[Anonymous]

Ok so ill try to keep this as short as possible but here’s my story. The last 8 months have been the most torturous of my life because of this huge perdicament I’m in, as every possible decision seems to be the wrong one.

Im 23 years old. Back in the fall I met a cute girl at my school, but as soon as I found out that not only she was six years older than me but also a single mom, I imediately ruled out any possible relationship with her other then just being friends. However, for the first few weeks of knowing her, she gave me every possible sign that she likes me, like puting her single motherhood on hold to party and hang out with me. All of my friends told me that she wants me, so I considered the possibility. The icing on the cake happened when she practicly asked me to let her come with me and my friends to Detroit to party for a weekend. (Detroit is about a 3 hour drive from my Canadian home). Remember, just 3 weeks prior to this, she was a total stranger. Everyone told me to make a move on her that weekend, as she seemed to give me more obvious signs that I had the green light while in Detroit, but I shyed away, WORST DECISION EVER!!!!!!!!!

When I arrived home after that weekend, I completely broke down, because at that moment not only did my feelings for her become strong, but I realised that I misssed out on the obvious oportunity to seal the deal with her. Ever since that weekend, she hasn’t been the same person towards me. After partying with her every second day the first few weeks I knew her, we partied together just once in the past 8 months. I feel like I blew the best oportunity!! Eight months later, I still desperately want a relationship with her. My problem is, I’m worried that if she rejects me, she might want to distance herself away from me, and if I lose her as a friend, Ill be twice as devestated, as every hallway I walk down at school will remind me of the fun we had together these past 2 semesters. I know this sounds pathetic, but its real.

There are still some things that make me think she still likes me, the fact that a couple months ago the two of us watched a movie at her place, and I sat right up close to her, an inch away from touching her, but she didn’t complain or feel unconfortable. In fact after she left to go to the restroom, she sat right back down in the same spot, right up close to me, when she didn’t have to. When the movie ended, she still didn’t move and we talked right up close to each other. But once again, I shyed away from making a move because im afraid of risking the friendship and furthering my misery. However, the obvious thing that gives me doubt is the fact that shes so much older then me, plus the fact that shes a mother to a three year old. She also said to me a few times, “so many guys think I like them, when I’m really just a very friendly person.”

Anyway, I went on long enough, I think you get the jist of it. I thank you very much for taking the time to help me out. I desperately want to put this problem to bed once and for all, without risk of furthering my depression.

Cheers

[April Masini, your AskApril]

Is it worth the risk? You tell me: You’ve waited eight months to write me, all the while tortured because you want to date her, but don’t want to risk losing her friendship. I’d say that your being tortured all that time is DEFINITELY worth the risk of losing her friendship.

Dating well is like running a business. You have to take risks sometimes. The worst case scenario is that you lose her friendship, but it doesn’t sound to me like her friendship is enough for you. You’re keeping that friendship with her because you’re holding out hope that she may want to date you. This isn’t real friendship. This is a guy not asking a girl out because he’s scared of being rejected, so absolve yourself of any of your thinking that uses her friendship with you as an excuse to keep acting frightened. Your real problem is fear of rejection.

Please understand that rejection is part of dating and it’s part of life. The upside of rejection — and this is a HUGE upside — is that if she does reject you, then you know exactly where you stand with her and you can move on and find someone who wants you and stop wasting EIGHT MONTHS on someone who may or may not. If you get a rejection, the sting will go away and then you’ll move on and give yourself the opportunity for happiness again. If you don’t ask her out, you’re going to stay tortured always wondering, as you have been, if, if, if, if… 😕

Please get and read my book, Date Out of Your League, at this link: [url]https://www.askapril.com/relationship-dating-advice/date-out-of-your-league.html[/url]. It’s a quick download and a reasonable $14.95 and it will give you LOADS of confidence and tips on how to ask her out and what to do on the date to make a good date an amazing date. This purchase is LOW risk. 😆

So that’s my general advice, but….if the real reason you’re not asking her out is because you don’t want to date a single mother or that you don’t want to be responsible down the line for being with a single mother, then make yourself clear on that point. The worst thing you can do in a relationship is to self-delude. Dating a single mother is very different from dating a single woman with no kids. That said, you can be upfront with her that you’re just in this for fun and not a long term commitment, at which point it’s her responsibility to proceed in her own best interest. Six years difference in age isn’t necessarily a problem. And dating a woman with a child isn’t necessarily a problem. Unless it’s not what you want for yourself. If you just want sex or fun or both, without a future, just be upfront because she may want the same. But again, this involves risk — and you’re going to have to put your big boy pants on and start taking some risks in life. Everyone does. Everyone has wins and losses. Welcome to the club! 😀

I hope that helps — let me know how it goes. And join me on Facebook — I’d love to have you there. Here’s the link for AskApril.com on Facebook. It’s free and fun and easy! 😀
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