Dear Sara: I never really have trouble attracting dates to be honest — I am a former model (although never did much professional work but suffice to say, I am conventionally attractive/fit) and also a lawyer to boot. I’ve been told men may find me intimidating by females and some men have admitted this although others say I appear friendly and they don’t think I’m intimidating. I’m not sure.
My personality has changed quite a bit over the years in that I have become more social and friendly, a bit more socially normal let’s say (I used to be quite introverted and socially awkward I think) and it’s a bit difficult to describe my personality. I appear very different around different people. I know I have some insecurities because I was quite sheltered in my youth/upbringing; hardly saw any movies referenced in pop culture or TV shows while a teen (therefore hugely catching up now although I was never much into movies to begin with… maybe due to being single so long..never had weekly movie nights with a bf, etc.) and these insecurities still play on me at times. I also grew up quite poor so I don’t connect on the same level with many wealthy attorneys who golf and go skiing in their free time. In truth, I feel like a misfit between two or three worlds and I have no idea how to meet people somewhat similar to me. I am a bit picky in that I want someone I find physically attractive (which is tough enough in itself) but I tend to privilege intelligence and personality much more. Whenever I DO meet someone who tends to measure up though, I feel hugely undeserving. This is also quite rare — I have been single for years. I usually lie and just say two years — realistically since 2014, so 3 years. I also sometimes just make things up to appear less odd/abnormal which has blown up in my face before.
I do know I need to be myself but I am a newish lawyer with little financial means at the moment due to a lot of school debt; focusing on building my career (which is well paying so if I do well hopefully it will pay off…!!) and can’t do the many things most of my acquaintances can like travel, ski, engage in arts and self discovery overseas because they can afford it. I am trying to discover my passions but my #1 passion is to travel and I haven’t been able to do it due to lack of funds. I also subconsciously feel like wealthy men may write me off when I say I haven’t been able to travel yet without knowing the circumstances of why. They simply see me as less sophisticated and may move on. I don’t know.
I DO know objectively from the outside, I look like a great catch because I’m constantly told I’m beautiful/gorgeous and even still offered modeling gigs at times despite my advanced age for it. Why I can’t find a relationship I don’t know. I’m getting to the point where I believe I may be hopeless as I’ve never had a relationship last longer than a year, and even that was with a guy I wasn’t even into just to prove to myself I could have one. I recently started seeing a counselor but even she thinks I’m successful and nothing is wrong with me so I’m not sure it’s much help. Any advice appreciated for where I can look to find like-minded guys who won’t just dismiss me or do I have to improve myself to get those guys? – L
Dear L: In your letter, you gave me many examples of things that could possibly be preventing you from finding a relationship: You’re introverted, not earning a lot, unable to travel. You’re not into movies, and you miss many pop culture references. Your upbringing means you don’t feel like you fit in with your professional colleagues. You worry that you might be too awkward, too intimidating, or too outside of the mainstream.
You are also beautiful, hard-working, and successful. You’re a person who was able to transcend a disadvantaged upbringing and become a lawyer.
Here’s what you sound like to me: A person. You have strengths. You have weaknesses. You have things you’re confident about, and things you’re insecure about. In other words, you’re pretty much like all the rest of us, regardless of whether we are in a couple or not.
I can’t tell you a specific reason why you haven’t found your person yet—it was a question I mulled myself when I was your age (and beyond!). My sense is that you simply need to meet the person who appreciates your strengths and doesn’t mind your frailties, and for whom you can do the same. I think that’s all any of us really do.
So instead of worrying about being too intimidating, focus on finding someone who appreciates an independent woman. Instead of worrying that you don’t yet have the money to go skiing or play golf, focus on finding someone who has the depth to be interested in you, not what you can afford at the moment.
I get that that is much easier to say than to do. And I’m not against self-improvement, but if the goal is to get a guy currently writing you off because you’re not rich or deferential enough … well, I don’t think anything you can do in that regard would be an improvement. If you want to make yourself happier, calmer and more peaceful, by all means do that work. But do it for it’s own sake, not because you’re trying to prove yourself worthy of a certain kind of guy.
As far as meeting like-minded men goes, it’s possible that pursuing the things you enjoy (and can afford) for their own sake will help you find a good match. But that’s not guaranteed, of course. You might need a more direct approach. Consider telling trusted friends and family members that you would like to meet someone and ask if they have any thoughts. After they inform you about the existence of internet dating—gee, thanks!—they might actually come up with a decent idea or two. Even if they don’t know of any men to fix you up with, they might think to invite you to join them for a cocktail party or other event. Or they might notice that their kickboxing class is 80 percent men. Or, somewhere down the road, when they’re talking to a guy at a conference they’ll think hmmmm. People are so busy and caught up in their own stuff that they might think to do this on their own, so try and get some agents in the field.
Not everyone will be a good candidate for this. Some people will use your query as an excuse to dissect your personality and tell you what’s wrong with you. So if that happens, politely tell them that you’ve been doing your own internal work and change the subject—ask them about their kitchen renovations, or their upcoming camping trip, or whatever their favorite topic is.
In other words, focus on finding leads to meet the right guy, rather than a personality overhaul to attract the wrong one.