Why Am I Still Single? (10 Questions to Ask Yourself)

Valentine’s Day is now behind us and for some people, they celebrated V-day with their significant other— whether that was a romantic night out at an upscale restaurant or a night in, eating McDonalds, and watching Netflix, they got to spend the day with their special someone.

Others spent the day with friends and family — whether that’s catching up over brunch or having a night out — they got to spend the day with the people that matter most to them.

And the rest, well, they spent the day like most singles do… alone. 

Although there is nothing wrong with celebrating Valentine’s day with some well deserved R&R, some singles still ask themselves the same old question:

Some singles grow frustrated at the idea that their forever person is not here, whether they’re on dating apps, using a professional matchmaker, going out to bars, or relying on fate to meet their special someone. They live their everyday lives seeing people around them getting boo’d up or hop on social media to see couples all smiley and giddy; it can get on their last nerves.

Some singles even come up with ridiculous explanations as to why they’re still single! Some of these include: “The good ones are taken,” “All gay men just want sex,” “They’re not at my caliber,” “They don’t make enough money,” “I’m still getting over my ex,” and the list goes on.

Believe it or not: YOU may be the real reason why you’re still single. Now before you come after my wig and tell me that’s not the case, have you reflected and asked yourself ALL 10 questions below? 

As a Certified Matchmaker for Gay Men, I found that a lot of the single gay men I worked with don’t take it upon themselves to self-reflect and affirm themselves when it comes to their past dating journey: They just want to get right to the matching. 

Below are 10 questions I have listed that made some of the singles I’ve worked with take a step back and rethink their single status:

What do I mean by “high/low expectations”? When it comes to dating, some singles feel that a high caliber result is required for them to feel satisfied, while others feel they deserve the bare minimum and set a low bar.

Regardless of how high or low the expectations, if those expectations are not met, most likely, singles become disinterested in the person in front of them and count themselves out of the running.

You can’t have expectations. Why? Because expectations lead to a one way ticket to failure. Your special person is not going to satisfy all of the expectations on your must-have list and that’s a reality you need to face.

You may surprise yourself when it comes to your expectations. It’s no surprise to me if the preferences or dealbreakers of some of my matchmaking clients are way too specific or not high-quality enough. That’s why they hire me for my services to assess and decode their personality and match requirements.

If you’re having a casual conversation with a friend or family member and even they’re telling you that you may be way too picky or you’re not making an effort when it comes to your characteristics, you may have to adjust your dating mindset.

The answer to that question may come as a no-brainer for some, but for others, it’s a question that’s worth evaluation.

When you enter the dating market, it’s important to ask yourself, “What’s the outcome that I want out of this? I have to identify the reason why I am dating and for what purpose.”

Some people decide that they are ready to seek out a life partner, but don’t even bother to look at the bigger picture. As a trained love professional, the bigger picture goes back to my four main pillars of long-term commitment:

• Are you looking for the intent of marriage or partnership?
• Do you want or don’t want children?
• Are you both on the same path religiously/spiritually?
• Are you both sexually compatible in the bedroom?

If you’re not looking at the bigger picture, the chances of you taking dating seriously is little to none, so it may be worth reflecting on yourself to take action instead of dating passively.

For my date coaching clients specifically, it’s always worth mentioning their dating history. But more than that, whether they’re on the dating apps or not, I always ask my clientele what type of single is reaching out to them.

The gay app dating world is a challenging place to meet people. We now live in an era where we not only constantly swipe, but we evaluate potential matches based on physical attractiveness and whether they’re open to sexual advances on first encounter.

It’s important to ask yourself this question as it may reflect on how you’re presenting yourself on a profile or in real life. If you’re coming across as someone who is looking for sexual intercourse, you may have to alter your profile to present yourself as the real deal rather than a one-nighter.

I can understand that you may be a busy professional who doesn’t have the time to waste on swiping, but for other singles, it never hurts to give the apps a try with purpose.

It may sound contradictory coming from a professional gay matchmaker, but believe me when I say some dating apps are supposed to be used so you can delete them after a period of time for the right reason.

I’ve met couples in today’s modern world who have met on dating apps and are still going strong to this day. Although I’ve mentioned on occasion that some app users maliciously sabotage their profiles, there are men who use the dating apps in search of someone with values and beliefs that align with their own.

Whether you’re working with a professional matchmaker or waiting for life to take its course, if you want to increase your dating chances, it’s always worth taking advantage of the dating apps. You’ll never know what happens unless you try!

Dating fatigue is real. The longer you’ve been single, the more frustrated you can become. I would know… I was single for four years straight during my college years.

When you become frustrated in your dating journey, you start to lose hope in the idea of finding your long-term partner. Some people may even lower their standards just so they can meet more people, only to find that the person in front of them is not to their caliber, thus frustrating their drive and motivation even more.

No matter how long you’ve been single, the key things you need to remember when it comes to dating is to have resilience and patience. Dating is a process, and for some, it will take months to years to find the person they’re meant to be with and that’s OK. It’s part of the process. If dating were easy, everyone would be in a relationship, but that’s not the case.

As long as you affirm to yourself that you’re worthy of a partner, they will come your way, but until then, you must stay resilient and be patient. The lack of drive and motivation will only cause you more harm.

While question number two addressed the issue of singles not taking advantage of their dating journey, question number six addresses an equally concerning issue.

If you’re bringing up serious topics right away on the first date, the likelihood that you are scaring your date away is highly probable.

Think of the first date as an initial compatibility date because that’s what it really is. You really just want to have a fun night out on the first date and get to know someone new. If you bring up the need of having kids, ready to get married by tomorrow, or even have a political debate, it can cause turmoil on your date.

When you’re on the first date, always remind yourself that you’ve just met this person. You don’t know this person inside and out. You can’t tell yourself that you’re falling in love with this person. It could just be infatuation.

Before you can claim someone as your mate, it’s important to date first and enjoy the process of getting to know someone. 

This question highly impacts individuals who either just got out of a serious relationship or can’t let go of their first special someone.

The sad reality is that for some newly single people, your first loves are not going to be your forever person, but rather, the person in that moment. Whether the relationship ended negatively, platonically, or ended due to life events, getting over your first love can take  longer depending on how long the relationship lasted.

You may have been capable of love then, but it takes time for you to get back on your feet again. Your past may be the reason why you may still be single. You may have to heal first before you can get back out there, and that’s totally fine.

In addition to your love life, you still have everyday life to deal with.

That includes your career, finances, social life, hobbies, interests, short-term commitments, and long-term goals. The fact of the matter is you may have other commitments on your plate that you feel are more important than love.

If you can’t prioritize your life, how in the heck can you balance loving someone else? As a love expert, I strongly advise that you straighten out your life priorities so you can balance your love priorities.

If you’re struggling when it comes to finances or need to focus your full attention on work or school, love is not in your cards at this time. Trying to balance everything on one plate will only cause the plate to overflow. 

Before you ask yourself question number 10 on this list, you should ask yourself this question.

The real reason why you may still be single could be because you may not actually be long-term, committed material. And that’s not coming from a place of mischief or arrogance, but rather a more contextual dating placement mindset:

• Some singles date to find a long-term, committed partnership.
• Then there are singles who date in a more serial style.
• Others date for a sexual outcome.

There are even singles who date to network and meet other like-minded singles, with no specific outcome in mind.

Singles, in general, date differently. You have to date with purpose and authenticity to separate yourself from those who date for other reasons.

Not only that, you need to ask yourself if you’re dateable material. Why should someone date you? What do you have that other single candidates may not have? This can be a number of factors:

• You may be more financially secure than others
• You may have personality traits that others find attractive
• You have hobbies and interests similar to your match
• You align with your match’s religious background or spirituality
• You may be ready to settle down just like your match

Why are you date-able? If you can’t come up with a list of reasons, you may not be long-term, dateable material.

This is probably the number one question you should ask yourself. It’s a question that most singles fail to ask themselves before entering the dating world.

When it comes to dating and relationships, you are sacrificing your personal time and energy for someone else. But more than that, you are opening yourself up and letting yourself become vulnerable to someone you’re not required to be vulnerable to. Are you emotionally ready for the outcome?

Most singles in a new relationship are in the honeymoon phase, an early part of a couple’s relationship where everything seems carefree and happy. When something doesn’t go your way, are you emotionally intelligent enough to assess the situation?

When the big-picture questions come about, whether that’s marriage, kids, or moving in together, are you ready to have that talk? Are you willing to compromise or make sacrifices for your person?

Some singles are not emotionally ready for that. And if you’re not ready for that, it all goes back to questions seven, eight, and nine. This causes your partner to doubt what your goals and intentions are for your relationship. 

When entering the dating scene in search of a relationship, be ready for anything — positive, neutral, and negative. You need to be in a mindset where you are ready for any outcome, and it can be a lot to handle emotionally.

Why are you still single? There’s a lot of reasons really. Did any of these questions make you take a step back and question yourself? It may be time to self-reflect and come up with a plan to make a change in your relationship status.