Instead of telling your old work crush that you have always had feelings for him, start building some rapport with him first on the online dating site.

Being that he is your old work crush, you already have an advantage that other women who may try to contact him don’t.

He is familiar with you and thereby will be more willing to actually engage in a conversation with you.

Being that he is your old work crush, he may want to talk to you about old times at the workplace that you both worked at.

That is where he knows you from and thereby, he will feel most comfortable in engaging in that kind of a conversation at the start.

You should be patient in your approach.

Avoid expressing your feelings for him too soon.

A good way that you can build rapport with him at this stage is to be just as reminiscent as he is about your old workplace.

Be positive in your conversation.

Try to focus on the positive elements about the old workplace.

If you were to fall into the temptation of being negative in what you say about your old workplace, he may start looking at you as a negative person.

This never leaves a good first impression.

So, even if you may not have enjoyed working at this old workplace, you should avoid talking negatively about it.

Your old work crush is on an online dating site for a reason.

After breaking the ice in your first few exchanges where you are both most likely going to be talking about your old workplace, you should ask your old work crush what he is looking for on the online dating site.

This is very essential.

Though your old work crush is on an online dating site, this doesn’t necessarily mean that they are looking for the same kind of relationship that you are.

Hence, though you know that you have always had feelings for him, he may not necessarily be at a stage in his life where he is open to having feelings for anyone.

You should not assume that he is on an online dating site for the same reasons that you are.

Doing this could totally put you at a disadvantage if you were to be too premature in telling him that you have always had feelings for him, only to discover that he isn’t even seeking a serious relationship at this time.

When he tells you what he is looking for on the online dating site, you will have an idea of where to go from there.

If he isn’t looking for what you are looking for, it is best not to tell him that you have always had feelings for him.

This would only put you in a really awkward position.

You would be putting him under a degree of pressure to feel the same way that you do.

This is not a position that you should put him in nor yourself.

Even if he were to try to woo you upon gaining this knowledge, it wouldn’t come from a place of sincerity.

If his heart is not there at this stage in his life, it just isn’t.

On the flip side, if you discover that he is looking for the same kind of relationship that you are, this would be your opportunity to start building some real rapport with him.

Don’t get all excited and tell him that you have always had feelings for him right away.

Instead, proceed to build rapport with him by flirting with him and mixing that up with asking him substantive questions about himself and his life.

Find commonalities in the pastimes that he describes to you and show enthusiasm when you do.

Continue flirting with him from time to time and keep your conversations with him energetic.

If he has continued communicating with you consistently for some time and has enthusiastically been responding to your flirts, there is a good chance that he is really liking you.

By this stage, you would have built enough rapport with him to tell him that you have always had feelings for him.