Ways To Gently Ask A Guy Where You Stand Without Scaring Him Off

The “Where is this going?” conversation. Bringing it up can be really tricky. At best, it can make you feel awkward and vulnerable. At worst, you suspect that you might not hear the response that you want to, but you feel the need to ask anyway.

Marlene Kerubo
The Savanna Post
6 min readOct 21, 2022

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Man and Woman Talking at the Table.

How do I ask this guy where I stand, in a way that will get an honest answer, but without coming across as too pushy/accusatory?

POV: You met him about 4 months ago and he seemed really into you. You went on a few dates etc, you asked him at the time what he was looking for and see said he really liked you, wants to get to know you better and see where it goes. That was a few months ago, and since then you’ve basically just got the impression he’s leading you on. You cut him out your life for a few weeks and ignore his texts/messages but he won you round (yes you feel a bit of a fool) and you start texting loads again.

He’s gone back to the way he was, basically telling you he really likes you, wants to see you etc but being really vague when it comes to actually organising anything concrete. You said to him he could just be honest if he didn’t want to see you but he was all ‘I really do want to see you asap’. You’re 99% sure he is just leading you on, but you just want him to give you an honest answer, even if it is that he isn’t interested, at least that way you will have closure and will be able to move on without wondering what could have been. You just need him to say it.

What should you say to him/ask to get a clear upfront answer, but without sounding pushy or accusatory about the way he’s been acting? It’s not always easy to know how to go about this, though, so here are some steps & tips to follow.

1. Avoid Labeling Too Soon.

When you are caught up in fantasies of happily ever after, it is easy to forget that you haven’t been dating too long. For a reality check, take a look at your calendar. If it hasn’t been at least three months of dating, then you need to scale back your worries.

Men sometimes need a little more time to decide if they are truly interested, and asking him how he feels after the second date leaves him feeling confused. While it’s best to avoid putting a label on your relationship in the early months of dating, you can still gain insight into how he feels by letting him know that you like him.

Most likely, he’ll at least give some type of reinforcement that lets you know that he is interested in deepening the romance.

2. Make Sure You Want to Know.

This is one conversation that can truly change a relationship. Before you ask, prepare yourself for receiving an answer that you don’t want to hear. Hopefully, all goes well, and you will end your conversation with a kiss.

However, it is possible that he’ll say he’s just playing the field, and you will need to make a big decision. Keep in mind that continuing the relationship is also an option if you feel he’s worth waiting for and there might be a future down the road.

3. Don’t Do It via Text!

Not only do you risk it coming out wrong because you won’t be able to control the tone, but you might end up frustrated if he takes a bit of time to get back to you. He might also be busy with something else and unable to give you his undivided attention, which will make it worse. Save this convo for real life.

4. Don’t Go In Too Seriously.

If you’re feeling nervous about having the talk, it’s easy to just blurt out what’s on your mind, but try to take a deep breath first. There are few sentences that come with as much baggage as ‘we need to talk’ in modern dating.

If they’re already a bit gun-shy about defining the relationship, hearing that will only make them more anxious. You’ll get better results by saying something like ‘Hey, can we talk about where we see things going between us?

Having a gentle start to the conversation can help ensure that you’re both in a good frame of mind to talk about the serious stuff.

5. Be Clear About Your Feelings.

If you’re trying to figure out where this is going, it’s not the time to downplay how you feel about this person. I always recommend that you give to get. Be vulnerable to see vulnerable. Be open to see open. If you want to get closer to someone tell them something that very few, if any, other people know. That means sharing how you feel about this person, even if it’s hard to admit how much you like them. Be clear about what they mean to you, because it’s important to find out if you’re on the same page.

6. Be Direct And Don’t Bail Out.

If someone you’re seeing tries to avoid this conversation, make it clear that you want to get at least a sense of what they’re looking for — and don’t let them brush you off or make you feel like you’re being pushy.

My main tip is to keep it casual and keep it direct. Don’t be afraid to ask. And, if they’re avoidant, either gently push for an answer — or take their avoidance as the answer. If they can’t have the conversation, then they’re almost certainly not looking for anything serious.

7. Try To Make It A Back-And-Forth Conversation.

You don’t need to set everything in stone right away — see if you can start having a back-and-forth conversation. The quickest way to push somebody to one side of the fence is to force them to choose.

If you start the conversation by making the ‘talk’ a list of demands, you might very well force them to make the easiest decision — to leave. The focus should be on sharing your thoughts, wants, and needs, listening to theirs, and determining how to move forward in a way that you’re both happy with. If you can open up a conversation, there’s more of a chance you’ll find common ground.

8. Have A Plan If It Doesn’t Go The Way You Want.

When you get into this conversation, you need to be prepared for the fact that you might not get the answer you want — and then you’ll have to respond accordingly.

When you get a less than stellar response, I advise people to basically tell them, ‘If you see a future call me, if not, no worries, I’ll be moving on.’ And, I would seriously move on fast, unless someone totally does a 360 like immediately and apologizes for being so callous and says, ‘You caught me off guard and I really do see a future with you. You mean a lot to me.’

Remember That It’s Better To Know Where They’re At.

Finally, remember that it’s better to have this conversation and move on if you have to than avoid it and waste your time. Ultimately, the conversation will go better if you can have a “que sera, sera” attitude, so try to take a deep breath and remember it’s for the best.

It’s much better to know the answer directly than beat around the bush and end up misled, confused, and hurt. Amen to that. If it wasn’t meant to be, that’s OK.

Initiating the, “Where is this going?” conversation isn’t easy — and it’s tempting to bail out halfway through, especially if the other person acts like you’re being unreasonable. But stay strong and know that you’re asking the right question — and you deserve an answer.

The Take-Away.

Keeping communication open is important in every relationship. While the urge to avoid being hurt is strong, you must find out where your relationship stands. Just be honest and direct, and your guy will let you know how he feels so that you can decide whether to stay or move on.

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Marlene Kerubo
The Savanna Post

I am a bold lady and fiercely independent. I love exploring the world, but my heart is always in home.