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I'm still not over her after all these years but she has a 2 year old daughter and says she's done with dating. Should I still persevere?

Tagged as: Crushes, Dating<< Previous question   Next question >>
Question - (22 February 2018) 9 Answers - (Newest, 22 February 2018)
A male United States age 22-25, anonymous writes:

So a little backstory… I've been crushing on this girl since high school and you could say I got hit hard. I never had the courage to ask her out; because it's high school she was way out of my league back then.

I've put her in this pedestal that if I describe her… well it would be completely biased. The one thing I can say about her that I know is true… is that she was the girl who was always in a relationship throughout high school and life in general. My personification of a perfect girl (I know my judgment’s clouded) was never single and guys kept lining up her door to sweep her away. That was drama that I just don't want to handle.

After graduation, we gone through life and well we took very different paths; I moved away for college and she did her own thing. I never really stayed in touch with her again but found out 2 years ago she had a kid...the dad left her, she reinvented herself and focused her efforts in being a single parent and the future of her daughter .College was somewhat of a change for me. It gave me confidence, got the courage to start dating and basically let go of everything that’s holding me back. I started dating; I’ve had friends and well grown more as a person.

Fast forward to present time we’re both living in the same city, and I just broke up with my girlfriend. We just met again last week. We shared coffee and found out we’re just 10 minutes away from each other. I asked to keep in touch and exchanged numbers but she adamantly stated that she’s not dating anymore but that she’ll think about it.

Sorry for the story now here’s my question…. Is it okay to date a girl with a 2 year old kid? Everyone and my parents says it’s a bad idea and I should just let the fantasy of 16 year old me go but I really want to give it a shot, call her, and ask her out. It may be the break up mixed with resurging feelings upon seeing her again...and well I need to ask if you think I am thinking straight.

People say dating someone with a kid is just asking for trouble but I see people do it all the time. Thirty something couples often have children from previous marriages and they get along well. Why do people think it’s different for younger people?

I know that being a single parent is hard and she’s devoting her time and her life for her daughter but if a girl says she’s through with dating, going out, and being young…should I respect that? I feel that the time after high school changed her and made her grow up faster; she’s seen the world, while I being just out of college is just beginning to experience it. She said no dating but she didn’t say I couldn’t spend time with her. I’m willing to trade my early-mid-twenties to be with her if that’s what it takes. Plus knowing that she’s so close to me I’ll never completely forget her without moving on entirely so I’m stuck dealing with these feelings. What do you guys think? Any tips?

Thank you for reading if you managed to finish it and sorry for the grammatical errors.

View related questions: broke up, confidence, crush, exchanged numbers

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A male reader, anonymous, writes (22 February 2018):


Thanks guys...I guess I needed to hear that more. I'm sorry for sounding immature; I know I need time to process these feelings, and reading back what I've said I'm well aware of how my adoration for this girl is borderline delusional.

Everyone I thank you for your concern and I'm thinking a bit straight now. But I'm guessing that we can all relate to this situation right? Meeting your high school crush again, knowing he/she is single...I guess when she asked me out for coffee, had an hour long conversation, and said it was okay to keep in touch...I got my hopes up. I really thought it was a date, swapping numbers and offering me to "drop by sometimes" was like a fantasy to me and you could say that perhaps I needed that. I never wanted to take advantage of a vulnerable girl or make my childhood dreams come true, I just wanted to feel safe and spending that time with her did that.

When she said the part where she doesn't date anymore, well it shook me. Doesn’t that mean we can still hang out? Will it be okay to spend time with her; I didn't ask her out and she dropped the response "I don't date" as a BUT after she told me we should talk more often. So is she just looking for a friend? I guess that shouldn't be me right?

I really want to move on. I know I have my life ahead of me at 23 but still from now on: Every time I drive by her apartment…the thought of her will come to mind. Every time we meet at a restaurant she’ll be there and she’ll talk to me. Breaking up is somewhat easier as there is an effort in both sides to sever ties but for me she’ll still talk to me now, we’ll still see each other, and she’ll always be her for me if that makes sense.

Long story short I thank you for your help but I’m guessing I’m asking more questions. Should I tell her these feelings? Just so I could get my closure (which I know isn’t real) and move on or would it be okay to be friends with her even though I have these feeling? Any thoughts?

Thank you for reading this long post.

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A female reader, Andie's Thoughts United Kingdom + , writes (22 February 2018):

Andie's Thoughts agony auntYou won't take no for an answer. Red flag.

You're not mature enough to get over a high school crush. Red flag.

You don't want to be friends, so you won't be thinking as a friend if you hang out alone together. Red flag.

OP, don't be *that* person.

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A male reader, WiseOwlE United States + , writes (22 February 2018):

I see problems on two fronts. You only recently broke-up with someone; and she told you that she wasn't dating anymore.

You are motivated by the challenge of winning-over a girl you saw to be out of your league, and placed up on some pedestal. Back in the day, she didn't even know you existed; while you worshiped the ground she walked on. Now again that challenge has presented itself. She says she doesn't want to date; and again she has inadvertently rejected you. It's yet another blow to your ego. So the challenge is on. I can't help but see all this as a challenge to your ego.

Perhaps others will not see it this way; but all that you've said is about a high school crush. You are after her, and she comes with a two year-old child. You have yet to outgrow a high-school adolescent-crush; yet you think you're ready to take-on a ready-made family.

You are bordering on delusional, my young friend.

Dating women with children is for those who are mature and experienced. Men who are prepared to take-on marriage and the whole kit and kaboodle. Not starry-eyed dudes who think they have finally found a golden-opportunity and can win the girl of their dreams. You have so much more maturing to do, in my opinion.

You're counting on taking advantage of her vulnerability, seeing as she is alone and rejected. You'll be her knight in shining-armor.

Reading your post, I just saw too much adoration of an ideal, and not enough maturity and preparedness. I see a guy who needs to date single young-women without kids, and needing more experience under his belt; before pursuing very complicated relationships that will include kids.

She said she isn't dating anymore. That means she's dealing with some personal-issues. Maybe that includes some pain and bitterness. She needs healing time. More than likely, she has unfinished business with her baby's daddy.

Let go of that old schoolboy crush, and get your ego under control. She is in the process of reorganization; and focusing on herself and her kid. She has no time for some guy who just wants to prove to himself he can overcome her past rejection; and now that she's down and out, you have a chance.

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A female reader, Youcannotbeserious United Kingdom + , writes (22 February 2018):

Youcannotbeserious agony auntWell, first of all I think you need to give yourself time to get over YOUR break-up. Don't try to persuade her to be your rebound relationship. That really WILL be a big mistake.

The reason friends and family are telling you it is not a good idea to date her is that you are YOUNG. Yes, older couple often have children they bring with them into new relationships but, when you are in your 30s/40s/50s, you EXPECT a new partner to have history which may include children. At your age there are many young ladies your age to choose from who do NOT have a child.

The child is the reason you need to proceed with caution. The last thing she needs is to get attached to you, only for the relationship not to work out and for you to disappear, just like her father did.

That aside, there is nothing to stop you meeting up with this girl and being friends. In time she may change her mind about dating, especially once she realizes what a nice person you are (I am assuming you ARE nice!). You will get chance to get over the break up of your relationship and she will get chance to get to know you without any pressure to date. Don't press her to date. It is not what she wants at the moment. However, don't give up on her changing her mind either if she is so special to you.

Good luck. I hope it works out.

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A female reader, mystiquek Japan + , writes (22 February 2018):

mystiquek agony auntThe lady said no. Take her at her word. I was a single mom at 21 and trust me the last thing you are worrying about if you are a good parent is dating and worrying about some guy. A small child is a FULL TIME job that requires all of your time, all your energy and unless she has wonderful family that help her out, she probably has very little time to herself. I understand that you have a crush on her, but it doesn't mean that she returns your feelings. You are not 16 anymore, so don't act like it. If she wanted to get to know you better, she would have indicated as such. Sometimes dream have to die, OP. To be honest, you don't even really know her and sometimes what we build up in our minds isn't even close what is reality. If you really go to know her, your bubble may burst, she may not be anything like what you imagine her to be. Sorry if the words are harsh, just trying to make you see things for what they are, not what you WANT.

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A reader, anonymous, writes (22 February 2018):

Male Anon, no. She said NO. Do NOT keep asking her for dates or telling her how much you want to be with her. You only asked for her number and she said NO DATING. We need guys to LISTEN to us. Jeez.

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A female reader, Honeypie United States + , writes (22 February 2018):

Honeypie agony auntIs it a bad idea to date a girl with a child?

No. Not really. However is it a HUGE responsibility for her to be raising a child on her own. And what SHE needs might be something you can not give her. Putting her on a pedestal is NOT what she needs. Which is probably what your parents are thinking. Plus, they might not believe YOU are quite ready to "settle" down yet. They might not believe you are mature enough for this.

Is it a bad idea to TRY and date a girl who ISN'T wanting to date?


Just because YOU had a crush on her in HS doesn't mean she owes you squat. And "pretending" to want to be friends might not be an honest approach either. But, IF she is willing ACCEPT that friendship is all she wants. My guess is she is (temporarily - probably) done with dating because of what she went through with one or more boys. She wants to focus on her child, NOT guys.

You need to LISTEN to what she said and respect it.

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A male reader, anonymous, writes (22 February 2018):

Let her know how seriously you want a relationship with her. Now is the best time for you to make your moves. Don’t procrastinate, and don’t give up easily. You only live one life, so at least try your best.

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A female reader, Andie's Thoughts United Kingdom + , writes (22 February 2018):

Andie's Thoughts agony aunt"she adamantly stated that she’s not dating anymore"

"if a girl says she’s through with dating, going out, and being young…should I respect that?" ABSOLUTELY. You should ALWAYS respect what someone says they do and don't want. You're pestering her, otherwise.

"I’m willing to trade my early-mid-twenties to be with her if that’s what it takes" and when you still don't work out? You'd waste years of your life on a crush from your adolescence.

You should absolutely move on. She's said NO. It's not just about dating a single parent; it's you putting your crush over her decision not to date. You can't just spend time with her because you want to ask her out for dates, which is what you'll be thinking of hanging out one-to-one, while she doesn't want dates.

Leave her alone. Move on.

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