Love, Lindsay

'How Do I Overcome The Age Boundary And Date Women In The Same Stage Of Life As Me?'

All your relationship questions — answered right here, right now.

Lindsay here, A Plus's resident relationship guru/columnist. While I may not know everything, I do know a lil something about love and our seemingly endless pursuit of it. Having written dozens of A Plus articles about dating, relationships, and sex, I'm ready and willing to investigate all of your romantically-inclined questions (submit here!) — because I've asked them myself. What I hope to bring to A Plus's readers is a sex-positive, body-positive, and most importantly, you-positive perspective on modern love. Consider Love, Lindsay your digital Cupid. 


Dear Lindsay,

I need your advice. I'm a guy in my mid-20s in New York City, and I feel as though I'm at a great disadvantage because of my age. I've found that younger women are either in college or dating guys who are older than me. Older women, of course, don't seem to be interested in dating me either.

Almost all of the women I date are in college or are uninterested (or both). At this point, I would consider it a minor miracle if I found a woman at the same place in life as myself (single, mid-20s, gainfully employed) who was actually interested in me.

How do I overcome the age boundary and start dating women who are in the same place in life as me?



Hi Ben,

First, it's important to note that New York City is swimming with potential people to date, but you, my dear Aquaman, are casting too wide a net. I know that might sound like the opposite advice for someone who is having difficulty finding someone interested in him, but that may be because you're looking in the wrong places. 

Of course, while avoiding the wrong places is simple enough, finding the right places may be easier said than done, as Julia Bekker with Hunting Maven, a matchmaker and dating coach, is quick to note. "I understand how you may feel like you're stuck in a gray zone," she says. "Most people your age are not established with their careers yet, still trying to figure life out and not taking dating so seriously. Being ready for a relationship with no options must feel polarizing, however I don't think the issue here is about the age as much as you think." 

I not only agree with her, but think this is hidden key to you unlocking your full dating potential. "You said you would be surprised to find a woman your age who would want to date you. Why is that? Sounds to me like you are lacking confidence which i'm guessing is a big part of the problem," Bekker adds. "... Everyone has insecurities, you have to embrace who you are and value yourself. I'm sure you have a lot to offer, you must date with that belief and attitude as well. Know your worth and others will see it too."

Try taking an honest look at your dating history to assess how you've projected yourself to potential love interests in the past. Because, as Becker says, confidence is key. But that confidence should come from embracing who you are and what you want. 

"The problem is less about your age and more about your mindset and probably the women you are choosing as well as your confidence level and approach," Bekker says. "... The truth is you are at an ideal age to date, and have fun with it, and you have plenty of time to work on yourself and meet the right person, don't sweat it."  She suggests taking the "I need this to turn into a relationship" pressure off yourself when you go on a date and go into it without any expectations other than to just have fun while getting to know another person. 

This is important because when people enter into a relationship for the sake of being in relationship, it often ends up being unsatisfying, short-lived, and with the wrong person. That said, I do think it's OK for someone to approach dating with the set goal of finding a relationship, but I believe that's different than making the choice to be in one just because you're worried that if you don't jump into one right now in your mid-20s, you'll have missed your chance. Trust me, you won't. When it comes to finding the right person, I believe it's never too late. 

When you're not going on dates with other people, take the time to date yourself. What I mean by that is setting aside some time, perhaps once a week, to answer the questions you'd want a love interest to answer. What do you value in a relationship? What lessons have you learned from past romantic interactions — successful and unsuccessful, big and small? Do you fall into any dating patterns that have been setting yourself up for failure?  From there, what past lessons can you apply to each new dating situation? How has your romantic history informed the person you are now? Answer these questions truthfully, and then let those answers guide the way you approach and interact with potential love interests.

That's the beginning of working on yourself, and to continue that from the inside out, Bekker suggests picking up some hobbies, engaging in your passions, doing whatever it is you love to do. "That's not only good for your soul but you can meet like-minded women that way too!" she explains. One way to do this is checking out for groups getting together to do these kind of activities. While you may not meet someone you're romantically interested in immediately, you'll most likely expand your friend group, which can lead to new social situations and a whole new kind of romantic encounters.

And let us not forget the power of dating apps. If you're on one (or a couple — go for it), Bekker advises having "good, recent pictures representing who you are and showcasing your personality." Going back to being mindful of how you project yourself to potential dates, take advantage of each dating app's bio option to be honest about who you are and what you want. "You can also say that you aren't looking for just a hookup to attract more relationship-minded matches," Bekker concludes. 

Not everyone will be responsive to someone so straightforward, but that's exactly my point. When you're dating from a specific perspective, you should only be trying to attract people who share that perspective. The right person — whoever and wherever she is, and trust us, she is out there — will not only be at the same place in their life as you are, but will want to head in the same direction with you. 

Love, Lindsay 

Cover image via Unsplash


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