When the Matchmaking Urge Strikes: Tips for Bringing Your Single Friends Together

Remember the days when your best friend would pass you a note that said "John's cute - can you find out if he likes me?" You'd mull over it for a moment, then scrawl another note, tear it carefully from your binder, and pass it to John. If you were lucky, the teacher didn't snatch it up somewhere along the way.

Just as the grown-up world of work is usually much tougher than not getting caught passing notes in biology class, playing matchmaker once your school days are long behind you is usually a bit more complicated.

Yet somehow, some of us just can't seem to resist the urge, especially when we're part of a couple ourselves.

Maybe it's like that old Seinfeld episode, where George really wants Jerry to date his fiance's friend. The cynics say married folk want everyone else to be hitched too, because misery loves company.

But most likely, you actually want your friends to be as happy as you are. You're relieved that your days of awkward first dates, anxiously awaiting phone calls, avoiding jerks in bars or scouring online dating sites are a thing of the past. Love looks and feels good on you, and you want your friends to experience the same happiness.

So, instead of looking at the people you meet as potential dating opportunities for yourself, you start checking them out for your buddies. Your boyfriend's best friend is such a nice guy, and handsome too. Your cousin would love him if she got to know him. That new guy in your IT department at work is a sweetheart. You bet he'd really like the girl who lives next door to you. And not that you're always looking out for number one, but wouldn't it be nice if she had a guy of her own so she'd stop coming over and asking your husband to help with her household repairs?

Whether your reasons are altruistic or you're just trying to get your guy's friend hitched so he stops dragging your mate out to the bars twice a week, the matchmaking bug just might strike.

But remember, this isn't high school anymore. Your efforts might result in a new friendship, a great dating experience, or even a long-lasting relationship. Or they could end up a disaster that has repercussions for your relationships with all involved. You know the story. You and your husband decide to introduce your close girlfriend from work with his college buddy. They go out a few times, and then she decides he doesn't have enough ambition or he goes back to the girlfriend he never really got over. It doesn't end well, and the next thing you know planning gatherings at your house is a nightmare. She won't come if he and the ex are invited, or your husband says "let me know if you're inviting that snotty girl from work, so I can warn Joe."

Instead of creating a match made in heaven, you've just added complications to your own social life.

That doesn't mean we should totally avoid helping our single friends with the dating game. Technology has changed the way singles hook up, but many relationships still begin with an introduction from a mutual friend. Introducing your single friends can lead to lifelong love or just a good time for two people you care about. Besides, it can be fun.

So, how do you play Cupid without putting your own relationships in a potentially awkward situation? Is it possible to bring two people you think might be right for each other together without putting them in an awkward situation?

The answer to both questions is yes, if you play matchmaker without playing matchmaker. Get your friends, co-workers, cousins, or neighbors together without them knowing you've got love's arrow secretly stashed in your bow, or at least without putting them on the spot.

Before you start playing Cupid:

Even the most casual and unobtrusive matchmaker takes the time to make sure the ingredients she's trying to combine aren't oil and water. Before you decide to throw your workout buddy and your boyfriend's single softball team member together, get your facts:

What Does Each Person Want Out of Dating?

If they're both longing for a serious relationship, fine. If they're both truly enjoying playing the field and want to keep it that way for a while, that's great too. But if she's tired of the dating game and constantly checking her biological clock, and he just got out of a long relationship and wants to be free for the foreseeable future, then chances are they'll just end up giving each other a headache.

Do Their Lifestyles Seem Similar?

They're really nice, sweet, funny and cute. They're really good friends to both you and your significant other. But will they get along with each other as well as they do with you?

A bit of "opposites" attract is fine. If she's a martini bar and sailing girl, and he's a beer-swilling football fanatic, they still might find common ground and even entertain each other with their different lives. But if he's a chain smoker and she's a rabid anti-smoker who stops on street corners to break stranger's lit cigarettes, then give it up. If she likes to get out and have a few drinks on the weekend and alcohol makes him uncomfortable, put the matchmaking notion aside.

Looks Do Matter

Yes, I know. It's what's inside a person that counts. If he just got to know her, he'd see how beautiful she is. She never ever dates guys shorter than her, but he's perfect in every other way, so she should make an exception this time. Maybe you're right. But if you know that one of your friends always goes for a certain physical type, and your other friend is a far from that type as you can get, why set yourself and them up for failure?

So They've Got Potential. To Keep From Screwing It Up, Avoid These Scenarios at All Costs

They seem to have a lot in common. Their dating goals are somewhat similar. And physically, they're both the type you see the other one checking out on the street. This match definitely has potential.

To keep from dousing the fire before it even gets lit, avoid setting up the following scenarios:

The Blind Date

Talk about pressure. Going on a first date is awkward enough. Going on a date with someone you've never met is even worse. Add on the pressure of both of them knowing you're waiting for phone calls with all the details, and you've just put them on a desert island with no food or shelter and told them you'll be back to pick them up in a week. You're going to walk back in to something ugly.

Sometimes blind dates do work. Two outgoing, adventurous types might even enjoy it. But why take the chance, when there are so many other ways to get them together?

The Couples Outing

This one is almost as bad as the blind date. You're trying to be a bit sneaky. So instead of arranging a date, you invite them out to dinner and a movie with you, your boyfriend, and two other couples.

On the surface, everything seems innocent. But if they're at all sensitive, your single friends will feel the pressure. You might as well hold up a sign that says "look, you two. You're out with a bunch of happily coupled people. It's us, and you. But take heart. You're not the only one here all by yourself. He is too, see. Go ahead, hold hands, exchange phone numbers, steal a smooch. You can do it."

No one likes to feel put on the spot. Even if they're interested, the pressure of the situation will most likely keep them from acting on it. And if one of them is not interested, he or she will just end up feeling like a heel.

Carefree, Easy and Fun is the Way to Go

You don't need blind dates or couple-type outings to get your friends together. Instead, try planning group activities or outings that aren't exactly date-like in nature, but offer up a lot of fun anyway. Throw your friends into a scenario where there's lots to do, and see what happens. Either they'll like one another and hit it off on their own, or they won't. If they don't everyone can have a great day anyway, and no one feels put on the spot.

Springtime offers a ton of ways to pull together your single friends. Here are just a few ideas:

- Have a cookout to show off your significant other's mad grilling skills and all the new things you've done with your backyard.

- Get everyone together to go to a baseball game. Hot dogs, beer, a sunny day and the home team can take the edge off of just about anything.

- Have an impromptu Saturday or Sunday afternoon softball or volleyball game at the local park or in your backyard.

- Suggest that a group meet for a hike, a fishing trip or a combination of both.

- Get a crew together for a night of board or card games at your place....

In general, you want to plan activities according to the following tips:

- Keep your group relatively small, but include enough people that it feels more like a hodgepodge of friends from different areas of your life coming together than a matchmaking design.

- Have plenty going on. Your friends will be more comfortable and likely to observe and get to know each other a bit if they don't feel forced into awkward, stilted conversation. Games, sports, good food, the great outdoors, and lots of easy laughter are all natural ways of pulling people together.

- Remember that a few drinks can loosen people up and make them feel comfortable. Too many drinks will inevitably lead one of them thinking the other is a drunken idiot.

- Make sure you choose activities that paint your friends in their best light. If she's so bad at softball that she's made excuses to avoid the company team for ten years, don't expect her to jump into a backyard game. And if she does, expect her to be so nervous about her performance that the last thing on her mind is how cute he looks in those jeans. Have a volleyball game instead. If he's the type who starts throwing dice around and swearing when he's on the losing end of a board game, consider playing cards instead.

- Spend some time making sure the twosome you have in mind are introduced and know a bit about each other. Encourage conversation. Mention that they're both raging CSI fans while you're serving them drinks. Drop the fact that they were both English majors in college while you're showing off your newly remodeled basement. But don't make it too obvious.

Don't Have Time to Throw A Party?

So you don't have time to pull together a cookout or a day trip so that Jane from your book club and John from your husband's office can meet? You'd like to lend a helping hand, but the kids and the job and all the yard work you've got slated for the next month just don't leave much time left over?

Take heart. There are still ways you can get them together without throwing them into a blind date. You'll just have to be more creative about it.

Use what you know about your friends' habits, projects, hobbies and needs to try getting them together. Here are a few suggestions:

- If Jane's struggling to get through spring cleanup of her yard on her own, and John's the kind of guy who doesn't mind helping out a friend of yours on a Sunday afternoon, set up a day for him to help her out. Or maybe Jane's already got her mowing and debris removal under control, but John's yard needs a woman's touch and she's an avid gardener.

- Computers are a great way for people to meet, and not just through chat rooms and dating sites. Everyone needs a little PC help now and then. Did Jane's ex always take care of her standard computer maintenance? Maybe John can give her a how-to on doing it herself. Is John trying to start up a web site or learn a new accounting program for his side business? Jane might be just the person to help him out.

- Get them together to help you with something. Maybe Jane and John are both computer whizzes, and you're the one who needs some guidance. Maybe it's your yard or garden that's struggling, and each brings a talent to the table that could help you out.

In general, look for things they might have in common. Stretch your imagination. Maybe they're both dealing with caring for aging parents and could share resources. Maybe he writes and needs a good editor to look over some things he's thinking about publishing. Maybe John just went through buying a home, and now Jane's looking in the same community and he can give her some pointers.

To Tell or Not to Tell

So, you're about to play matchmaker. You've decided they're perfect for each other and you've planned an event. You've extended the invites and everyone is coming. So, do you tell one or both members of your intended love match what you really have in mind?

That's entirely up to you. You'll need to consider their personalities and make the best decision. Here are a few things to ask yourself before you decide:

- What are their feelings on matchmaking? Are they open to the idea, or are they the type to run screaming from the mere suggestion? Will knowing you've thought about them as a potential match encourage them to check each other out more, or will it set up an automatic mental road block?

- Would telling her (or him) be more likely to make her nervous and awkward or encourage her to take that little added extra effort to look and feel her best before she arrives at your place?

If you decide to share your evil genius with one or both of them, make sure you do it in a way that keeps them comfortable. Make it clear that you're not "really" matchmaking, you're just getting some friends together and it occurred to you that the two of them meeting might be a good thing. There will be others around, and no pressure. Your feelings won't be hurt if she doesn't like him. He won't have to feel awkward or on the spot, you're just having a gang over for a friendly game or trying to get your girlfriend some help with her finicky PC.

Matchmaking in adulthood is both an adventure and a challenge. In some ways it's like putting the pieces of a puzzle together. Remember that your role is to put them in the same place and then back off and see what happens. It'll be up to them to decide if the pieces actually fit.