Trying to Date an Older Single Mom....Just Asked Her Out Sorta...(long read)

[mrgoodcat]

Hi folks, so now I'm 26 (my last thread of loveshack was when I was trying to steal this 17yo girl from a new guy she started dating...I was 23 back then). Now I am really into a 28-29 year old single mom with a 3 year old child. She lives in my building and we've always been friendly, but nothing truly to it- she smiles at me and looks back and I always stared at her for as long as I could. According to sources, she kicked out her husband because he cheated on her and she's been single for like three years...I guess. I don't know, actually, maybe she has a guy she is dating, but like I said, I don't believe so and sources say she does not.

 

I've thought of asking her out for almost a year, but thought that I probably am not ready for this kind of step due to her being a single mom and everything and uncertain about situation with ex-cheater hubby(I didn't know that was the case back then).

 

Then two days ago after some soul searching I asked to see if I can drop by some toys for her kid that I supposedly bought for someone else. Did exactly that in the evening. Her boy was excited about toys and went on playing and we talked in the doorway for probably 10-15 mins. I started casual, not suave at all- just jumble about building and what not and then finally led into if she tried doing some water sports and other things and asked if she'd be interested in paddle boarding with me as a fun exercise(I have a paddle board and said I was looking to buy another one). Then I mentioned that if she needs to run somewhere she can count on me to baby sit of an hour or two. Finally I wrapped up with if she "wants to talk or get a cup of coffee" after which I slightly freaked because it felt so unnatural that I kinda said "not like asking you out, but just to you know bla bla" or something like that. And she was like ok, so then I finally said here is my number, because I didn't want to say "can I have your number" and giving myself room to avoid straight up rejection and to see what she does. She got her phone and asked to write down my number. I did and she called me so I can have it too. Awesome I thought. So, I wrapped up just confirming with her that may this or next week we do something fun or just get a coffee.

 

 

So, this noon I texted her basically saying that I know she is busy and just in case she wants to go out of lunch or do something on the beach, I'll be available after such and such hours on Sat and Sun. She was home apparently, but I got no reply. Not even "ok, sure I'll let you know". Nothing. She has Iphone5 and has a text message so I'm sure she can reply or receive texts.

 

So, my plan right now is not to do anything today or tomorrow and just maybe call her somewhere mid next week (Tuesday/Wed) and ask what she is doing. If I get an ignore, then I probably missed my boat or she is still not ready for dating and I just go back to chasing younger chicks with no "baggage". She seems like she genuinely has a good heart and she's not a whorish type, but I know she is still a woman who enjoys playing games. I'm ok with games, just as long as I'm chasing another 3 girls in the meantime, which lessens the discomfort of failure. I cannot afford the time expense of chasing another 3 girls right now, so I'm a bit antsy about this.

 

Would appreciate any input and some reasonable psychoanlysis of this situation. I promise to update how this turns out, like I did with my thread back in 2011.

Edited September 20, 2014 by mrgoodcat

[sdrawkcaB ssA]

I donno... sounds like you are planning a take over. Well just too much, seems like you overwhelming her with what you have done.

 

She is older, has a child and has her set ways. If you cannot see her way of doing things, she is going to feel pushed no matter how careful you are.

 

Give her time, she is not going to run off with another guy overnight. Her priories are for the well being of her child and herself.

 

Did she ever talk to you about her past relationships including with the father?

 

That will tell you how she is with being friends or looking. If you don't see her warning signs so to speak your never going to get past friendship.

[mrgoodcat]

I donno... sounds like you are planning a take over. Well just too much, seems like you overwhelming her with what you have done.

 

She is older, has a child and has her set ways. If you cannot see her way of doing things, she is going to feel pushed no matter how careful you are.

 

Give her time, she is not going to run off with another guy overnight. Her priories are for the well being of her child and herself.

 

Did she ever talk to you about her past relationships including with the father?

 

That will tell you how she is with being friends or looking. If you don't see her warning signs so to speak your never going to get past friendship.

 

No, I never even approached the area-I've seen her husband around(genuinely didn't like the guy either). We just spoke briefly for the last year every time I saw her every week or so. Sometimes she looked overwhelmed over her issues, sometimes she looked happy to see me. I though her body language when talking to me was closed, but my head was spinning from all the discomfort I was in to read well into it. Was blushing like a tomato. And I don't take that too seriously, because how else would woman act when a neighbor guy who she knew for 4 years knocks on her door kinda asking her out.

 

My intent was to show that I'm a serious guy, since I'm younger than her and that I am not afraid to take things really seriously. That's the advice I got, but maybe I've overshot the target....

Edited September 20, 2014 by mrgoodcat

[sdrawkcaB ssA]

I will tell you this bit of advise... you will have to be a bit more mature. Forget about dating as you know it. Don't expect anything, just rely on what trust she gives you. Your not yet fully trusted. Moms will be more careful in that respect.

 

She will take her good time, and will probably make you feel things are too slow at times. Getting that first time to do something may not be taken as a date. Not that you are slipping under the radar. It is that she will keep things low key.

 

I think you are rushing too much, as she seems to have a lot to think about, since you described a situation that showed stress. Until she opens up about the father and other relationships, I would not expect anything more than a casual neighbor friendship. She'll make the move, in allowing things to progress. She may even drop off the radar for a few days or a week. Until she sorts things out, I don't think she'll be wanting to put her stress over to you and complicate things.

 

Take your time, and if she is stressed, be gentle and ask if you can do anything for her. But be careful about being to generous, as you have yet to learn who she is. Some may find an easy way to get a temporary fix if in a bind.

[HappyLove]

"I know she is still a woman who enjoys playing games. I'm ok with games, just as long as I'm chasing another 3 girls in the meantime, which lessens the discomfort of failure."

 

This came off creepy. Sounds like you're not genuine. She probably sensed that.

[mrgoodcat]

"I know she is still a woman who enjoys playing games. I'm ok with games, just as long as I'm chasing another 3 girls in the meantime, which lessens the discomfort of failure."

 

This came off creepy. Sounds like you're not genuine. She probably sensed that.

 

Not what I meant, I was genuine. I don't want to chase another two girls when I'm asking her out. I really like this girl, always have and not just from sexual point of view. That was probably secondary.

 

However, when I date, whenever I ask a girl out, I always ask another two girls out so that I'm not overwhelmed by disappointment if one I really like starts playing games. It's my protective mechanism. However, if I get serious with one, I usually end it with the other ones.

[HappyLove]

Not what I meant, I was genuine. I don't want to chase another two girls when I'm asking her out. I really like this girl, always have and not just from sexual point of view. That was probably secondary.

 

However, when I date, whenever I ask a girl out, I always ask another two girls out so that I'm not overwhelmed by disappointment if one I really like starts playing games. It's my protective mechanism. However, if I get serious with one, I usually end it with the other ones.

 

Bravo that you have the guts to ask women out. A lot of men could learn a lot from you in that regard. But it sounds like you're using women when you just ask out another two just to make yourself feel better.

[mrgoodcat]

I think you are rushing too much, as she seems to have a lot to think about, since you described a situation that showed stress. Until she opens up about the father and other relationships, I would not expect anything more than a casual neighbor friendship. She'll make the move, in allowing things to progress. She may even drop off the radar for a few days or a week. Until she sorts things out, I don't think she'll be wanting to put her stress over to you and complicate things.

 

Take your time, and if she is stressed, be gentle and ask if you can do anything for her. But be careful about being to generous, as you have yet to learn who she is. Some may find an easy way to get a temporary fix if in a bind.

 

Appreciate that. I don't mind being in her friend zone. I want to help her and be supportive to a degree, but as soon as I feel she's dating someone else, I'll vanish faster than the speed of light. I'm no stalker, but I would even consider paying my buddy to do some spying for me to save me any time and heartache if I suspect she is playing me while dating someone else.

[HappyLove]

"I kinda said "not like asking you out, but just to you know bla bla" or something like that."

 

But didn't you tell her you weren't looking to date her? Maybe she took you at your word? Anyways it's still early she may respond but you need to be more honest in your exchanges with her. I take it the toys weren't really for someone else either? Your tactics come off a bit shady so she may just be being careful.

[mrgoodcat]

Well, I had a cover for toys since my nephew had a birthday and she knows I have a nephew. So, I just said the toys I had I couldn't find so since I promissed to drop off some toys, I just bought them for her son.

 

I don't come off as shady in person. People always trust me on the phone, in person, and dogs love me. LOL

 

Just saying, shadyness is not something people perceive me off, usually.

[Tayken]

@OP.....I hope you understand how family law works? If you don't, then I'll urge you to educate yourself pronto. Most men don't, and only end up finding out the hard way, when they've been sucked it (no pun intended).

 

If you start going to the kids activities, have them on your health coverage etc, you WILL find yourself paying child support if things go south. It's called double dipping, and most single moms know of this and their attorneys will advice them to go after you.

 

So ask yourself, is this what you really want?

[mrgoodcat]

@OP.....I hope you understand how family law works? If you don't, then I'll urge you to educate yourself pronto. Most men don't, and only end up finding out the hard way, when they've been sucked it (no pun intended).

 

If you start going to the kids activities, have them on your health coverage etc, you WILL find yourself paying child support if things go south. It's called double dipping, and most single moms know of this and their attorneys will advice them to go after you.

 

So ask yourself, is this what you really want?

 

I hope you can show a good source for that claim. Living together and being married is a different thing. But seriously, I think it is a little bit too far ahead to even think about that. I will take it into consideration. In any case:

 

How Living Together Affects Child Support Payments | Nolo.com

Edited September 21, 2014 by mrgoodcat

[mrgoodcat]

One thing I'm not sure now is whether I should not contact her until she contacts me back or give her a call in 3-4 days. I can't decide what is the right thing to do. And besides, I don't know if she already has selected a suitor. I mean she can't be single for 3 years! I feel tad bit in the dark and I don't like to not be in control of situations I put myself in. Maybe I'm in over my head.

 

It's just I thought she was maybe lonely, still heartbroken, and perhaps needed a man in her life. Add to that the fact that I like her personality and find her attractive, so I thought it's not a bad idea. I also think a more serious relationship will bring me to my full potential as far as putting most in my work. I do best under pressure and with responsibility.

 

For now, I'll just wait and not expect much.

Edited September 21, 2014 by mrgoodcat

[isisisweeping]

). Then I mentioned that if she needs to run somewhere she can count on me to baby sit of an hour or two. Finally I wrapped up with if she "wants to talk or get a cup of coffee" after which I slightly freaked because it felt so unnatural that I kinda .

 

 

 

You're going to scare most level headed single moms with this much interest in their kids, offers to babysit, etc. Many are worried about the idea of being targeted by pedophiles. (I'm not saying you are a pedophile, but that sort of approach and involving with kids is going to set off red flags)

[isisisweeping]

If you start going to the kids activities, have them on your health coverage etc, you WILL find yourself paying child support if things go south. It's called double dipping, and most single moms know of this and their attorneys will advice them to go after you.?

 

*cough* bullcrap *cough, cough*

 

 

Oh excuse me, it's just allergies. I'm allergic to bullsh*t.

 

 

 

 

This is simply not true, OP. While there is a lot to consider in dating a singlemom, you probably want them to be fact based and not fearmongering.

[sdrawkcaB ssA]

One thing I'm not sure now is whether I should not contact her until she contacts me back or give her a call in 3-4 days. I can't decide what is the right thing to do. And besides, I don't know if she already has selected a suitor. I mean she can't be single for 3 years! I feel tad bit in the dark and I don't like to not be in control of situations I put myself in. Maybe I'm in over my head.

 

It's just I thought she was maybe lonely, still heartbroken, and perhaps needed a man in her life. Add to that the fact that I like her personality and find her attractive, so I thought it's not a bad idea. I also think a more serious relationship will bring me to my full potential as far as putting most in my work. I do best under pressure and with responsibility.

 

For now, I'll just wait and not expect much.

 

It is not about what you plan... your overly thinking. A person staying single for 3 years or 10 or more, is all up to them. If she is dating so be it. It is possible by the way you interact with her has shown your intentions as well as the words that have described them to us. To many expectations will ruin the best intentions. Plain and simple. She might be nice in not wanting to say one way or another what she wants. As it may disappoint you by your expectations.

[acrosstheuniverse]

Yeah it was a bit weird to offer to babysit her son when she hardly knows you, OP. She's probably concerned at the level of interest you've shown her child when you barely even know her (taking him toys, offering to babysit etc.)

 

Just give her a call in a few days and ask if she's free for coffee the following day. Don't wishy wash around 'hey, do you fancy meeting up sometime soon? Not like a date, just hang out' because that's really offputting. You already told her you weren't interested in her by telling her you weren't taking her out if you went for coffee.

 

If she's not free, and she's interested, she'll arrange another date. If she doesn't rearrange or accept, she's not interested. It's very nice and simple. I probably wouldn't even bother getting back in touch if I were in your situation, given that she hasn't replied to your messages. But maybe she's planning to reply soon or whatever.

[HappyLove]

I was trying to pinpoint what was really off putting about this exchange and I think you guys nailed it. The offering to babysit was too much. That on top of the gifts and then saying it's not really a date would make a person think twice. It's a shame because I think OP put a lot of effort into this and meant no harm. Next time run it by us here at LS OP.

 

You could MAYBE save this by CALLING her in a few days with an offer to take her to coffee. If you get VM leave a message with the offer. If she doesn't respond...on to the next one. And don't add anything else just a 10 second message for coffee. Good luck!

[ja123]

Just from your opening post, have you ever asked yourself why you're going from one extreme to the other (17 yo in a relationship to an older single mom)?

 

 

There's something here ... maybe you're emotionally unavailable, lack options, I don't know ... but, it would be a good idea for you to do some deep introspection, no?

 

 

Why wouldn't you try to date women closer to your age and in a similar stage in life?

[mrgoodcat]

God damn, I didn't even think that she can take me for a pedo. Goddamn pedophiles these days...giving every white guy a bad rep. I was pretty specific I can't babysit for more than an hour or two and that I'm not great babysitter. It was more of a courtesy than anything. Bringing toys was my way to actually get to talk to her for a bit vs. holding her up by the elevator.

 

Well, now I just don't want to contact her at all. Thanks for making weird, but maybe that's how she thought.....Oh God.... Ughh. I just hope not.

 

I did text her again saying that I apologize if it seemed like I'm rushing, and that I just wanted to show I'm serious. She THEN replied to me saying she is busy at that time and wouldn't have time. She wasn't rude. To which I replied that I get it but that she is welcome to contact me. And I said that last time I didn't get my point across cause I didn't want to embarrass her vs. being worried about rejection and that I kinda want her to know my intentions.

 

But now I really don't care what she answers.

 

Just from your opening post, have you ever asked yourself why you're going from one extreme to the other (17 yo in a relationship to an older single mom)?

 

 

There's something here ... maybe you're emotionally unavailable, lack options, I don't know ... but, it would be a good idea for you to do some deep introspection, no?

 

 

Why wouldn't you try to date women closer to your age and in a similar stage in life?

 

I certainly lack options and frankly time while I don't yet have cash to date elite escorts. I don't like going to clubs or bars, you have to weed out hookers from gold diggers and VD bar flies. I graduated college and work online, so my only options are women I see in my neighborhood or go into online dating. I don't think online dating is for me, I'm about 5-7 on a hotness scale and girls are proven to be picky online. Then there are deceptive pictures....I have been on one of those dates and after that just said f%*k it and quit online dating, only asking women out who I meet in person in my community or work.

Edited September 21, 2014 by mrgoodcat

[acrosstheuniverse]

God damn, I didn't even think that she can take me for a pedo. Goddamn pedophiles these days...giving every white guy a bad rep. I was pretty specific I can't babysit for more than an hour or two and that I'm not great babysitter. It was more of a courtesy than anything. Bringing toys was my way to actually get to talk to her for a bit vs. holding her up by the elevator.

 

Well, now I just don't want to contact her at all. Thanks for making weird, but maybe that's how she thought.....Oh God.... Ughh. I just hope not.

 

I did text her again saying that I apologize if it seemed like I'm rushing, and that I just wanted to show I'm serious. She THEN replied to me saying she is busy at that time and wouldn't have time. She wasn't rude. To which I replied that I get it but that she is welcome to contact me. And I said that last time I didn't get my point across cause I didn't want to embarrass her vs. being worried about rejection and that I kinda want her to know my intentions.

 

But now I really don't care what she answers.

 

Well that's even more weird 'I'm not great at babysitting and don't have more than an hour free to do it but honestly, if you want to leave your child with me feel free' It's just weird to offer to babysit a stranger's child whatever the situation, sorry but it is. You continued to flunk it anyway, saying that you want to show her you're serious (um, she barely knows you and you haven't been on a date yet). She show you down and said she's too busy, and didn't rearrange. You then replied telling her she's welcome to contact you (um, she already knows this, she has your number and knows you're into her due to the level of interest you're showing her) and then tell her you're afraid of rejection when she barely knows you and has shown no interest at all.

 

I would be running a mile from this. Maybe in future come here and post about how best to approach things with women if you tend to do stuff like this. If you're not experienced in meeting women and progressing things it can be a difficult process to learn to navigate but it's hard to see how you could have gotten this one more wrong so yeah, feel free to get support and advice here for the future. And leave this poor girl alone now.

[mrgoodcat]

I've known her for like 4 years, she knows my my sister and her baby daughter. I see her every week on the parking lot and always said hi and just occasional small talk. She smiles at me a LOT and I smile at her a LOT too. I really think she slightly liked me at very worst. I am also a very trustworthy person and it reflects on my face- people generally perceive me as honest individual(no, I don't wear glasses or have a nerdy look).

 

But I don't know if there will be any smiling from now on. BUT IT IS TOO EARLY IN THE GAME, not that I'm approaching it like a game even though any dating process is. I see three scenario and I'm slightly optimistic because I've done a miracle once before(it didn't last but that's because I effed up right after), and unless she's dating someone right now who she seriously likes, I still stand a fair chance. Not great, but fair.

 

Scenario 1:

 

She doesn't like me, thinks I could be a pedo, and hopes I never contact her again. I give 5% chance she thinks this. I am a transparent enough and have a sense of honesty that I don't think she perceived that I'm some weird pedo f*ck.

 

Scenario 2:

 

She already has met someone who she is occasionally dating and she likes. So, while I flatter her and up her spirits, I'm unwelcome to pursue. 25% chance.

 

 

Scenario 3:

 

She is still hurt over past relationship and thinks I'm a bit too young for her and immature and not able to fill the proper role of husband/dad. I give 45% chance of that. But this scenario is not a deal breaker because I have room to prove things.

 

Scenario 4:

 

She likes me, has not committed to dating, and wants to see how I behave from now on. She wants to know if I'm just some immature kid looking to hook up with her or I'm delusional who has fallen in love head over heals. Either way she is unsure and wants to see what I do. And it will take time. Probably a LOT of time. I think I might not get a serious date with her for another 2-3 months.

 

So, to me, regardless of which scenario is, I want to be ready for scenario 4. I think the steps for that will involve me reaching her by phone, possibly in a week and asking how she's been and if she wants to go out and talk and laugh about my recent escapades. If I get no reply whatsoever, then I know it might be a combination of scenario 1 & 2. If she texts me back or calls back(I doubt she will call back) then it depends what kind of text. If she once again says she is busy, no thanks than I know it could be #2, 3 or 4.

 

From THIS point, I can pretty much ask her where I stand. I don't see why she wouldn't tell me she's seeing someone else since it would be a quick and easy solution. If it is #3 then she could say that she's not in a dating state of affairs and she has too much going on and that she needs her time for her son. Finally, if it is #4, then the response could be similar, but she just might say I was busy THIS week and had too much going on. This means she wants to lead me on.

 

Pretty much how I see it right now and how I'll work it. I like her enough that I don't want to bother her anymore if that's what I'm doing, so I should have an answer in a week and a half. In the meantime, she can let it marinade and see how she feels.

 

Time will tell, as always.

Edited September 23, 2014 by a LoveShack.org Moderator

[moie]

scenario 1 and 2 are probably easily solvable. #3 is where you will need a lot of investment. Number 4 is doable, can you rule out the first 3 yet?

[mrgoodcat]

@moie

 

I agree, that 1 and 2 is piece of cake. I just have to see if she responds/returns my next call and if she doesn't I know I'm not welcome. Reasons aren't really important...I don't care if she has a guy or doesn't like me.

 

I feel like I can definitely rule out 1 and 2. I gave her an option of taking my phone number and instead of getting a piece of paper and pen or just taking the number down she texted me back. But that doesn't mean she necessarily wants me to contact her later on, but it's a good sign. That could mean I'm in #3 stage, she wants me as an option or maybe I am right in #4 stage.

 

Frankly, I feel like I can relatively confidently rule out 1 and 2, but not 3. 3 I will be able to rule out this Friday maybe. I'm just not sure if I should wait more.

[moie]

Alright sounds good, let us know how it goes. You deserve some reward for all your hard efforts

Edited September 23, 2014 by moie