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


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  • Author
Posted

I will definitely update this thread.

Thanks. I've put a bit of effort, but probably will require oodles of more effort if I'm in that 3rd "scenario".

 

Let's see how it plays out.

  • Author
Posted

I'm actually thinking of speeding this up and just sending her a text later tonight asking how she's been and basically saying that I'm interested in being friends for now if she wants that. Also that I don't want to impose my friendship upon her and I may have put her on the spot before with toys and everything.

 

I basically want to give her a way out and see if she takes it. That would automatically allow me to eliminate Scenario 1 and 2 and undermine Scenario 3. And it would take the pressure of her, of having a guy "chasing her" just a tad bit.

 

 

I don't know if this is smart or I should just chill and wait till Friday or next week.

Posted

Sounds like you freaked her out dude. Trying to use the kids to get in, the toys and offering to babysit sounds nice to you, but to her she's probably thinking what's up with this creepy guy. She didn't even let you into her house, you where at the doer for 15 mintues? Next time ask her out properly, do beat around the bush. Tell her you want to take her to dinner, maybe she doesn't want to go whatever boarding with you.

 

Also, what are you looking for? a relationship, long term commitment, causal.Remember she does have 3 children, can you handle that? If she's been single for three years maybe she's become very clear about what she wants and doesn't want from a relationship and doesn't have time for games.

  • Like 1
Posted
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?

 

It does sound like you are attracted to women that you can't have.

  • Author
Posted

Yes, I often go after women that aren't available because I enjoy the challenge, but also those that have a proven track record. 9/10 times good women aren't single or already have some baggage to them because they were taken early on.

 

 

So, should I just straight up ask her on a date or say I would be happy to take it slow and be friends for a while? Dating sounds like a move towards commitment she may not want right now and I am not in a rush. I can use the time to assess how I truly feel towards this whole thing. My only hope at this point is she didn't think I was creepy initially.

 

Humm.

  • Author
Posted

So, sent her a message at 10a.m ( a bit later than I liked) but curious to see what she'll reply back. Basically asked how she's doing, mentioned about my busy schedule and said that I don't want her to stress about my dating angle and I don't want to impose "friendship" on her. To that extent.

 

Really curious if she'll reply and if she does then how. I know if she doesn't answer or does something choppy she's just not interested in me and I can leave her alone. If she answers something different, especially if she talks about her week without bringing up the whole friendship talk, then I'm so in Scenario 3 or 4.Either way I feel better about myself, because I care about this girl, and if I offered my friendship and help and she already has someone she can rely on, she'll be OK.

 

So, win/win. Or at least how I'd like to see it that way.

  • Author
Posted

Well, wadda ya know. Still didn't reply.

At this point I just deleted her number from my contact so I don't do anything stupid and write to her again and make myself look foolish.

 

Feel a little disappointed. I think it's her loss, but she might have though otherwise. Oh well, will go for early 20's girls like I should be.

  • 3 weeks later...
  • Author
Posted (edited)
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.

 

BIN-****in-GO. Just saw him(short stumpy dude) and her driving into garage...it was 9:30pm, so he's sleeping over since she has her son with her, and I noticed the weekend before she wasn't home). I'm no Chris Evans but definitely better looking and significantly taller. I just don't understand why this cruel thing wouldn't tell me she's dating another guy so I stop with my offers on a date.

 

Well, it doesn't make me feel better that she didn't exactly like me because of me. This kinda feels worse.

 

Felt really sad for a bit. Hope a shark eats her. :sick::p

 

P.S. Didn't want to post, but felt obligated to update since I said I would.

Edited by mrgoodcat
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