1. Don't Assume, Presume, or Project
If you have a single friend in the 27-34 age range, they probably fall into one of two buckets (unless they are recently divorced or broken up). They are either what Nelly Furtado would call "promiscuous" or they are perpetually single. If the friend is in the former camp, don't just assume that they don't want a relationship, unless they have specifically told you that. Some people play the "waiting for the right one" game, and as they say, "if you can't be with the one you love, love the one you're with."
That being said, don't project on this person either. It may be a case that they don't want to settle down now or perhaps ever. Not everyone wants the white picket fence with the 2.5 children...or even to be married or in a committed relationship. Some people truly embrace the single life, and just because you can't imagine staying single forever (and for the love of god, don't say that sentence to your single friend who is secretly thinking it's about to happen to them), don't assume that others don't want to do so.
2. You May Have Never Been Single...So Deal With It
Literally everyone can remember what it was "like to be single," unless you were in some arranged-at-birth-marriage. We have all been single at some point in our lives. However...some of you haven't really been single as an adult.
Like with all of life, just because it says eighteen on the driver's license doesn't mean that you're an adult, and just because you were broken up from your now wife the summer after sophomore year does not qualify you as having "been single" and therefore can "understand" what it's life for your friend (we've moved on to the "why can't I find the right guy?" friend from the above sample-the playboys don't really need that much help at this point in the rant). A good rule of thumb is that if you haven't been single for a complete six months after you were 25 (and by this, I don't mean you were unmarried-I mean you had no romantic attachments other than random first dates and creepy old guys hitting on you at a bar), it's safe to assume you've never been single as an adult. The reason for this is that you aren't really single in your early twenties, because even if you're dating someone you're still spending all of your time with friends in college, first jobs, parties, etc. After 25, you get a taste of proper adulthood, and you don't have friends crashing at your house on a regular basis or you don't have a roommate, and therefore you get a taste of the "alone" of singledom.
3. If You Don't Have Anything Constructive to Say, Don't Say Anything at All
If your friend is indeed in this age range and they say some variant of "it's so hard to find someone" or "I'll never find someone," do not follow with the following words: "you just haven't met the right person yet, but he/she's out there." There is literally nothing worse to say. Are you listening? DON'T SAY IT.
And here's why: when you've been on more first dates or blind dates than you can count, it's hard not to blame yourself. In fact, it's almost impossible not to if you have been genuinely trying to find "the one" for a number of years. Having your happily married-to-their-college-sweetheart friend state that "he's out there" when they met the man of their dreams at twenty is a bit like pushing someone into the snow and then asking why they're in the snow.
4. For the love of God, Offer to Help
Instead, be genuinely helpful-ask about online dating and if they've tried it (online dating is a bit like having a root canal, but like a root canal it can occasionally be very beneficial, so this isn't the worst idea in the world). Or some sort of matchmaker service. Offer up a friend from work or your spouse's gym buddy. Or just be a shoulder to cry on and ask "how can I help?" if you've run out of solutions.
And then, and here's the big one-follow through with it. Because while I know that married people and parents of new children have to deal with a whole mess of their own issues, there are support structures in place for them to succeed. When you have a problem and have a spouse, you have someone who is there to support you. Grandparents love volunteering to take care of new children. And yet, single people sometimes need help too-adulthood gets more complicated regardless of your personal life as you get older, and without any single friends to go clubbing with, sometimes you sort of give up-no one wants a friend to be unhappy, and if they are unhappy because they have trouble with this aspect of their lives, remember all of the times they were there for you and get up and volunteer. I cannot stress this enough-if you have a single friend who talks about finding the one enough, for the love of pizza, ask if there's anything you can do to help.
5. If Need Be, Push Your Friend Out of Their Comfort Zone
This is a big challenge on occasion, but as you get older, you start to become so relaxed in your day-to-day life that you need a push. This is specifically for the friends of the single people who complain all-the-time about being single, but (in your eyes) never actually do anything about it. They don't go to the bars, they don't speed date, they don't have an eHarmony profile, and they say no to every set-up. Depending on the situation, this may be a truth-telling time ("I love you, you're wonderful, but if you rule out every guy who isn't Channing Tatum you're going to be screwed, and not in the way you want").
But, remember they're your friend, and give going out to the bar a try-recruit a few people and have them go out. And remember what you're there for-don't get bogged down in a three-hour catch-up conversation or invite another friend who isn't friends with your single friend along, and then have them whine about how boring the gay bar is and can we go dancing instead so you end up spending twenty minutes at that bar and then end up spending the rest of the night at a cowboy bar where there is literally no other gay person (...for example). And finally, remember that this night is not about your ego-the point is not to spend the evening saying, "I'm flattered, but I'm married"-it's to get your friend some action.
6. Rules of Thumb on Setups
I mentioned it above a bit, but I just want to provide some ground rules on setups. Setups are tricky for all involved, including the person who is doing the setup. For starters, don't set up someone who is major drama with someone who isn't, and don't randomly set up someone because they're single and the same age or the same sexuality. If you genuinely think they might hit it off, then go for it.
However, unless you have a strong objection (ie your friend is more drama than they realize), you need to do two things: one, you need to give an actual reason for not setting them up when your friend has the guts to ask if you have any single friends, and not just say "I just don't see you two together." Because that snow analogy I listed above doubles for that specific comment. Give actual, tangible reasons for this, particularly if your friend is perpetually single and hasn't brought home a lot of gf's/bf's for you to meet (and therefore you have no idea what their type is, regardless of what you assume).
And lastly, unless you have super strong objections, if they actually know the person that you're trying to set them up with, don't assume that you know they won't hit it off. You don't have to set them up on a date proper, but at least give your friend a shot-have a group hangout with a bunch of people so your friend can get over the crush when he hits on someone ten years younger than him or perhaps, they'll meet the person of their dreams. Meeting single people is hard-don't bogart them if you have a plethora stored away.
And those are my thoughts today on helping your single friends out. In the comments, list some other pointers, and even better, list something you did or are planning on doing for your single friend this week!
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