I'd Like Some Lady Advice(Long Read Ahead)*Update 4/20/17*

[triplethreatmark]

FAN, I was wondering if I could get your advice regarding this situation I'm dealing with.

So basically, here's the thing:

A few months ago, I started working for a very important government agency(let's just say they manage air travel in the US) as an engineer. Anyways, I met this lady whom I'm seeking advice about on my first day of work. We both started on the same day. My first impression of her was that she was cute and nice enough but that was it. Anyways, I noticed that she actually seemed very willing to engage in conversation(which is odd because it's usually the opposite for me). Anyways, one day we had gotten to talking about tv shows and she asked me what I usually watch. I've been a huge Adult Swim fan since I was a teen and still watch a lot of AS shows. Anyways, we both started bonding over classic AS shows like Aqua Teen, Harvey Birdman, Space Ghost, etc. I had also mentioned that I'm a MST3K fan and she got a huge kick out of that. Anyways, as a lark(and actually half serious as a gauge of whether this person will get my kind of humor), I had suggested that she check out The Eric Andre Show. I didn't expect her to check it out at all (because of the off-color humor and the content on the show); but lo and behold she got back to me a few days layer saying that she had seen a few episodes and had liked it. At this point, I knew we could be friends but didn't really feel any sort of romantic feelings for her.

Anyways, a few days after our TV conversation, she had asked me if I was into board games/tabletop gaming. As luck would have it, I was(and still am) trying to get into tabletop gaming and we bonded a bit more over that. I asked her for suggestions and I would ask her for feedback on some games I thought were interesting, etc. For a few weeks, work got a bit hectic and we couldn't really have a solid conversation for a while. However, if we saw each other in the hallway we'd exchange pleasantries but really nothing more. At this point, I was sort of starting to develop some kind of feelings for her; but nothing too serious yet.

Well, just a little over a month ago, out of the blue, she flat out invited me to grab a drink/bite to eat and teach me how to play Dominion. I accepted the invitation. As we were planning how to keep in touch(i.e. exchange phone numbers), she very willingly gave me her phone number to contact her despite the fact that I volunteered to give her my number first. So, at the end of the week, we went out and we had a great time. I got to know her much more on a personal level and the same occurred likewise. It was while we were drinking/eating that I really fell for her. Throughout the night she seemed really attentive(like staring right through me almost) to what I had to say and she laughed at all my dumb jokes. After our meal she invited me back to her place to play Dominion with her friends. We all had a blast and at the end of the night I casually asked if she wanted to hang out again sometime soon and she very happily agreed to do so; although we didn't really set forth a solid date or time.

Fast forward about a week later and she asks if I wanted to go out again to more or less do the same thing we did the week before. I obviously say yes again; except this time we were going to meet a a local brewery and play some more board games there over some beers. The evening this happened we were going to be joined by a friend of hers later on; so we had a good 2 hours to ourselves to chat or whatever. Suffice to say, lots of flirting and playful teasing took place. Anyways, the friend eventually showed up and we all had a grand ol' time.

Fast forward again about three weeks to two weeks ago. Unfortunately our scheduled had gotten busy again with work and we didn't hang out for those few weeks in between; but I managed to ask her out to join me for the first day of the Grand Prix of Long Beach(the big Indycar race held every year here in Southern California) which happened this past Friday. At first, it seemed like it wasn't going to happen because she still had her taxes to deal with and I guess she was having some sort of issues with he roommates that she wasn't too clear about(I didn't ask any further than what she told me). However, she seemed really stoked on the idea and was really curious to see what the race was all about(Note: I go every year as I'm a big motorsports fan). Well, to my surprise, she went out of her way to join me on Friday; despite the fact I had made it clear that I understood if she couldn't make it because of the things she needed to take care of(which were more important than the race anyway). The mood between us seemed more relaxed; not as romantically tense as the other two times we hung out. Although, I must note that we had a little bit of an awkward moment(although it was one of those cutsie awkward moments) trying to decide where to eat. Other than that, everything was great and she seemed legitimately interested in learning more about how the race cars worked, why I'm so into motorsports, how long I've been going to the GP, etc. At the end of the evening, she told me both in person and over text that she had a really good time and that she was glad to have made the trip out to the Grand Prix. I also(foolishly, in retrospect...maybe) said no to her giving me a ride back to my car, which was parked a block away from where she parked(which is why I said no without really thinking it through). We also made plans to join up after Easter to play Dominion again.

Oh, I should also note that in between these times we've hung out, we have been texting. It too consists of lots of flirting and playful banter. Although it's not like we text back and forth everyday however. In a given week, I'd say we have text conversations about three or four times a week. So, yeah, there's that too. We also go out of our way to talk for at least 5 to 10 minutes everyday while we're in the office(Which is becoming less and less frequent as I'm out in the field a lot now. More on this in a bit). Also, she has gotten really into giving me the, as I like to call it, 'buddy-buddy' should jab with her shoulder lately. I also notice that she walks really close to me when we walk and talk(Although I'd be remiss to not mention that I also try to walk really close to her as well)

Everything seems peachy, right? Well, here's where the issues arise. First off, she's older than I am. Much older. Like, two thirds of my life older(I'm currently 24 and she's currently 40). A few years ago, I tried to go out with someone much older than I was(I was 22 at the time and this other person was 36 then) and it ended badly. After I had asked this other person out on a date and she said no; the friendship ended right there. I haven't seen or spoken to that person since. This was awful despite the fact that myself and this other person knew each other exclusively outside of work. This leads me to my next point.

Some of you may remember that last year I also tried getting into a workplace relationship(in a private company in a different part of the country) that ended up being a complete disaster zone for a variety of reasons. It was so bad that I had sworn off every pursuing a workplace relationship ever again. Yet, here I am a year later, trying to get into another possible workplace relationship like an idiot.

Despite our seeming compatibility(even on a friendly level), there are some very huge differences in lifestyle that may hinder any sort of relationship beyond friendship. First and foremost is religion. This lovely lass I have a crush on is a bit of a born-again Christian after some sort of bad party/drug phase in her 20s(so bad she flunked out of the University of Michigan before getting herself back together and graduating from the University of Virginia a few years after her issues at UM). I am actually very non-religious to the point of being a borderline atheist. I also drink. A lot. Also the music scenes I'm into(extreme metal and hardcore punk) tend to be a bit...skeptical of organized religion; especially Christianity to say the least. This might be a problem.

Above everything else though, I question whether she likes me back or not because I have very low self-esteem and have a long standing self-loathing problem. I'm usually shocked and a bit bothered that anybody would find me attractive or have romantic feelings for me. Like, why me? I'm f***ing terrible. I've also never really had a girlfriend or been involved with any woman before(outside of a few bad first dates and the pseudo-relationship I was in last year) in my life. So the fact that I'm trying to possibly be more than friends with someone way older(and more than likely more experienced) than I am is nerve-wracking and allows that self doubt to creep in.

One last note on this epic I've written here that makes me have doubts about whether my feelings for her a reciprocated for me. She's a very friendly person overall and she goes out of her way to really get to know the other people in the office. As I mentioned at the start of this post, she and I started at the same time with a large number of other new hires(much closer to my age). She also sits really close to them and talks to them all the time. I sit on the other side of the office away from most of the other new people that were hired. Although, as far as I'm aware, I'm the only person in the office she hangs out with outside of work so far. Although, given the nature of my job, I'll be doing a ton of traveling very soon. A lot of this traveling is for more than a few days. Usually, my trips will be weeks or sometimes even months long. She will more often than not be working from our local office. I'm afraid that being away frequently will squash any sort of romantic feelings that might possibly be shared.

So yeah...where do you think I stand here? Am I barking up the wrong tree here? Should I pursue something further like I want to? This is such an odd situation that I don't really know what to do here. I recognize that the final decision is ultimately up to me. However, I don't want to ruin the friendship or make things incredibly awkward.

If you've stuck around this long, I sincerely thank you.

[mattperiolat]

Best advice - don't make it something it's not. Clearly, there's a spark, which is awesome. But you are also level headed enough to see the obstacles - religious differences, a slight age gap, and so on. To expand on the advice, just let it be a while. Don't rush into anything. Hang out, build a bond, date a while, see if it's a fit. If it is, obstacles can be overcome with understanding. Just don't make them change and don't let them change your core beliefs.

In the words of Langston Hughes, just... be.

Wish you luck, mate. If you don't mind and it doesn't get too personal, keep us posted. You have support here.

[beamanhogan]

You seem to like her. Go for it. The worst case scenario is that nothing happens in the end and you were not meant to be. The upside is that you might meet someone that you want to be with for the rest of your life. I would take the upside every time. I wouldn't worry about the experience. You won't gain any unless you go for it.

As for the religion difference, don't worry about it. If it is an issue, it will come up at some point. You can deal with it then. I know plenty of people that do not share the same religious views and are very happy with each other. If it was meant to be, it will be.

[Mozenrath]

I've known people who have kids who manage to keep religions separate, so you may be putting the cart before the horse to worry about that.

[Dr. T is an alien]

My advice is to keep on going on. You clearly seem to like her and it sounds like she enjoys your company. Keep at that, evaluate where things are going, be open to things changing, and keep an open mind while keeping your eyes on any potential obstacles. That's not to say that you cannot be a bit proactive. You guys work at the same place so inviting her to lunch isn't outside of the norm. If it has the potential to be more than it will evolve that way naturally.

I do have one slight concern, however. You mentioned that this isn't the first time you contemplated a relationship with a moderately sized age gap. I just want to be sure that you are interested in this woman because you are legitimately interested in her and not because she fits your type. Bear in mind, I am not being judgmental either way (after all, who as a young man hadn't fantasized about boning the hot teacher or your classmate's hot mom?). I just want to be sure that you are contemplating pursuing a relationship for reasons that can be a strong foundation for a relationship. After all, that seems to be a concern of yours as well, even if you did not put it in those specific terms.

["Magic" Mark Hurr]

All great advice. You're very observant, analytical, and careful at your age which can throw someone off even if they don't show it. Even with all of the communication it may seems like you haven't played you hand yet. If she has had an involved past that required some time to rebuild, she may still be reconstructing how to emotionally respond to other people's actions when it comes to how they interact with her. Chances are she may enjoy how you are treating her, but may not fully trust it. Or she may be just comfortable with how things are on the level you're at. The age and religion factors are always a 50/50 deal. They may be requirements to take it to the next level or not that big of a deal in order to explore the posibilities. I say have an open face to face conversation with her about it. It's healthy to get this out of your system. And if you want to be friends regardless, reassure her that either answer won't change what you both have. Even if it will, you'll feel better addressing it before you yourself get too invested.

I recently dealt with a sitaution where a woman and I were mostly compatible, but she's very religious, has an older son, and recently divorced. There were other things aside from how well we got along. I've spoken on this before when this was in it's earlier stages. I had to ackowledge my part in her journey and let her have the keys on this one out of respect of her very involved situation. We were neighbors and then she moved to to another unit. It didn't feel to me like us being anything more than what we were was necessary regardless of me want to progress it into something futher. I also felt that a slight change in the circumstances that started our thing may have given it a false feel of something solid. The constant communication even slowed down on her end before i thought about taking a count out. Could be a relationship of connvenience. The funny thing is that I could be totally off on bowing out. If it there was something actually there, it'll show itself.

[triplethreatmark]

Thanks everyone for the advice. I appreciate it. Based on your answers, I've kinda heard the same thing in my private life having asked my older sister and a few close friends.

Dr. T is an alien to answer your question, the fact that two of the three most recent people I've had romantic feelings for being much older than I am is pure chance. I don't necessarily have a preference for older women. In fact, the pseudo-relationship I was in last year that ended badly was with someone about 18 months younger than I am. I think it's just that I tend to run with an older crowd than most people my age. A huge portion of my close friends are at least two to three years older than I am. I've been one of; if not the youngest guy in the office at my past two jobs(including this one). I've also noticed that I seem to click with people in their late 20s and 30s a lot in social situations. I guess as a few of you have said(and actually a co-worker of mine said this to me the other day) that I come off as a bit more mature than I actually am.

By the way, I didn't mention this in my previous posts, but she has let me know a few times that she enjoys my self-deprecating and dark style of humor(Although some of that is actually a cry for help regarding my own personal demons veiled as a joke. However, that's an issue for another day.) and really enjoys talking to me. Which is great...but like I said; she's just a really nice person overall. I'm not sure if she is just being polite and friendly or if there's more there. Damn you, Midwesterners ,for being so hard to read sometimes!(She's originally from Michigan if that wasn't made clear in my OP. I'm a Southern California kid; born and raised).

[Fade]

I've never been with an older girl so, forewarning there but..

- Age ain't nothing but a damn number.
- your guys courtship (maybe friendship) sounds incredibly f***ing cute and natural. Shits rare.
- Do not let the religion thing affect you. At all. I say that as a non-religious person.
- Get the hell away from the self loathing thing brah. I say that as a self deprecating person, f*** no, take pride. Sounds like ya got a killer job and ya got this girl you're attracted to kinda swooning.
- only issue I agree with is the "we both work together thing". I've done this many times..and..yeah..I agree. BUT..
- You'll be traveling soon right? My advice is don't rush or try and force anything..because it sounds nicely paced out..but maybe try and set up something for you guys before you start traveling (besides the Easter thing).
- if ONE of you makes a move, and the other is reciprocal, you're f***ing set mate.
- if no move is made, don't worry about it, enjoy your time with each other as usual and go about your life and do you brother. And if ya do, I feel both of you will find your way back to one another.

Godspeed dude

[triplethreatmark]

Apr 12, 2017 3:03:32 GMT -5 Fade said:

I've never been with an older girl so, forewarning there but..

- Age ain't nothing but a damn number.
- your guys courtship (maybe friendship) sounds incredibly f***ing cute and natural. Shits rare.
- Do not let the religion thing affect you. At all. I say that as a non-religious person.
- Get the hell away from the self loathing thing brah. I say that as a self deprecating person, f*** no, take pride. Sounds like ya got a killer job and ya got this girl you're attracted to kinda swooning.
- only issue I agree with is the "we both work together thing". I've done this many times..and..yeah..I agree. BUT..
- You'll be traveling soon right? My advice is don't rush or try and force anything..because it sounds nicely paced out..but maybe try and set up something for you guys before you start traveling (besides the Easter thing).
- if ONE of you makes a move, and the other is reciprocal, you're f***ing set mate.
- if no move is made, don't worry about it, enjoy your time with each other as usual and go about your life and do you brother. And if ya do, I feel both of you will find your way back to one another.

Godspeed dude

Thanks for your insight, dude. I really appreciate it.

However(and I say this generally speaking), does anybody else think that if I wait too long(assuming that my feelings for her are reciprocated for me) that she might move on? I say this because she might not be of age anymore to deal with and continue to play the flirting game for a long time like someone my age might want to do.

[Dr. T is an alien]

Apr 12, 2017 8:45:46 GMT -5 triplethreatmark said:

Apr 12, 2017 3:03:32 GMT -5 Fade said:

I've never been with an older girl so, forewarning there but..

- Age ain't nothing but a damn number.
- your guys courtship (maybe friendship) sounds incredibly f***ing cute and natural. Shits rare.
- Do not let the religion thing affect you. At all. I say that as a non-religious person.
- Get the hell away from the self loathing thing brah. I say that as a self deprecating person, f*** no, take pride. Sounds like ya got a killer job and ya got this girl you're attracted to kinda swooning.
- only issue I agree with is the "we both work together thing". I've done this many times..and..yeah..I agree. BUT..
- You'll be traveling soon right? My advice is don't rush or try and force anything..because it sounds nicely paced out..but maybe try and set up something for you guys before you start traveling (besides the Easter thing).
- if ONE of you makes a move, and the other is reciprocal, you're f***ing set mate.
- if no move is made, don't worry about it, enjoy your time with each other as usual and go about your life and do you brother. And if ya do, I feel both of you will find your way back to one another.

Godspeed dude

Thanks for your insight, dude. I really appreciate it.

However(and I say this generally speaking), does anybody else think that if I wait too long(assuming that my feelings for her are reciprocated for me) that she might move on? I say this because she might not be of age anymore to deal with and continue to play the flirting game for a long time like someone my age might want to do.

That's why small moves aren't bad. As I mentioned before, lunch dates are innocent enough if you are wrong about her interest but are still an expansion of the parameters of your current relationship. If she seems a little put off by the offer, then she may simply see you as a friend whose interests align.

[Hit Girl]

So far, so good. Just take it slow and see how it goes. Don't worry about age and religion. Passion overcomes that.

[mattperiolat]

Apr 12, 2017 8:45:46 GMT -5 triplethreatmark said:

Apr 12, 2017 3:03:32 GMT -5 Fade said:

I've never been with an older girl so, forewarning there but..

- Age ain't nothing but a damn number.
- your guys courtship (maybe friendship) sounds incredibly f***ing cute and natural. Shits rare.
- Do not let the religion thing affect you. At all. I say that as a non-religious person.
- Get the hell away from the self loathing thing brah. I say that as a self deprecating person, f*** no, take pride. Sounds like ya got a killer job and ya got this girl you're attracted to kinda swooning.
- only issue I agree with is the "we both work together thing". I've done this many times..and..yeah..I agree. BUT..
- You'll be traveling soon right? My advice is don't rush or try and force anything..because it sounds nicely paced out..but maybe try and set up something for you guys before you start traveling (besides the Easter thing).
- if ONE of you makes a move, and the other is reciprocal, you're f***ing set mate.
- if no move is made, don't worry about it, enjoy your time with each other as usual and go about your life and do you brother. And if ya do, I feel both of you will find your way back to one another.

Godspeed dude

Thanks for your insight, dude. I really appreciate it.

However(and I say this generally speaking), does anybody else think that if I wait too long(assuming that my feelings for her are reciprocated for me) that she might move on? I say this because she might not be of age anymore to deal with and continue to play the flirting game for a long time like someone my age might want to do.

Do not panic, do not rush. You two are doing fine and things seem to be progressing. Don't overthink and assume you know how she is thinking and feeling. Just be yourself, keep doing what you are doing, watch for clues and let it ride.

["Gizzark" Mike Wronglevenay]

The first reply to the thread gave you the ideal advice.

And the one thing I will add is that you need to look into reconciling someone's personal faith with your own feelings about organised religion. I doubt I can say more outside of a PM.

[Bo Rida]

I didn’t pursue a relationship with a colleague due to the age gap (younger though) and potential awkwardness. Yet that resulted in a lot of tension between us so now things are awkward anyway.

So if things are going to be awkward either way maybe it's best to go for it.

[Brandon Walsh is Insane.]

You're the prize.

You're on the right path. She wants to hang out with you for you.

Enjoy your time together, start with playful touching, and move on from there. If it's welcomed, you'll know. If not, you'll know.

You do you, you're doing great!

[fw91]

go with you're instincts. you seem level headed enough to make the right decisions here.

[No Longer a Produceman]

While most everyone here is generally positive, I personally live by the adage "don't crap where you eat." In my personal experiences workplace relationships hardly ever work out, and, when they go south, things go to hell rather quickly for both parties involved. Know what you're getting into if you decide to pursue this and expect the ramifications if things don't go your way in the long run.

[abjordans]

Dude, I read every word of that while sitting on the toilet at the gym. It honestly sounds like you are laying all the cards on the table about the situation. You should go for that. Sounds like she digs you. It sounds like she is into you and to have a girl into you AND that likes all the stuff you like is pretty rare honestly. I usually have girls that like me despite the dumb shit I like. You are 24 years old and you need to deal that deal.

I honestly think office romance is more accepted in 2017. A lot of people I know in this day and age date people they meet at work. We spend so much time there these days it is inevitable. I work in a large office, there are legit 3 or 4 office romances in my department. 2 dudes who sit right across from me date girls in the office. I have dated girls I work with and work never ends up being the problem. It is kind of normal now.

[Deleted]

When I was reading it before the sudden shift when you stated your reasons you're afraid. I was asking myself constantly "WHY AREN'T YOU TWO f***ING ALREADY!" The way you wrote it seems like you two have more sexual chemistry than The Rock and John Cena. But seriously just go for it. I'm in a happy long term relationship with a girl for the past 9 months who I can see myself marrying and we two have very different political opinions. Hell my parents are still together and they practically have very different opinions on religion and organized religion.

I get that you have a fear of failure and fear or drama and a low self opinion. I can't give advice on that but I do think it's sometimes better to try and fail then not try and what if. Maybe if this does indeed fail you may get more self confidence in the end of the day. But I think you should't hide from your fears to live and experience a bit. Relationships are a give and take and she seems to already be taking in what some of your giving like seeing Motorsports with you or checking out Eric and Andre. You might have to do the same thing with her in cutting back on drinking. Not saying stop drinking completely but a little big less. I don't know I'm guessing you play these things by ear and instinct anyways.

Actually one of my best worst relationship was with a lady 11 years older than me. Its definitely a learning experience in hindsight and a relationship I was glad to be a part off.

[triplethreatmark]

So if somebody out there cares, I have a bit of an update on the situation between myself and the lady I have a crush on:

I sort of embarrassed myself last week in front of my crush. To give context, towards the end of the day last Thursday(just about the last half hour of the day), I decided to walk over to her cubicle on the other side of our office. As it was Easter weekend, she had told me earlier that week that she was going to spend the weekend in San Diego with some family. Thus, I walked over just to wish her a safe and fun trip. As I get there, I notice that she's Facetiming her family(in Michigan) as it was her mother's birthday, I believe. I should note that I had no idea that she was calling her family before I walked over there. When I noticed, I immediately felt embarrassed beyond belief and left after a short apology. However, despite it all kind of being a blur, I do remember her giggling at the whole situation and the fact that in my nervousness did this weird shuffle thing before I walked back to my cube.

Anyways, later that evening(away from the office), I texted her a more formal apology. I also told her how embarrassed I was for just walking over without asking assuming she would be free to talk. Well, she accepted my apology and then apologized to ME about accidentally making me feel embarrassed(when she obviously didn't). She then proceeded to tell me that she got a real kick out of my nervous shuffle("A really smooth exit, lol" were he exact words). She then proceeded to tell me that I'm always welcome to come by her cubicle. I wished her a safe trip and she thanked me.

Here's the real big development. Please let me know if I'm reading way too much into this or if I have a reason to feel like I'll describe in a bit. So this past Monday night, I sent her a text asking how the weekend went. In that conversation, she invited me to the house she's staying at to play some more board games with some friends on Saturday. However, what really tipped me off was that she mentioned that the family she's rooming with won't be there at all. She also didn't mention any of her other board game friends by name and I met quite a few of them the first two times she and I hung out. Also, right before inviting me, I had mentioned that I restarted playing The Last of Us and that she'd get a real kick out it because of the similarities between it and The Walking Dead(She's a big fan of the show, if I hadn't mentioned). Well, anyways, she then(without my prodding) mentioned that I could bring my PS4 with the game to check it out and give the game a try. I told her that I would.

So after the invitation and the facts I laid out, am I wrong to feel like this could possibly be an attempt to get me to be with her alone in a private setting? I'm pretty confident that it will be the complete opposite and it'll be a bunch of us there. However, maybe I'm stupidly trying to convince myself that it'll be just me and her because deep down that's what I wish it would end up being. Regardless, I feel pretty scummy thinking this. Why do I do this to myself?

Well, anyways, thanks in advance to anybody who wants to impart any insight on these two recent developments