General Dating Questions/So.. What am I doing?


Ali! Hello.  ^.^

So, here's the thing.  I'm 25 years old and a bit of a "nerd".  I love ALL genres of movies+music, helping people with whatever, and playing video games. =-P
I'll try to keep the "backstory" pretty quick so I don't take forever in this message.

5 years ago in December 2009 I was living with my mother in a house- and was working in a Meat Department in a grocery store until May 2012. I left the store, and she moved a couple hours away to my hometown. So I moved with my sister in the same city and got a new job. I worked there for about 2 months until October 2012, before I decided I wanted to move back to my "hometown" as well about the time I was 23.  So here's where Now comes into effect.

I'm currently living with my mom in a 1 bedroom apartment. I spent the first while of 2013 looking for a job, and finally got one just after I turned 24. Worked for a couple months, has a "bad ending relationship" with a coworker & just left instead of trying to work things out. So I spent another couple months looking for a job. I got another job & left that middle of 2013. Found a new job in October 2013. My 4'th week, I became ill and missed a day. Despite calling in 2 hours ahead of time, the next day when I went in for my shift- I was let go.

So in January 2014 I found another job requiring On-Job-Training (via Work-One), and my first week there was just stupid and I hardly got ANY training.  Basically my first day in work I got told what to do, showed for about 1 minute, and was thrown to the wolves for the rest of the day until he came by a few hours later, and told me to do something else for the rest of the day. Only took about 1-2 hours max to do what I was told to do both times. So I spent half the day over-working the same areas because no-one would tell me what to do. So I left that job.  To me, OJT is actually TRAINING. Getting checked up on every so often. Not learning for 1 minute, then fending for yourself for 3 hours, Move areas & fend for yourself 3 hours. Go to lunch then fend for yourself for 5 hours.  

Now start of March 2014- I've applied tons of places, had a couple interviews, but don't hear anything back and I haven't worked for about 1 month. Thursday morning I got up to go with mom to do laundry so, and go out and apply at another job I hear is hiring. So I drop her off at laundrymat, apply at the job, and go back to laundrymat. I go inside with my Nintendo DS and clothes still have another 30-45 min. Mom is talking to someone at table we're at so I put my headphones on and play a game to stall time for another 30 minutes without disrupting anyone. Laundry is done and I help mom fold clothes and turns out, the lady mom was talking to at Laundrymat was my cousin's friend and neighbor before my cousin moved a few months ago *Who also lived in the same apartment complex*. So mom invites her to go see my cousin & her kids the next day (Saturday).  I guess they left earlier because when I woke up mom was just getting home. She told me that her & cousin's friend (Still a neighbor in the same apartment complex a few buildings down) were talking in the car to see my cousin. Mom told me she finds me cute as well as asking if I currently had a girlfriend (Which I don't).  

Mom said she asked her age- and she said 30 (Which is NO problem with me, because I get along 3x better with people 30+ years of age better, than I do 27 or younger.  She also has 2 daughters around I'd say 5-9 each. I woke up today and as I was checking my E.Mail- mom told me that that lady sent me a friend request on Facebook as well. So I added her of course and that was that.

So now here's where the QUESTION finally comes in! I saw her get on earlier today and post a comment to someone and nothing else. I didn't get message or anything. Based off her profile, she don't seem to get on FB too often and I get on about twice a day. Granted they're basically "neighbors" I never see them outside either *Of course this Winter is terrible anyways, where I live*.

What exactly should I do? I mean as far as I really know it's usually a guy that first makes contact or tries getting to know a female. So do you think I should wait an extra day or 2 and see if I get a message? Should I be the one to send her some type of message? Any ideas what it should say?  Like I said earlier- right now I'm pretty much a bum until I get another job and get income. Hopefully soon! So she surely knows about that little detail already.  This is just a really interesting way to actually "meet" someone. To find out through a parent that someone implied they may like you. It's just unique, and don't have any idea what I should do in this particular situation.  

Any advice is greatly appreciated.  Have a great day!

Hi Matt,
Thanks for taking the time to write. From what you've told me, it sounds like your lack of employment may be hurting your confidence. With regard to a job, I urge you to really think about what you want to do for a living and come up with a plan to achieve your goals. Is there some additional education or skills training you can do? At this point, you want to find a job that will provide you with opportunities to learn and develop. If you find that the "on the job" training feels inadequate the first day, I would advise that you be more proactive, follow up with your manager or other coworkers and ask for continued guidance. I realize that your question was not specifically related to work, but you spent so much time describing that part of your life when writing that it seems as though you may have been looking for guidance there.

This winter has been a brutal one and it would be difficult to bump into a neighbor outdoors, and will probably continue to present a challenge, at least for the next several weeks. From what you've told me, Matt, this woman has been fairly straight-forward in her approach. She's already stated interest, she friended you on Facebook and now she's probably waiting to hear from you, to determine if there's any interest on your part. I suggest you be the one to message her first, just saying "hi" or something along those lines. If you're feeling especially forward, perhaps you could ask if she'd like to grab a coffee or a drink one evening. Realize this might be a challenge, though, since she has two young children. So planning will be key.

How do you feel about the fact that she has two young children, Matt? Are you up for the challenge of dating a single mother? You noted that the age difference isn't a problem, which is great. But really think about what you want from a relationship long-term before heading down this path. If you're just looking to  have fun, your expectations for a relationship may be different from a woman who is almost 10 years older and who has two children. Just take a moment to consider what you want from life before jumping into a situation that could create considerable awkwardness with your cousin, your mom and your neighbors should things not work out. I'm not saying that the two of you shouldn't get together to at least see if there's any chemistry, but if there is, you may want to take things slow and set clear expectations to ensure the friendship/relationship terms are clear.

I hope I answered your question, Matt. I wish you luck finding a new job and hope its one that leads to more opportunities and professional development. I also wish you luck with your neighbor - she's already extended the invitation, so don't be shy, just reach out and introduce yourself via FB. Ask her about her interests and see if you have anything in common.

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I can answer questions related to "the chase"--whether to be patient or more assertive. I can answer questions regarding break-ups and moving on. I can answer questions related to flirting and meeting new people as well as how to inspire them to call you.


I have much personal experience as well as often play the role of matchmaker and advice-giver with many of my friends. I took several classes related to gender relations in college, giving me a solid perspective on communication between couples and what it means.

My writing has appeared on a website and various anthologies.

Graduated with a BA from Villanova University.

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