Set up people you already know well.
Don't bother setting up people you don't know well. If you try matching up a good friend with an acquaintance who you really don’t know much about, there is a risk that things can go wrong beyond the two not having any chemistry. That acquaintance might turn out to be an unpleasant person or even dangerous. Be sure you really know the two people involved before attempting to coordinate a romantic connection.
Consider the consequences if the match doesn’t work out.
Think about what might happen if things don’t go smoothly. Suppose they do go on a date but have a miserable time and never want to see each other again. That might mean that you cannot invite the both to the same social gatherings, such as cookouts at your place. Keep this in mind when considering setting up two people who have the potential to run into one another again after the date. If the two friends are coworkers, even if they work in different departments or separate buildings, it might be best not to play matchmaker. If things end badly between them, there is still the potential that they could run into one another in the workplace. Another thing to keep in mind is how your friendship with both parties might be affected. If things don’t work out between them, you could find yourself caught in the middle should they choose to gossip about one another to you. You might even be asked to choose sides. If things do not work out, offer each friend a simple apology. You can say something like, “I’m sorry things didn’t work out.” Then, avoid bringing up the topic again. Only discuss the situation if the other person brings it up first.
Choose friends who have something in common.
Your two friends will need to have something to talk about during the date you're trying to set up. When they have shared interests, it will be easier for them to connect with one another. Plus, shared interests tend to lead to more meaningful connections. At the very least, you want them to enjoy their time together even if they don’t make a romantic connection. One method for opening up one friend to the idea of being introduced to another friend is to say something like, “Have I ever mentioned my friend Rick before? I was just realizing that the two of you have both been to Spain.” Avoid setting up friends who could potentially clash over major lifestyle differences. For instance, if you know your guy friend can’t wait to find someone to marry and have children with but your female friend doesn’t plan to have children and prefers to take it slow in her relationships, that might not be a wise match. Don't match up 2 friends just because they're both single.
Tell your friends about your intentions.
Let your friends know that you’d like to introduce them to someone because you think they’d hit it off. It’s best not to be sneaky when trying to bring two people together. Both parties should be open to meeting. Otherwise, things could get awkward if you thrust them together unexpectedly, which might squash any chance of them developing a romantic relationship. When speaking with each friend, be sure to highlight the positives about the other person. Try saying something along the lines of, “I have this friend Jill who is really great at cooking. She’s funny too. I think you’d like her. Maybe I can introduce you some time, if that’s alright with you.”
Introduce your friends subtly.
Focus on making them feel comfortable. Talking about how they’d make a great couple when they’ve only just met could make them both uncomfortable. Additionally, making a quick introduction and then walking away might leave them both feeling awkward with nothing to say to one another. Likewise, avoid putting them in a situation in which they are the only two single people at a gathering. When first introducing them, let them get to know each other a bit before pushing them together as a couple. When one friend approaches while you’re talking to the other friend, introduce them by name. Then try saying something like, “You know, Mia enjoys gardening and has a green thumb just like you Joe.” Now your two newly introduced friends can strike up a conversation about their shared interest in gardening.
Arrange a casual meeting.
A great way to get your two friends to spend some time around each other is to invite them to a casual gathering. With you there, you can help focus the conversation on a topic you know is of interest to both of them. Plus, you can keep the conversation going in moments of awkward silence so that neither of them feels overly uncomfortable. Invite your two friends out for appetizers or drinks. Organize a weekend cookout or host a small party at your place and invite both friends. Plan a mutually liked activity, such as hiking or mini golf, and invite both of your friends to join you. If you are in a relationship, suggest a double date with you and your partner accompanied by the two friends you wish to set up.
Avoid forcing a love match.
Don't push it if neither of your friends are interested. They might not hit it off immediately, but perhaps they will down the road. Pushing things too much in the beginning could sabotage any possibility of them making a connection in the future. Likewise, pushing your two friends into a dating situation they just aren’t interested in might damage their friendship with you.
Limit how much you follow up with them.
You'll probably be curious about how the date went, but don't overstep any boundaries. Your friends will likely anticipate you following up with a few questions. However, just because you introduced them doesn’t mean they have to share every detail of their date with you. Avoid pressuring your friends to tell you everything. Do not interrupt your two friends while they’re out on a date alone. Avoid texting to find out how things are going until you are sure the date is over. Waiting until the next day to follow up is best. When you do follow up, try asking something simple like, “How did things go?”
Refrain from interfering.
It might be tempting to continue helping the match along, but don't do it. Once you’ve introduced them and they’ve made the decision to get to know each other better, your work is done. Unless one of them has specifically asked you to remain involved by mentioning something specific to their date or by organizing another outing, you should stay out of it. Your friends don’t need your help coordinating every step of their potential relationship. Plus, they might get annoyed by your constant interference, which could cause problems in your friendships with both parties.
Set aside your personal feelings.
It can be exciting when you match two friends together who end up making a love connection. Things don’t always work out, though. It’s possible that the two people you attempt to set up romantically won’t have any chemistry. There’s nothing you can do about that and you shouldn’t take it personally. If your intentions were good and you genuinely thought your two friends would hit it off but don’t, just accept it and move on.
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