Gay Dating Steps

Gay Dating

3 Important Gay Dating Steps to Follow for Success

Mason Glenn

Written by: Mason Glenn

Mason Glenn

Mason has had a long career in the matchmaking industry and has spent his time helping high-caliber clientele in Los Angeles select eligible matches. He specializes in working with gay men. Mason has the ability to read people based on their personality traits, relationship history, and biological thinking process. His training, personal experience in the field, and intuition play a key role in his making of lasting love connections. Currently, Mason is an acclaimed published author and is in the process of strengthening his career in content and brand strategy. His latest book, "Getting Ahead of the Gayme: Man First, Gay Second," can be purchased through Amazon, iBooks, or Google Play, and is available at select major book retailers.

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Edited by: Lillian Castro

Lillian Castro

Lillian Guevara-Castro brings more than 30 years of journalism experience to ensure DatingAdvice articles have been edited for overall clarity, accuracy, and reader engagement. She has worked at The Atlanta Journal and Constitution, The Gwinnett Daily News, and The Gainesville Sun covering lifestyle topics.

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It doesn’t matter if you’re gay, bi, queer, or just horny, we’ve all been on dates that felt a little lackluster. A meh first date that doesn’t get you excited for a second date. Too often, gay singles report having more awkward dating experiences than dates that truly woo us. So, why are so many dates so dull?

Here are some of my explanations for why some dates are “just OK” as well as my top steps for making a gay man’s romantic connections more successful, meaning they lead to more dates or even a long-term relationship.

1. Communicate, Communicate, Communicate!

I’ve mentioned communication a lot during my dating coaching sessions with clients as well as in most of my previous advice articles, but it really is pivotal in terms of creating momentum and sustaining excitement within any relationship, including a gay relationship.

We always want to feel like our potential partner is thinking about us, even if we don’t hear from him. This is especially true in the dating app game when we have so many “banked” options.

I can’t tell you how many guys I would start a conversation with on a dating app, and, by day three, if I didn’t get a response, I wiped them from my prospects. I wanted to know that they took dating seriously, and it wasn’t just a hobby of theirs that they get to it whenever they are bored. I think having so many options when it comes to dating apps can dilute our excitement to meet just one good person at a time.

Photo of gay couple talking

Men need to get better at discussing their feelings, good and bad.

Once you find that right man or compatible person, it’s important to establish a nice cadence of conversation. Hopefully, that rhythm yields a date within five to seven days of when you guys first started chatting.

Take the time to establish that in-person chemistry and compatibility, and remember it’s still important to keep things interesting even a few dates in. Checking in on how his day is going and coming up with another good date idea is a great example of keeping the relationship going strong.

As a gay dating coach, I don’t often hear that a man is over communicating with his partner. I hear more stories from clients about the guys who “waited three days to text me back because he said he was busy.” Do better, men!

2. Determine Early On If You Have Similar Friends and Lifestyles

Looking at your potential partner’s friend circle and lifestyle are two ways to determine long-term compatibility. I always tell my coaching clients that it’s important to like a partner’s friends, and vice versa. This has proven to be true because a lot of times, as a professional matchmaker, I hear clients say “I want to date a guy who I can just leave in a room of friends, and he can be comfortable.”

Not everyone gets along, but, as long as there is a mutual understanding and respect, your relationship will flourish. In most of my longer term relationships, a majority of my friends genuinely liked my partner. For the relationships that only lasted less than three months, well, I’m sure you can guess the reason why.

Your friends are a reflection of your character, and vice versa. I have such a vast hodgepodge of friends of different ages and with different professions and personalities, and I want my ideal partner to be a chameleon of sorts. Look at your friends to identify the words you would use to describe them and decide if it’s important to you that a romantic partner fits in.

Photo of group of friends

It makes a big difference if friends and a potential partner get along.

I’ve also always been a huge advocate of my clients having similar lifestyles with their partners. Typically, you’ll be able to cue into a man’s lifestyle based on their photos and what they mention in their dating profiles if you are dating online.

If you don’t have this wealth of information, one of my favorite questions to ask on first dates — and to be asked on first dates — is “What are you passionate about?” The first two to three things he mentions are things he thinks about or does a lot. If someone asked me that question, I would say fitness, cooking, and helping people. So, if a date cringes at the thought of taking a hike or working out with me, having many major dietary restrictions, and/or volunteering with me early on a Saturday morning, we’d never get along.

You need to know what you’re passionate about, and you need to determine how important these passions are to you. Life is about compromise, but too much compromise can just be demoralizing, depending on the priority you assign to those passions.

Be a participator, though, and give it a good thorough shot even if something is out of your scope of expertise or interest. Your other half should be able to recognize and appreciate that.

3. See If You Two Can Handle Life’s Ups and Downs

Let’s say things have been going really well with you and your new partner, and there have been talks about being exclusive, making a commitment, maybe even finally moving in with one another. The timing of this is case by case, but I would say, on average, this stage happens around one year of dating. If you’re ready, that’s great. You will learn a lot about each other and grow closer.

However, if you aren’t ready, you aren’t ready. That’s OK. A good way to practice living together and determine how you two will handle it is to travel together a lot.

Photo of busy airport

You learn a lot about when you see how a partner handles stressful situations.

I recommend you go on at least three big trips before shacking up. This is a great relationship lesson to see how the both of you are when you’re out of your comfort zone and how you both deal with stress together. There also can be the budgeting of time and money on trips, so that can be a way to see how you may manage life together.

In dating profiles, I see a lot of “someone who doesn’t take himself too seriously” verbiage. But I wonder how that dynamic changes when someone has made a poor choice on timing, and now the both of you may miss your flight and not have that perfect tropical vacation you wanted. These types of situations will give you a true glimpse into what it may be like living with this individual. It will be an adjustment, but hopefully not a painful one.

Most Importantly, Be Gracious and Respectful to One Another

The commonality I see in strong relationships is gratitude. Your partner should always feel respected and cherished by you, and you should always feel respected and cherished in return. A successful relationship goes through several stages, and not all of them are easy, but each partner should hold onto those feelings of love and admiration that brought them together.

To be a good partner, you need to put in some effort to make your time together special and show gratitude for your date. Some acts of gratitude are obvious (gifts, compliments, favors, etc.), while some are unspoken, like doing his dishes at the end of a romantic meal at home.

One amazing dating tool is identifying your Love Languages to learn how you both perceive, receive, and give love. Learning to think like your partner — which is a more selfless mindset — can allow the relationship to organically grow into something special. Good luck out there!

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