Men's Dating

Your Crush is Finally Single! Here’s How to Make Your Move

Suzanne Oshima

Written by: Suzanne Oshima

Suzanne Oshima

Suzanne Oshima is a matchmaker and dating coach at Dream Bachelor & Bachelorette and is the founder of Single in Stilettos. She has been seen on Bravo, The Today Show, Good Afternoon America, Inside Edition, BBC Radio, Men’s Health, Glamour and much more.

Edited by: Lillian Castro

Lillian Castro

Lillian Guevara-Castro brings more than 30 years of journalism experience to ensure DatingAdvice articles and reports have been edited for overall clarity, accuracy, and reader engagement.

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When the girl you’ve been secretly in love with for months or years breaks up with her long-term boyfriend, you’re excited because this is your chance to jump in to rescue and date her.

Hold on…not so fast!

While I know this may seem like the perfect opportunity for you, it’s not!

No matter who broke up with who, breaking up is hard on both people involved.

It’s the end of a relationship where they had a real connection and commitment to each other, so it’s a real loss for both parties.

The worst thing she can do is date right away.

If she does, all she will be doing is trying to distract herself from what she’s truly feeling, which is sadness and a sense of loss.

If you date her too soon, you could end up being the “rebound guy.” This could lead to a short-term relationship instead of a long-term relationship, which is what you ultimately want.

Now you’re probably wondering, “Well how long should I wait? Should I wait a month or three months to six months?”


“It’s important to connect to

her on an emotional level.”

There isn’t a standard right answer.

It’s really based on when it seems like she’s healed and isn’t still thinking about her ex all the time.

Once she shows signs she’s ready to move on, then it’s time to make your move and ask her out.

When you do, it’s important for you to be confident and just tell her you want to surprise her on Saturday night and take her out.

Women like men who are confident, decisive and take the lead.

Now here’s the key: Do not take her out for the run-of-the-mill dinner or drinks date. Why? Because any guy can do that!

You want to set yourself apart from the rest of the guys, especially her ex. So surprise her and take her out to something she had mentioned in the past that she truly loves.

Trust me, you’ll win big points for remembering something she told you about herself a long time ago.

Show her a really great time.

It’s important to connect to her on an emotional level because that’s how women fall in love.

Be confident and use your sense of humor to make her laugh. Share things about yourself she may not know and get to know her in a more personal way.

And, of course, don’t forget to be a total gentleman on the date so it makes her look at you in a completely different light than she did before.

Trust me, if you do all the right things on your first date, she’ll have such a great time that she won’t even remember the name of her ex.

Fellas, how do you go about dating a woman who just got out of a serious relationship? Do you wait, or do you jump right in?

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