Dear Dr. NerdLove,
I´m a recent fan of your website, I believe the direct approach you normally use is excellent for those of us that drift among decisions.
Speaking of which, I hope to receive a piece of advice from you. I’m a 30 years old single man living in Mexico City. I still live in my parents’ house, I have a steady income and a steady job, but I have plenty of difficulties with the socializing and meeting new people areas, especially women.
So far I´ve only had one serious relationship (in my college years, 8 years ago approximately, it lasted a couple years) and a few flings, but nothing serious. The thing is, I have recently resumed my friendship with my longtime high school crush, only to discover that I still have feelings for her (or at least that´s what I believe).
She´s also a 30 year old woman, divorced, with an 8 year old son and a boyfriend/concubine that lives with her at her house. She has financial issues, and she´s also the only income in the house. Her boyfriend is like another child in the household, and of course she´s having problems with her former husband. As I was saying, we have recently resumed contact, we support each other, and I lend her money when she needs it, we talk about life, and I still have feelings for her, I can´t help feeling a strong attraction. Recently we talked about life and love and things like that, and I asked her if she would consider date me if the circumstances were different, she said yes, but it was not a definite answer, it was more of an ambiguous thing.
She also said that she will draw the line, and if her boyfriend doesn’t get a job in the next few months, she will kick him out of the house (which not necessarily means the end of the relationship). Also, I should mention I heard this thing before, and nothing ever happens. He doesn’t want to, or can´t get a job, and she doesn’t kick him out. At the end of the conversation, she offered to introduce me a single friend of her, and that thing caught me off guard.
I don’t know what to think or do in this point. I´m not so naive to think that she´ll realize everything I´m doing for her and eventually run into my arms, that would be simply stupid.
The thing is that I feel this situation is overwhelming, I´m 30, single and still living with my parents. Meanwhile all my friends are either getting married or having babies (or both like my best friend´s case) , the peer pressure is terrible.
I should also mention that I have no problem with her single mom status, I believe I´m mature enough to handle a relationship with a kid involved. Of course, I wouldn’t mention it to my parents immediately, but I believe I´m mature enough to handle the situation if necessary.
I would lend a hand financially speaking if necessary, that means no problem to me.
I don’t know what to do.
Either I come clean and tell her how I feel (with the risk that she won´t talk to me or see me again) or I ignore my feelings for her, then move on and accept the blind date with her friend (as an action that will symbolize my defeat with her and my “moving on” attitude). I don’t want to lose what I have with her right now, but I know that it is simply not enough for me. But then again I prefer a friendship, over not seeing her ever again.
Help me Dr. Nerd Love, you´re my only hope.
Prince Charming To the Rescue
Let’s start with the most immediate of questions: the possibility of a relationship with this friend of yours. This is what I would tell you if she wasn’t your long-term crush and just someone you were starting to flirt with and things were going well.
Don’t do it. This is a train-wreck waiting to happen. It’s already a complicated situation with her being a single mother and you having virtually no dating experience at all. Dating a single parent isn’t something to be entered into lightly; not only does she have her own life to consider, she has to consider what’s best for her child. She will always have obligations and responsibilities that by necessity will take precedence over you. And should things be even remotely serious – as you’re hoping for – you’re not going to just be involved in her life but in her child’s as well. You are, in effect, going to be having to negotiate two relationships for the price of one; this can be tricky under the best of circumstances, and doubly so when you have very little social experience.
And honestly, your hesitancy to tell your parents that you’re dating a single mother is a pretty good sign that you’re aware that this is likely more than you can handle.
The other reason is that her social life is already a mess. She’s in conflict with her ex-husband – who presumably is always going to be a factor in her life – as well as her shiftless, lazy boyfriend. And, let’s face it, she’s not terribly interested in losing him yet; for whatever reason, she has yet to follow through on her threats to kick his ass to the curb. Maybe she loves him more tan she’s exasperated by him, maybe she’s afraid to be alone, maybe she’s prone to bad decisions, maybe they’re locked into some co-depended cycle that just replays itself over and over again… who knows. Regardless of her reasons, this is one giant, heaving mess of bad decisions that you’re trying to insert yourself.
On that score alone, trying to date this woman is a holy-shit-super-bad idea under the best of circumstances. Now let’s take it up to the next level here with the rest of your situation. You’ve had a crush on her for at least 14 years, even with zero contact between the two of you. This in and of itself is a warning sign: you’ve had an especially nasty case of Oneitis. To make things worse, you’re compounding it with White Knight Syndrome, with visions of sweeping in there and taking her away from this life of privation and heartache. Hell, you’re already giving (not lending; you know as well as I do that you’re not going to see that money again) her money on the regular. All of this is a very big sign that you are not equipped to handle this relationship. And let’s face it, you can say that you don’t expect her to notice everything you’re doing for her, but you sure as shit are hoping she will.
Let’s be honest: this is about fulfillment, not about about her as a person.
You’re already somewhat socially isolated. You’ve been feeling the overwhelming pressure to get married and pump out some kids, coupled with your embarrassment at continuing to live with your parents and your generalized anxiety over your difficulties in socializing. Suddenly you high-school crush is back in your life, representing everything you could want: an instant family, the chance to finally achieve an old fantasy and even be the gallant hero, hauling her out of a horrible situation and into a new and glorious life for you! You are more in love with the idea of her and what she represents. I don’t doubt that you’re attracted to her, but she’s much more of an aspirational figure than a real person, and all of those niggling details – her relationship with her ex-husband, her current boyfriend, etc. – are not going to go away. These are all going to be part of her every-day life, even if she liked you back in the first place
But here’s the thing: she’s not into you that way. You’ve already broached the subject of whether she would be interested in dating you if things were different and got a non-committal answer; this is in and of itself an answer. It’s a “no”. Then on top of that, she immediately offers to set you up with a single friend of hers. These are not the actions of a woman who is considering you as a potential boyfriend or husband; this is someone who likes you as a friend and appreciates your emotional (and financial) support, but simply doesn’t return your feelings and is trying not to hurt you.
I don’t mean to shatter your dreams, but this is simply not going to happen. She’s not going to dump her boyfriend any time soon and, even if she does, she’s not going to fly into your arms.
What you need to do right now is work on yourself some. You’ve got a good base to start with; having a steady job and reliable income is important, especially with the way the economy is right now. Spend some time improving your social skills and meeting people. Go through the basics in the archives here; you should also consider reading Succeed Socially, another site I recommend. If living with your parents is something that’s causing you anxiety, then start saving your money and make plans to get your own place. The more you get your life in order, the less pressure you’re going to feel to rush out and try to play catch-up with all of your friends.
Go on that blind date. The more dating experience you have, the better you will do with your future relationships… and you’ll find that your Oneitis will fade as you start to get to know all the new and amazing women out there.
I just recently turned 27, and have yet to have an actual relationship. I often worry that the place I’m currently at in life makes me undateable: I just transferred from a community college to a university, and I still have a couple of years of undergrad to go.
I worry that I’m too old for the women at the university. They are all in their very early 20s, and as such, I feel like I am inherently determined to be creepy and to have made terrible life decisions simply because I’m older than all the “normal” students. (It’s not even just the women in that aspect, I feel like everyone’s eyes are on me because of it.)
Because of my situation, paying for university, while also paying for a car, working at a retail customer service job (even working full-time hours), I have not been able to afford to move out of my parents’ house. (The school is only about 20 miles away so I commute.) It’s not like I’m the stereotypical lazy moocher living in the basement: I do a lot of work around the house, and I keep my space of the house very clean as well. But because of this, I feel like all the women who have already graduated college will not want anything to do with me either, being past the point of tolerating men who are in college and/or do not have real jobs and homes of their own.
I feel like I’m the only one who’s in this position most of the time, and it leaves me feeling rather isolated. Is there hope for me with any demographic? Or should I not even bother trying until I’ve graduated and found a real job and a place of my own?
A couple of things: you’re only five to six years older than the average college student. That’s not an insurmountable – or even terribly unusual – difference in ages. Hell, if you go by the cliched guideline of “half your age + 7”, then you’re firmly within the boundaries of acceptability. When I was in college, there was a wide range of ages – most of my peers were around my age, but there were many, many people in their late 20s, even some in their 40s in class and nobody thought twice about it. Some folks get a later start than others, some get into college late after military service, others were only able to wrangle the finances to go later in life.
The awkwardness you’re feeling? It’s mostly in your head. I say mostly because yes, there will be some judgmental pricks who think that anyone over the age of 25 is ancient and wonder what the fuck you’re doing there. That’s all well and good – they’re assholes, and you wouldn’t want to date them in the first place. They’re doing you a favor by self-selecting out of your dating pool. Pay them no mind because ultimately they’re irrelevant to your life. Being creepy is about behavior, not life circumstance. If you’re not acting like Humbert Humbert around the co-eds and just socialize with them like you would anybody else, then you’ll be fine.
Don’t forget: the economy is still in the crapper. There are lots of people who have to live with their parents even after they feel like they shouldn’t. Hell, all things considered, what you’re doing is pretty damn impressive. You’re paying for school, and a car while working full time in a customer service job? All of that is a testament to your ability to prioritize and get shit done.
Now I’m not saying that it’s going to be easy, but it’s not the hopeless case you’re picturing. Everything is in how you present it. If you’re going to carry yourself as some hyper-developed man-child who can’t hack it in the real world then of course people are going to not respond well. If you present yourself as somebody in a tough situation who’s doing the hard work and making the sacrifices to get out of it? That’s another thing entirely. So you live with your parents: big goddamn deal, that’s a temporary necessity so you can pay for your education. You’re working retail – ok, but not only are you paying for school and a car, you’re showing that you’ve got ambition. You’re not coasting through life in some prolonged pseudo-adolescence, you’re busting your ass to make the most out of yourself. That’s something to be admired. If people can’t respect that, then fuck them, you’re better off without them.
I do think you’ll find in trying to date amongst your fellow students is trying to find someone you can relate to. When I was in my late 20s, I had a hard time dating anyone younger than 24; past that, we were simply at such different points in our lives and had different priorities and cultural reference points that it really wasn’t going to work out beyond the very short term. But there will be people who are more mature and who aren’t living the life of the stereotypical college student; those will be the ones you have the most compatibility with. There will also be plenty of women outside of your classmates; consider meeting up with some of them.
Just remember that other people are going to take their cues from you. If you come across as confident and that it’s no big deal, then they’ll respond the same way.