The Approach

There are many people I’ve communicated with who have no idea how to express and pursue romantic or sexual interest in someone else, at least if it doesn’t involve an app.

So, I thought I’d cover a few basics.

I want to make it very clear from the start that none of this is about imposing on someone against their consent.

On the flip side, it isn’t assault or harassment to approach someone who has expressed no interest in you yet, as long as you do it respectfully and gently, and back off if they decline. (You might want to avoid approaching anyone in your workplace, though.)

This IS about how to discern if someone else could be interested in you this way and letting them know you are interested them in this way. I can’t write for every set of customs on the planet, such as “arranged marriages” and elaborate rituals, and this essay assumes you are able and willing to act on mutual consent between you and the person you’re trying to approach.

This is mostly written with younger adults in mind, but much of it can be applied to adults of any age, especially if it’s been a long time since you’ve successfully looked for a partner in-person.

Approaching someone requires vulnerability on your part. You will be expressing (more) interest in them, and they might reject you, or at least decline your invitations. Thus it has been for generations. “Nothing ventured, nothing gained.” Nothing “works” for, or on, “everyone.” People are diverse. So be flexible, adapt, and never impose on someone who has indicated they’re not interested.

Preparing

What are you looking for? A hookup/one night stand? A potential spouse? Something in the very wide spectrum between? Or is your answer to that question “Any of the above; it depends on the person?”

What you’re looking for helps to guide you on how you prepare.

What do you have to offer? Be honest with yourself. Is there anything about you that would interest potential lovers? Maybe you’re fun to hang out with. Maybe you’re a good conversationalist. Maybe you have a sexy body. Maybe you’re a good companion in general. Maybe you can touch your forehead with your tongue. Maybe you’re going to be a wealthy businessperson. Maybe you’re saving an endangered species.

If you don’t think you have much to offer, maybe you don’t. Or maybe you’re being too hard in yourself. But if you are lacking, there are ways to grow into someone who has more to offer. All some people want is someone who’ll listen to them, make them laugh, and touch them tenderly. 

How’s your hygiene and grooming? Except for rare fetishists, potential lovers want someone who is clean, doesn’t smell bad, and takes care of themselves. Clean hands and fingernails and a clean mouth (as in brushed teeth and good breath) are usually musts.

How do you present yourself to others? Does the way you dress indicate you care how you look? What’s your style? Don’t try to look like someone you’re not, but do look good for whatever your style is. That can range from a nice business suit to biker leather, a sundress to a business skirt.

You have self-control - usually. Most people have experiences and feelings that can overwhelm them from time to time, but if you’re looking for love, or sex, or sex AND love, behaving in a desperate, fearful, or out of control way won’t get you anywhere. “Losing control” is only good in the heat of passionate sex - sometimes. Not in getting to there.

Approaching Someone You Don’t Know Well

Approaching complete strangers or acquaintances, or neighbors you don’t know well is different than approaching someone you already know, which I will discuss below, after I discuss this.

The easiest way to begin is to ask questions that express interest it them. If they’re wearing, carrying, or doing anything that indicates their interest in something, asking about it can be one of the safest ways to start. If nothing else, you can ask them for their opinions on something nearby you’re about to try/buy/do, ask them for directions, or even ask them if you know them from somewhere or have met them before.

Asking them appropriate questions allows them to reveal more about themselves to you. In general, the more they’re willing to talk with you, the better. Also, their tone of voice and body language can give you indications. Are they smiling at you? Looking at you? Or are they putting up metaphorical walls, being curt and distant? If they are smiling at you and looking at you in a way that indicates they like what they see, that’s a good sign. Ask follow-up questions that show you’re listening to them and gets them talking about things that interest them or they are eager to share.

Offer compliments. These shouldn’t be crude. “Nice ass!” is usually going to be inappropriate, unless you’re at a farm as they’re showing off their donkey. Something like, “I like your hair,” or “Nice shoes,” or “Your eyes are gorgeous,” or “I like the way you kicked that mugger in the groin and threw him down the stairs.” Compliments can also be about something they said. “That sounds fascinating! I’d like to hear more about that.”

Flirt. Flirting usually consists of smiling, what you’re doing with your eyes, your overall body language, your tone of voice, and being playful with your compliments and whatever else you say. In so far as they welcome them, flirting can involve light, gentle touches such as on their arm or shoulder.

Set up a date. If everything above is going well, meaning they’ve received your flirting well and are flirting back, or at least they’re not breaking out a spray can full of mace, go ahead and ask for their phone number, and if you can, a date. Some people insist on being pursued rather than pursuing; if you’re one of them, offering your number and leaving it up to them to text or call is OK.

Make it easy for them. If you are OK doing the, or some, pursuing, suggest what you want to do, where, and when. For example:

“Will you join me for coffee or tea at Donna’s Tea Factory, tomorrow afternoon at 3? My treat.”

They might agree. Or decline. Or they might make a counter-suggestion, such as “How about Gary’s Frozen Yogurt at 8pm?”

That’s fine. There are people out there who tell you not to be flexible at all. Ignore that. Your goal is to set up a time and place for you two to begin to get to know each other better. Someone who comes back with an offer of a different time, place, or activity wants to spend time with you. Otherwise, they simply would have declined. By the way, dates don’t have to cost much. Meeting at a park for a nice walk and sitting on a bench can be most of the date; but keep in mind that most people aren’t their best on an empty stomach or with low blood sugar.

Another essay will address what to do on dates, but starting at step 5 on this page and adapting it to your situation can help.

That all assumes you have someone in front of you you’re interested in. If you don’t, go where you’re likely to find people you might want to date. Bookstores used to be great for that, because you could see what they were reading and that might reinforce your interest. Or not. Such bookstores are getting harder to find. If you’re attending college, a trade school, or any other adult educational institution, going where other students gather can help. At any age, getting involved in an activity that indicates common interests, such as a charity or another nonprofit, or some local civic, hobby, or sports club can be a way to do that. Of course there are also bars and night clubs, if that’s your thing.  

Approaching Someone You Know Well

If there is someone you know well, and you want to add a romantic and/or sexual bond with them, attempting to initiate that may have some differences from approaching someone you don’t know well.

A benefit is that you already know each other. A potential hindrance is that for some people, if a romantic or sexual bond wasn’t explored with them before, they might have placed you in their mind into a nonsexual, nonromantic category, and changing that can extremely difficult.

It might help to understand why it has been a nonsexual, nonromantic relationship up until now. There are so many possibilities. Some of them include:

• Availability - at least one of you wasn’t available, whether due to existing commitments, geographic distance, mental or physical health issues, or more

• Professional connection - you were previously coworkers or boss/employee, one of you did some work for the other, you were educator and student, etc.

• Personal growth or transformation - at least one of you has recently figured out your priorities, matured, gained sobriety, achieved some stability, accepted the truth about your gender/sexuality/relationship needs, started to see the other as an attractive romantic/sexual person, gained the courage to be vulnerable, etc.

• Customs or taboos - you now realize that the disapproval of some strangers, especially dead strangers, shouldn’t prevent you from adding bonds with this person 

Don’t assume they are available just because you don’t know of any current partners, nor should you assume they’re unavailable because they do have current partners (although if their response to your approach is to tell you they have a partner, that’s usually a nice way of declining your offer, if it’s not part of a discussion about nonmonogamy).

Starting at step 4 on this page and adapting it to your situation might help.

Also, adapting much of what was written above about approaching strangers can work in getting this person you know to see you as a potential romantic/sexual partner and signal your interest in them as such.

Ask them open-ended questions to get them talking about romantic and/or sexual relationships. Ask for their opinions, thoughts, desires, preferences, experiences; whatever will get them talking. Need a starting point? Ask them about their dating life, or their thoughts about someone or something in the news - like a famous couple, or about other people you know, or a fictional situation you watched or read about, or mention a dream you had (even if you have to make it up). If things are going well enough, you can ask them questions that relate to your history and existing connection with them, even if you don’t clearly make it about the two of you. For example, “Do think it’s OK for former coworkers to date?” If they say yes, you can ask them if they’d be willing to date a former coworker. If they say yes, you might be able to ask them for a date.

Offer compliments. An advantage in offering compliments to someone you know well is that your compliments can be specific to the things they care most about. Some compliments should be more of the romantic or physical nature than you’ve offered them before, complimenting their appearance, for example.

Flirt. Flirting with this person should include much more physicality than with someone you barely know. More touches as you pass by them; leading them by the hand or otherwise holding their hand(s), more hugs, longer and tighter hugs, perhaps with drifting hands; kisses, more kisses, more suggestive kisses; even sitting on their lap or inviting them to sit on yours or next to you, depending on the situation.

Get them alone/Set up a date. Things aren’t going to get very far unless you can get them alone, or unless whoever else is present is supportive of you two getting together. This may involve going out on dates but, depending on the situation, might involve dates at home. Especially if it still hasn’t been established to them you are interested in them romantically and/or sexually, setting up regular, recurring dates might help. For example, suggest getting together regularly to watch movies, or play tennis, or go for walks, or share coffee, or play games/cards, or whatever, whether weekly or daily or whatever makes sense that you’ll both enjoy.

Discussion is essential. Because you’re trying to add additional bonds to an existing relationship, sooner or later you two will have to discuss what’s happening. It may feel weird or awkward, especially to them, even more so if it goes against customs or taboos. They may need reassurance that you’re not acting on a mere whim, or confused, and that this is truly what you want. Be prepared for them to express hesitations based on the prior bonds you have shared; your sincerity and thorough assurance can clear away those hesitations if they are able to reciprocate your feelings. If they can’t reciprocate your feelings, they may cling to the hesitations to soften saying “no” to you.

Again, never impose yourself on anyone against their consent.

A subsequent essay will examine dating behaviors.

As always, you’re welcome to comment below.

Reach out to Keith to privately discuss the topics in this essay more. He can be emailed at fullmarriageequality at protonmail dot com, sent a message on Wire messaging app at fullmarriageequality, messaged on Bluesky at @marriage-equality, and X at @FullMEquality.