me.

 

Apologies for the long post, but if someone would like to share their thoughts, I would love to get some perspective.

 

P.S. we are going out to get drinks next Friday (with one another female colleague)

 

Try and bang her, do not try and start a weird relationship.

[bac]

 

- Am I coming on too strong by ALWAYS initiating the conversation and asking her to lunch/drinks, etc?

- Does she find my persistence annoying?

- And is she just being nice when she goes to lunch/dinner/drinks with me and writing me friendly emails?

 

 

- You should initiate everything because you are a man

- I think you should figure out what she thinks by yourself.

She definitely wants you.

IMO, she is probably fine with your persistence but she wants much more (sex).

She will behave according to her core beliefs. If she believes that dating younger guys is not a good idea, she will reject any young guy. If she believes that it is great, she will accept you.

How can people from LS know her intentions? Make a small step forward your goals and see her reaction. Then, one more step and see her reaction.

By reading her reactions you will understand what she wants and thinks.

She is young, 38, therefore, she might be naive and take you very seriously. I mean it is easy for an older woman to fall in love with an younger guy. If she was in mid40s, she would take things much easier and just have fun/sex with you.