How to Attract an Older Man at Work

Co-authored by Erika Kaplan and Hannah Madden

Last Updated: May 28, 2022

If there’s an older guy at work you just can’t take your eyes off of, you might be wondering how to catch his attention. Attracting an older man is a little bit different than a younger man, but fortunately, it’s not too difficult to do! Keep reading to learn how you can make him notice you at work and (hopefully) land the guy of your dreams.

This article is based on an interview with our professional dating coach and matchmaker, Erika Kaplan Check out the full interview here.

1

Connect with him about your shared interests.

You might share a hobby or something you like to do in your off-time. Get to know him a little bit more and ask him what he does for fun. If there’s anything you two have in common, bond over it and chat about it at work.^{[1]
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Expert Source

Erika Kaplan
Dating Coach
Expert Interview. 1 October 2020.}
- Common interests are a great segue to hanging out outside of work, too. For instance, if you both like sports, you might ask him to go see the baseball game with you next weekend.
- If you both love getting out into nature, invite him to go on a hike with you.

2

Show off your maturity.

Older guys appreciate it when people around them can hold their own. Take on responsibility at work, and don’t complain about your workload or your to-do list. Accept challenges and face them head-on, and try not to blame others for your mistakes.^{[2]
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Expert Source

Erika Kaplan
Dating Coach
Expert Interview. 1 October 2020.}
- Not only will this help you attract a man at work, but it can also help you do better at your job. It’s a win-win!

3

Maintain your independence.

Older men appreciate someone who won’t rely on them for everything. While it’s fine to lean on friends and family every now and then, show the guy that you like just how independent you are. Take care of things on your own and try to make your own decisions about everything around you.^{[3]
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Expert Source

Erika Kaplan
Dating Coach
Expert Interview. 1 October 2020.}
- For instance, you might tell him a story of how your car broke down on the highway. Tell him how you called a tow truck and diagnosed the problem yourself instead of waiting around for someone to come and help you.

4

Exude confidence.

Keep your head held high and your shoulders back. Speak calmly and clearly, and don’t let anyone talk over you. At work, you can ask for things clearly and confidently without beating around the bush. The more confident you are, the more attractive you’ll appear.^{[4]
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Expert Source

Erika Kaplan
Dating Coach
Expert Interview. 1 October 2020.}
- If you aren’t a naturally confident person, that’s okay! The phrase “fake it until you make it” really works—if you aren’t confident now, just act like you are.

5

Smile around him.

If you see him around the office, give him a grin. Smiling is a great way to show someone that you’re attracted to them. Even if you can’t stop to chat, a quick smile lets him know that you’re happy to see him and you’re looking forward to talking to him later.^{[5]
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- You could even give him a little wave if you spot him across the office.

6

Make eye contact with him.

If you see him in the office, try to catch his eye. In meetings or when you walk past him, hold his gaze and give him a small smile. Eye contact lets him know that you’re really seeing him and that you might be attracted to him. Plus, this is an easy way to flirt at work that isn’t super obvious.^{[6]
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- If he holds your gaze and makes eye contact with you, it’s a good sign!

7

Take him out to lunch.

Spend time with him outside of work, even if it’s brief. Ask him if you can take him out to lunch, then go grab a bite to eat together. He’ll probably appreciate you making the first move, and you two can chat without the prying eyes of coworkers nearby.^{[7]
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- Plus, paying for his lunch shows him that you’re interested in him, not just his money. That’s a common fear for older guys, especially when someone younger is hitting on them.

8

Create an inside joke together.

Pick up on something funny that happened at work. When you see him again, remind him about the incident and have a little laugh about it. When you create a joke that’s just for you two, it brings you closer together and can deepen your attraction.^{[8]
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- For example, you might say, “Remember what Jerry said in that meeting yesterday?”

9

Ask him for advice.

Call upon his life experience to give you some tips. Guys in general love feeling like you need them. If you’re having a problem at work or in your personal life, sit down with him and ask for his opinion. He’ll feel like you value him as a person, and it’s a nice way for you two to bond.^{[9]
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- For instance, you might ask, “I’m having trouble deciding if I should go back to school or not. If you were me, what would you do?”

10

Try not to draw attention to his age.

It could make him feel creepy or uncomfortable. If you two are chatting about childhood memories, don’t make a big deal about the age gap in between you two. Keep your tone neutral, and if he asks, say you weren’t even thinking about it.^{[10]
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- You could also say something like, “Honestly, I haven’t even noticed how many years there are in between us. You’re just so easy to talk to, I don’t even think about it.”