How to Win the Heart of a Single Mom?

[JRICHARDS1996]

Long story short, there is this girl at one of my classes and I have a massive crush on her. She is about 23 and is a single mom. She has a daughter that is almost 1 years old. My question is, how do I win her heart? And how do I navigate the added burdens of dating a single mom?

I have absolutely no problem whatsoever with taking things at her pace, or even helping take care of her daughter. If we ever had a serious relationship, I would just as soon adopt her daughter as I would marry her. I would love her just as much as if she were my own biologically.

I like single mothers. Maybe it is because my own mother had me young, but I like them very much. Plus I am extremely adept with children because I'm the oldest child, and I feel like I can kind of relate with single mothers because the family life is all I really know as well, which I again credit to being the oldest child.

What is the best way to win over the heart of a single mother, and to show her that I love her? Is it spending time with her daughter? Offering to babysit? Purchasing her groceries and/or helping her navigate work and school? I want to be able to provide her with her own "happily ever after."

Not to mention she is very beautiful and athletic. I want to see her in a thong so badly. Would a single mother be willing to do sexy things like that for me if I am a good guy to her and her daughter?

What should I know about dating a single mother?

@snowangle @CheerGirl38139 @Stacyzee @nalaa @Eevee2026

Updates

+1 y

@Puppylove94

I also love how single mothers are so mature, and seem very less judgmental than a lot of other women my age. They've been dealt a difficult hand in life, but in turn they seem more understanding of reality and the imperfections of others like myself.

[OlderAndWiser]

When I was 29 years old, I dated a woman - Gwen - who had two children. She had a son, age 5, and a daughter, age 7. Both of them were little cuties! They got their good looks from their mother. She always had a smile and was a very cheerful soul.

Gwen was a hair stylist, living in a mobile home, no support from the deadbeat dad. I was a second year law student working in the state legislature while going to school.

Gwen was a very attractive lady and she had all the charm you would expect from a modern Southern belle. Our relationship became intense fairly quickly but I was not alarmed by that. She seemed to be very satisfied with all aspects of our relationship.

I became attached to the two children, especially the little boy. I spent time playing with him when I picked up Gwen for a date. He very obviously wanted a daddy in his life.

As suddenly as our relationship started, it stopped. Gwen started ghosting me. After a few days of phone calls going unanswered, I went and waited by her car when she got off of work. What I learned from her, and later from acquaintances, was that Gwen was addicted to cocaine, she was afraid that I would find out and reject her so she rejected me first. Essentially, she thought that I was too good for her. I did not feel that way but I could not persuade her to resume our relationship. I never got to say goodbye to her kids as I never again saw them.

I learned several lessons from this experience:

1. My initial impressions of someone can be very misleading or incomplete. It is best to hold back on the feelings and not rush headlong into something.

2. When dating a woman with small kids, it is best to not be involved with the children in the early stages. It is unfair for the kids to have a stream of men coming in and out of their lives, getting their little hearts broken because mommy broke up with the guy they liked.

3. There is not always something you can do to change someone's impression of you.

In addition to those words of advice, at this point, you can't show her that you love her because you don't. You may feel a burning lust for her and you may strongly like what you know about her, but you don't love her because that requires really knowing someone, knowing their faults and still wanting them.

Also, beware rescuing needy women. If a woman loves you because of the money that you spend on her, that ain't called love! Let her know that you'd like to spend some time with her.

CONTINUED

[OlderAndWiser]

If she protests that she can't because of her daughter, offer top pay for a babysitter. If she still protests or finds excuses. . . there are plenty of other cute girls in this world!

Remember your last experience and proceed cautiously; please don't set yourself up to get hurt so badly.

[FatherJack]

Low self esteem women are not worth it , simply because they think they don't deserve anything good happening to them.

[OlderAndWiser]

@FatherJack Agree. Of course, every single mother is not a low self-esteem woman but I think it is more common in that group.

[Anonymous]

You are getting way ahead of yourself. You don't need to show her you love her. You shouldn't love her yet. You don't know her. If you act like you love her, she will REALIZE you're in love with an image of her, NOT HER, and hate it.

You're projecting SO much on her right now it's crazy. See her as she is. If you learn over time she's awesome and you fall in love with her, great. Right now you are in love with your idea of her.

Your first challenge is to get her to find you attractive and desirable.

You can worry about convincing her you're a decent guy and can handle a relationship with a single mother after that.

If she says -anything- about being a single mother, just say you know, you have a positive impression of them because of your mother, who you admire. Then shut up. That's -it-.

No, do not try to friendzone be a babysitter first. Guys hook up with the nanny, not women. Show her you're a man first. Show her that when she wants to be more than a mother, she wants to be a woman, you can make her feel that way. And if things get more serious, yes, show her you can be a father as well. BUT NOT YET. If she asks, you can just say if that's where things went, you'd welcome it without hesitation.

But to start with she needs to want to hand out with you and make out with you and show you that thong. That's not based on your father skills, not at this stage.

[justagirl5]

I think you're getting too anxious about sex (i. e. wanting to see her in a thong) and less about actual genuine feelings, which I admit is a problem a lot of guys have. I know I wouldn't do "sexy things" like that for a guy until I was 100% sure I loved him, and it may be the same for other women, single or not.

You can't necessarily do anything to "win" a woman's heart. She's either gonna be into you or she isn't. Try being friends first though. Don't come off as too strong too soon because that's creepy (trust me, I've had guys ask me right upfront for my number without barely getting to know me and I was really freaked out... it still happens and I deny every one of them). Just get to know her as a person and then decide if you're interested. The guy I fell in love with didn't do anything but be himself. It's not as hard as you think. Like I said, she'll either like you or she won't. But I recommend just being friends first and don't talk about romantic relations until later on... and that's only if she shows signs of interest.

[guysaskgirls555]

or, he can actually want to be in a relationship. I dont think thats a problem ''alot of guys'' have rather people assuming thats all a guy wants. There are an equal amount of girls going off lust, but this guy may actually be interested in her. I hope you always dont jump the gun and come up with outlandish conclusions all the time

[snowangle]

Alright dude, I like you a lot and I've enjoyed talking to you on here. So understand that I mean this with the utmost of caring.

Slow down, bro. Really. You say you love her but it sounds like the only things you know about her are 1) she has a young daughter, and 2) that she'd look great in a thong. You're getting way ahead of yourself. Don't pursue her just because you want a family and someone to provide for right now. It just sounds a lot like you're idealizing her to your fantasies and your idea of a happy future - which I know because I'm guilty of doing this A LOT.

If you really want a relationship with her, talk to her. Get to know her. If there's something there, start dating her. And THEN you can tackle the whole daughter thing. Don't start buying her groceries right off the bat. Just slow down. You'll have a family someday, maybe with this girl or maybe with someone else.

Good luck buddy.

[RustlingJimmies]

Millennial's confuse love with infatuation.

[lightbulb27]

@snowangle nailed it. You described your own inner psychology of attraction... in this girl you relate her to your mom... you love your mom, and so you feel strongly for this girl. But... you don't know this girl at all really, you are just in attraction phantasy. We all do this... Telling you to slow it down is like telling a hungry kid eating chocolate cake to slow down... I know it isn't easy, but just try to humanize her a bit and realize she is imperfect.

The best way to win her heart is to be good with her daughter and love her as your own.

I'm temped to say get a counselor to talk to just to bounce things off of in how this all goes. I think you will learn a lot about yourself and relationship. Counseling doesn't mean there is a problem (we all have problems), just helps to have someone to see you the way you cannot. GAG can do that to some degree. Good luck with them!

[Jennie6993Vali]

@lightbulb27 I'd go for her babe if you like her then don't pass it on I'd rather be with the person I like and let them do what they want wen they want I love when I have a sexy girlfriend who goes out without me and sleeps around and plays around. the stories she tells me when she gets home are amazing. sometimes she even brings some guys home with her for a after party with her. And the best part of it all is when they all cum on my sweet girlfriend. All there man hood all over and in her when she comes to bed finally she even let's me have a bit of a taste sometimes

[lightbulb27]

@Jennie6993Vali can you clarify what you mean by I'd go for her baby? you really like having a girlfriend that plays the field? I don't live in that... it sounds very "animal". you are either trolling or have a viewpoint I don't understand.

[Jennie6993Vali]

@lightbulb27 if I had a girlfriend I'd let her do what she wants as long as there's communication between both of us. a OK with me. Yea I'd let my of go out and party all night with all guys and sleep around maybe have a little gang bang. But only if she told me before or after. communication is #1 key goal for a lasting relationship. And no I wouldn't sleep around its not right the guys only get one but my wife she deserves the best xoxo

[lightbulb27]

@Jennie6993Vali you should write a mytake on your life and perspective. Its new to me, I don't get why you don't feel "insecure" about a wife mating with other guys, possibly having kidsn ot your own, lack of commitment, etc.. I've seen it in a book, but I don't understand how that occurs. My assumption is early lie experiences, but what kind?

[Stacyzee]

I notice something about you that I'll bring to light.
You're an amazing guy but you think way too far ahead into each , every and any relationship you establish with a woman.
Learn to take things day by day.
If things fall together and you both fall in love then take things from there.
What I will say at this point , there is no such thing as winning someones heart.
Either the person is mutually interested in you or not.
You can climb mountains , cross rivers and die for a person and they still will not love you in return.
Some people will never be interested no matter what you do.
Again, take things day only then will you see the potential of this relationship and what is has to offer.

[Stacyzee]

I think the core of your problem is that you expect way too much out of those who have no obligation to you , way too soon. Look how crushed you get when these women do not feel the same way. You are putting yourself up for a lot of heart wreck if you look at every relationship with that same passion, urgency and want.

[JohnDoe3000]

I don't agree with dating "experts" who basically advice people to just go on dates with anyone who's willing and you know almost nothing about and then figure out things from then on (it's way too artificial which will probably cause problems when you're ever tempted by someone else, there's no absence to make the heart grow fonder, it denies you your standards, and you won't really get to know the other person anyway because they can get away with only showing their good sides on dates).

But I do agree you have to be able to cut your losses early when there doesn't seem much mutual interest after a couple of interactions: don't plan a future together if she's never smiled at you (and you know nothing about her that could make her special anyway) and just forget about her if it seems like she couldn't care less about you after you've had some conversations. Also, show interest, flirt and stuff and don't wait forever to make a move.

[SovereignessofVamps]

I can agree with this.

[Stacyzee]

@JohnDoe3000 I know this guy on a much deeper level than you do. As soon as he visually crushes on a girl he's already thinking about ten years down the road.

[JohnDoe3000]

@Stacyzee

That sounds like a recipe for disaster and it was basically the impression I got from him as well. by the way, I wasn't really disagreeing with you, more like elaborating.

[Stacyzee]

@JohnDoe3000 Nicely put. advice. I saw you were agreeing but I thought I'd also specify that he's like that to clear anything up.

[JRICHARDS1996]

Thank you. Your answer really helped, not only in addressing my question, but helping me to really reflect and think more deeply about the nature of this situation. I will take what you said to heart, and do my best to learn from it.

[Bandit74]

Your a Rollercoaster of emotions.

One moment you're gitty with joy because you got a girl at the grocery store to give you her number. Then the next week you're writing about how all women suck then shortly after, you're apologizing, and now you're in love with a single mom who you probably don't know all that well.

I agree with Snowangle, you need to slow down.
Also, in general I dont think its a great idea to get involved with a single parent, especially not at a young age. you're young, dont waste your best years attempting to raise some other guy's kid.

[Bandit74]

You're*

[Redstang88]

Give it a week, we'll how this all fell apart and he's done with women.

[RustlingJimmies]

Would you date this single mother with children from 2 different men?

https://i.imgur.com/FwKLPsS.jpg

[Bandit74]

@RustlingJimmies
No

[Marinepilot]

@RustlingJimmies Fuck yes. Date NOOOOOO !!!

[Blonde401]

Slow it way way way down. Ask her out for a coffee (or a drink, I don't think you drink though) and actually get to know her as a person. Stop rushing stuff! Slow it way way down. Just ask her out and take it from there. There's so definite way to win anyone's heart (unless it's me and you're a nice middle aged man who owns and a dog and buys me pizza, lol kidding) you have to get to know someone, you both have to gel and make it work etc. Relationships are difficult but the easiest thing to start with is just getting to know her.

[MagiAlphaOne]

You're in that stage of the relationship where you think she is the most wonderful thing in the world. This is blinding you to any RED FLAGS she has!

GET RID OF THOSE ROSE TINTED GLASSES.

You need to get your best friends that you know that "have your back". Give them permission to tell you like it is. Introduce this single Mom to them and get their opinion. The next step is going to be VERY hard. You need to honestly listen to what they say!

This video should be the start of a "wake up" call for you!

https://www.youtube.com/watch?v=TjIubdalM8k

[Marinepilot]

JRichards1996-You and I have discussed this, many, many time. I couldn't and wouldn't EVER date a single mother again. She could be Jennifer Lopez or whoever, still a big NO just NO from me. It's way more drama and frustration
than I care to deal with. I view single mothers as used and damage and they'll be nothing more than FWBs or fuck buddies with me. Nothing more. That said, it's your choice to proceed or not. You've been forewarned about these things.
When is goes South and the Baby Daddy suddenly reappears, invariably they do, I venture that you'll be singing a different tune. You maybe psiised what I'm saying. You opened that door.

[MagiAlphaOne]

@Marinepilot, AGREED! Keep PREACHING the TRUTH!

[SoFeckinAddicted]

Lol.

Age:64

[OlderAndWiser]

@SoFeckinAddicted What's funny about a guy being 64? I happen to personally know @Marinepilot and he's one hell of a guy! Like me, he's on this site to offer some words of wisdom to those who are willing to listen. . . and most of those who are willing to listen are very appreciative of his advice.

[SoFeckinAddicted]

@OlderAndWiser This just gets funnier

[OlderAndWiser]

@SoFeckinAddicted A large part of what passes for humor is idiosyncratic.

[Marinepilot]

@OlderAndWiser Thank you.

[Darkfairie17]

I think if you want to date a single mom, then you definitely need to take things at her pace. I would just be friendly to her, get to know her. Don't try and force her to go out with you right away. Perhaps start sitting near her and asking her things about class. Then maybe move into more personal conversation.

The best thing is to remember that this woman is just like any other woman. She has her own desires and things she enjoys. So don't think that just because she's a mom that she isn't into sex or relationship stuff. If she likes that stuff, she is into it. You just have to get to know her and know what you can and cannot go with her.

[JohnDoe3000]

Why? I mean seriously, you've never dated a girl and now you want to start with a single mother? And her child isn't even 1 year old (so the break up with the baby daddy must have been recent)...

Also, you still need to work on your attitude/thinking because even after all your bad experiences you're still asking if you can win her over by doing, and even buying (come on, you should know better by now), things for her. Even when that stuff works she'd see you as a doormat/walking ATM (and there wouldn't be much genuine attraction), unless she's already attracted to you and in that case you wouldn't have to do/buy things for her.

[worldscolide]

Honestly, dont do it, There will be drama like dealing with the father and the like. That having been said, The best thing you can do is not to push, and be your self. Dont try to support her, dont reach too far. Single moms can be extremely gun shy and choosy when it comes to dating. They have to be, because they have to think about more than just them selves.

[thisGUYknows]

I didn't even read your shit but I know the answer. Be kind, be helpful but let her be able to help herself. Be a friend above all. This is the one spot where the friend zone actually helps. Single moms have their wall up high. You can't bulldoze in. Sometimes u gotta dig with a spoon. Don't be too available or desperate or she'll back off because she'll feel she can't return the same amount of potential love. And she won't. You'll always be second. Maybe even third. And u gotta be ok with it. Take your time and feel things out. With non mom's u can be a little assertive. But with single moms you gotta follow the jellybean trail if I
U know what I mean

[MaybeNot1]

If she wasn't a single mom you would've had a chance for being 20, but considering she is there is an extremely high possibility she wants an older man with a career.

[Afrochick]

yupp

[JRICHARDS1996]

I'm on the path to a career though. I have a 4.0 GPA in college and graduated high school as valedictorian. I'm also the oldest child so I know full well the burden of taking care of children.

[AssJacket]

Sorry kid, but that stuff isn't terribly important in the Real World (tm) and isn't going to be impressive to a woman.

[MaybeNot1]

You're on your way, but not their yet. Chances are she wants something serious, not only for stability but also out of respect for her daughter. That said, I doubt she'd be open to a "let's casually date and see where it goes...", she already had that and it obviously didn't work. Now she wants something stable, not only mentally buy financially also. Why? providing for the child is any mothers priority. Wasting time "dating" doesn't sound as appealing when you have responsibilities that a single person, with no kids wouldn't have. Therefore, you and her are not on the same page.

[Redstang88]

Best way to approach dating a young, single mom-
s-media-cache-ak0.pinimg.com/.../...9edfd82830.jpg

[RustlingJimmies]

oh shit it's glenn.

[snowangle]

@RustlingJimmies Glenn is FINE.

[Jeniferh21]

All I gotta say is, if you're with the mom, you're with the kid too, so if you're going to treat the kid as just her kid and not yours, fuck outa there, if it's just for fun, tell her, if you really want to be with her and her kid, tell her, simple, and you win her by winning her kid

[JRICHARDS1996]

I made it clear that I really would be willing to adopt the child if it came to that and raise her as if she were my own. I'm an oldest child so younger children really do not faze me.

[Jeniferh21]

Oh lol I didn't read the whole story because ya know I'm lazy 😁 But yeah you're good if you're willing to be also with the kid

[SheSugarcoat]

This is creepy as fuck. "offer to babysit", yeah good luck in being labeled as a pedo! lol

[Marinepilot]

You're right. Well stated.

[FatherJack]

Apply the brakes now !! I'm a single dad ( ironically raised by a single mother !! ) her child will ALWAYS come far before you , also you do not want to come across as a potential pedo , men are automatically assumed to be a potential danger to children ( I've experienced this hostility from women myself simply because I'm male ) @JRICHARDS1996 Weren't you recently burned by a stupid girl that spread false rumors about you ? As a man you have to have a harder heart , you cannot allow yourself to fall for women you don't even really know... you are setting yourself up to be either mocked as " needy / wussy " or worse , used & abused , I've learnt the hard way... keep a logical head on your shoulders !!

[md726]

I'm a single mother and I met my current boyfriend of 4 years when my daughter was 2. He won me over when he was constantly asking about my daughter, he wanted to be involved in her life. We had been dating for 9 months before I allowed him to meet her and that's when I fell in love. The way he acted with her, the way he spoke to her was perfect. He has since adopted her and she calls him daddy.

[JoyGirl]

That is so sweet. I am happy for you and your daughter. :)

[Newaza]

I would say wooooo!! Slow your roll dude! I went on like two dates with a single mom. I told her point blank I don't want to go to her house or meet her kid. She 100% agreed and she appreciated it. I don't want to barg in on some little kids life. Keep your distance dude.

But she might just want a dude to take care of her and the kid, I think that's what you banking on. Not going to lie you sound a bit desperate and creepy.

[JRICHARDS1996]

I agree. But for me it is more about my own personality. Again, I'm the oldest child, and I have never truly lived life outside the context of responsibility and having to be an adult. The notion of being free and/or having fun like a typical college kid honestly scares me, and would probably drive me to depression. I need to have responsibility, to be taking care of someone and filling an important role.

[Newaza]

You sound like a mess bro. Best of luck.

[RachelBrigs]

I just find it weird that you're giving this much thought to someone you don't know. Talk to her before you talk about adopting her kid and marrying her.

[TacosRAwesome]

My advice is that you take a chill pill and stop talking about love towards a girl you barely know. If you want to date her ask her out but actually get to know her before meeting the kid.

[MargaritaPeach]

Treat her like she is a lovely, attractive young woman. Don't attach the 'single mom' label to her as a way to gauge how to approach or treat her. She's a girl, so that's how she's like to be viewed. Not as a girl-with-a-baby. Good luck, and I hope it works out for you!

[Marinepilot]

MargaritaPeach-He;s a better man than I am. I tried dating three single mothers and
it never ended well. I can't do it for a variety of reasons. The two biggest deal breakers
were never enough alone time and ex's who were always around. Invariably the ex resented
me and made the girl mad and it spoiled what precious little alone time we had. Also disrespectful kids. I'll be fuck buddies with a single mother and a friends with benefits. Nothing more.
Some guys can date single mothers seamlessly. I can't and won't. Too many bad experiences for me to EVER open my heart to a single mother ever again.

[MargaritaPeach]

@Marinepilot fortunately there are a lot more men and women these days who are choosing not to have kids, so that opens up the dating pool for people like you. I am fortunate in the fact that I have never been a single mom, but I am sure it's a lonely placw to be. I did marry a guy who had three kids, though, so I can empathize a little with some of your experiences. Lucky for me, it wasn't a bad experience. But I can definitely understand your reasoning, based on what you have been through.

[Marinepilot]

MargaritaPeach-I am adamant about this. It's just not something I can or will do. I've
had all manner of grief over this. I've been told that a Real Man can do this. No, a Real Man
would do what he felt was right for him. I'm told I'm selfish. For not wanting to be second best?
I don't do that for anything or anyone. Especially another man's children. I want my own fresh start with a woman who has never had kids. I'll wait until hell freezes over if I have to do this. Thank you for being understanding of my views.

[MargaritaPeach]

@Marinepilot I think that it's fine, and even admirable, for you to stick to your guns on this one. Do what makes you happy. Life can get so complicated sometimes; by laying ground rules you have made it decidedly less so. And it's not like you are degrading single moms or refusing to associate with them. You wrote that you are still willing to sleep with them. You just don't want to be tied down by their baggage and drama. There is nothing wrong with that! Men that know what they want are awesome.

[Marinepilot]

MargaritaPeach thank you. You are the voice of reason.

[misterfit]

I've dated a single mom and would prefer to avoid it. Keep in mind if you get attached to their kid it'll be very hard on you and the child if you break up. With single mothers take it very... and I mean VERY slow.

If she brings you around her child too quick, she's giving you the hint that she wants your support.

If she doesn't do that, then she's trying to get to know you and she's interested.

One last note, you're projecting what you want on her. She is probably not the girl you imagine her to be and you are putting her on a pedestal. Get over that so you can really see if you actually want to date her.

[meatballs21]

Her cuntspawn has to like you.

You have to accept that you are second banana to the above.

Also... don't go into this unless you are serious. If you just want to see her hot athletic body in a thong, have some fun with what's inside the thong, and then leave... do yourself, her and her kid a favour and don't. Unless she's specifically said that she's just looking for fun, it's not going to be enjoyable for her or her daughter to have random douches coming and going.